Guistrigona Vacation Rentals
Caiano
Amazing private villa with WIFI, private pool, TV, terrace and panoramic view
Special Offer-
8
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4
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2
Description
Property Summary
Nestled 750 meters above sea level in the heart of Tuscany, Italy, Caiano is a charming and rustic holiday rental that invites you to slow down and reconnect with the natural world. Surrounded by trees, rolling fields, and vineyards, this distinctive property offers a genuine sense of seclusion without sacrificing access to the region's most celebrated destinations. Located just 7 kilometers from the center of Cavriglia, Caiano strikes an ideal balance between peaceful countryside living and everyday convenience. The property features a private fenced terraced garden of 1,000 square meters, a seasonally available swimming pool, and ample parking for up to 3 cars directly on the premises. Wireless internet connection is available throughout, ensuring you remain connected whenever needed, while the generous yard and surrounding natural landscape provide an exceptional setting for a truly restorative stay.
Outdoors
The outdoor spaces at Caiano are among its most defining and memorable features. The private terraced garden, spanning 1,000 square meters, is fully fenced to ensure your privacy and security, creating an intimate and sheltered environment in which to relax and unwind. Within the garden, you will find a wildlife garden with mature trees, a natural garden area, and an open meadow, all contributing to the property's rich and unspoiled natural character. The swimming pool, available seasonally from May 1st to September 30th, features an unconventional shape that adds a distinctive charm to the outdoor setting. An outdoor shower is conveniently located nearby for use after a swim. A terrace completes the exterior offering, providing an ideal space for outdoor dining, relaxing in the fresh Tuscan air, or simply taking in the surrounding landscape of vineyards and countryside.
Other Information
A car is recommended to fully enjoy everything that Caiano and its surrounding area have to offer, given the property's elevated and rural position. The nearest shop is located 4 kilometers from the property, while a supermarket can be found 8 kilometers away, making it easy to stock up on local produce and essentials during your stay. Guests should be aware that the swimming pool is available on a seasonal basis, operating from May 1st through September 30th.
Distances and Attractions
Caiano enjoys a privileged position that places some of Tuscany's most celebrated towns and attractions within easy reach. The center of Cavriglia is just 7 kilometers away, while the renowned wine town of Radda in Chianti lies 8 kilometers from the property, offering excellent opportunities to explore the Chianti Classico wine region, its historic villages, and its outstanding local gastronomy. The iconic city of Siena, with its world-famous Piazza del Campo, Gothic cathedral, and vibrant cultural scene, is located 38 kilometers away, making it an ideal destination for a day trip. For those traveling by train, the nearest railway station is San Giovanni Valdarno, situated 12 kilometers from the property, providing convenient rail connections to Florence and other major Tuscan cities. Caiano
Gaiole in Chianti 880
Unique multi-unit holiday villa with WIFI, pool, TV, patio and pets allowed
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9
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47
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24
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15
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| La Colomba N°4 880.1 | 4 | 2 | 2 | 75 m2 | € 107 /Night |
| La Farfalla N°5 880.2 | 4 | 2 | 1 | 75 m2 | € 99 /Night |
| Pulcino N°3 880.3 | 2 | 1 | 1 | 32 m2 | € 57 /Night |
| Il Pettirosso N°7 880.5 | 4 | 2 | 1 | 55 m2 | € 91 /Night |
| Coccinella N°6 880.6 | 4 | 2 | 1 | 50 m2 | € 99 /Night |
| Cerbiatto N°5A 880.7 | 2 | 1 | 1 | 35 m2 | € 51 /Night |
| Il Gufo N°1 880.9 | 13 | 7 | 4 | 180 m2 | € 317 /Night |
| Il Ghiro N°8 880.4 | 4 | 2 | 1 | 65 m2 | € 99 /Night |
| Lo Scoiattolo N° 10 880.8 | 10 | 5 | 3 | 115 m2 | € 229 /Night |
| All 9 Accommodations | 47 | 24 | 15 |
Description
Property Summary
Nestled in the rolling Tuscan countryside of Cavriglia, Italy, Podere La Massa is a carefully renovated property comprising a detached house and eight apartments, each offering a private outdoor area enclosed by natural hedges. Surrounded by ancient olive groves and open fields, this exceptional holiday rental commands a stunning view of the iconic Chianti hills, making it an ideal retreat for nature lovers who appreciate long walks or leisurely bike rides through the surrounding landscape. The property sits in a secluded and elevated position, ensuring a sense of tranquillity and privacy that is rarely found elsewhere. Guests benefit from WiFi available throughout the entire property, keeping you effortlessly connected while you unwind in this peaceful rural setting. A generous shared natural garden of 2 hectares provides ample space to relax and explore, while the impressive swimming pool, measuring 14 x 7 metres with a depth ranging from 100 to 250 cm, invites you to cool off and enjoy the warm Tuscan seasons.
Outdoors
The outdoor spaces at Podere La Massa are thoughtfully designed to complement the natural beauty of the surrounding Chianti countryside. The swimming pool, available seasonally from May 6th to September 30th, is accompanied by an outdoor shower for your convenience, and the surrounding area is furnished with garden furniture ideal for sunbathing or simply soaking in the panoramic views. Families travelling with children will appreciate the dedicated playground, complete with a slide, while sports enthusiasts can enjoy the on-site volleyball court. Each apartment benefits from its own private outdoor area, carefully fenced by hedges to ensure a comfortable degree of seclusion, allowing you to enjoy the fresh country air in a more intimate setting. The shared 2-hectare natural garden further extends the outdoor experience, offering open green spaces framed by olive groves and the gently undulating Chianti hills.
Other Information
Podere La Massa offers a number of practical amenities to ensure a comfortable and well-organised stay. A shared washing machine is available on-site for guest use. Heating is provided seasonally from November 1st to April 15th and is payable directly on-site. Fresh bread rolls can be arranged upon request, adding a charming local touch to your mornings. The property also offers local farm products for sale, giving you the opportunity to take a taste of authentic Tuscan produce home with you. Access to the property is by motor vehicle, with the final 4 km of the approach via an unmade road, and parking is available on-site at no additional inconvenience. It is strongly recommended that guests have a car at their disposal for the duration of their stay, as the nearest shop and restaurant are both located 5 km from the property.
Distances and Attractions
Podere La Massa enjoys a privileged position in the Chianti countryside, offering easy access to some of Tuscany's most celebrated towns and attractions. The centre of Gaiole in Chianti is located 10 km away, while Radda in Chianti can be reached within 13.5 km. The Montevarchi railway station is 10 km from the property, providing a convenient transport link for those wishing to explore the wider region. The historic city of Siena lies 43 km away, and the world-renowned city of Florence is within reach at 65 km. Among the many nearby points of interest, Castelnuovo Berardenga is 19 km away, Castellina in Chianti is 24 km, and both Greve in Chianti and San Donato are approximately 30 km from the property. Badia a Passignano, a remarkable Benedictine abbey surrounded by vineyards, is 34 km away, while the medieval hilltop town of San Gimignano is 52 km distant. For those seeking relaxation beyond the property itself, the Rapolano Terme thermal baths offer a rejuvenating experience just 45 km away. The nearest shop and restaurant are both conveniently situated 5 km from Podere La Massa. Gaiole in Chianti 880
San Giovanni 801
Lovely flat with WIFI, pool, TV, terrace and pets allowed
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4
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21
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8
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4
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Girasole 801.1 | 4 | 1 | 1 | 54 m2 | € 130 /Night |
| Lavanda 801.2 | 6 | 3 | 1 | 70 m2 | € 156 /Night |
| Rosmarino 801.3 | 5 | 2 | 1 | 110 m2 | € 159 /Night |
| Corbezzolo 801.4 | 6 | 2 | 1 | 210 m2 | € 205 /Night |
| All 4 Accommodations | 21 | 8 | 4 |
Description
Property Summary
Nestled at an elevation of 150 meters above sea level in the serene Tuscan countryside of Cavriglia, Italy, Manor House "Filicaia" is an exceptional vacation rental that combines rural tranquillity with refined comfort. The property comprises 5 individual apartments set within a quiet and sun-drenched landscape, offering guests an authentic experience of the Italian countryside. Throughout your stay, you will benefit from a range of carefully considered amenities designed to enhance your comfort and relaxation. The expansive yard surrounding the property provides a peaceful natural setting where you can unwind and immerse yourself in the beauty of the Tuscan hills. A shared swimming pool is available for guests to enjoy during the warmer months, offering a refreshing retreat after a day of exploration. For those who need to remain connected, high-speed internet WiFi is provided throughout the property, ensuring seamless connectivity without compromising the sense of escape that Manor House "Filicaia" so effortlessly delivers.
Outdoors
The outdoor spaces at Manor House "Filicaia" have been thoughtfully arranged to offer guests a complete al fresco experience in the heart of the Tuscan countryside. The shared swimming pool measures 12 x 6 meters with a depth ranging from 120 to 200 cm, and is available for seasonal use from 07 May to 24 September, providing ample opportunity to enjoy the warm Italian summer. Complementing the pool area, an outdoor shower is conveniently available for guests returning from a swim. The garden is furnished with outdoor furniture, creating a welcoming space where you can relax, dine, and socialise in the open air. A barbecue is also at your disposal, inviting you to make the most of the long Tuscan evenings with al fresco dining surrounded by the natural beauty of the countryside.
Other Information
To ensure a comfortable and well-organised stay at Manor House "Filicaia," several practical amenities and house policies are in place for your convenience. A washing machine is available for shared use among guests, making longer stays particularly comfortable. Heating is provided seasonally, available from 01 November to 07 April, and is subject to an additional charge. Private parking is available directly on the premises, offering ease of access for guests arriving by car. Please be aware that the owner of the property resides on the same premises, which ensures attentive and responsive hospitality throughout your visit.
Distances and Attractions
Manor House "Filicaia" enjoys a privileged position in the Tuscan countryside, placing you within easy reach of some of the region's most celebrated destinations and attractions. The centre of San Giovanni Valdarno is just 3.8 km away, offering a convenient base for everyday needs including shops, restaurants, and local services. For those wishing to explore the renowned Chianti wine region, the centre of Gaiole in Chianti is approximately 18 km from the property, while Radda in Chianti lies at a distance of 26 km. Further afield, the historic Castello di Meleto, the charming villages of Greve in Chianti, Castellina in Chianti, and Panzano in Chianti are all within comfortable driving distance, each offering a unique glimpse into the rich cultural and viticultural heritage of Tuscany. For those seeking the grandeur of Italy's most iconic cities, the art-filled streets of Firenze and the medieval splendour of Siena are both easily accessible by car, making Manor House "Filicaia" an ideal base from which to discover the very best of this extraordinary region. San Giovanni 801
Trequanda 810
Unique multi-unit villa with WIFI, pool, TV, patio and panoramic view, close to Montepulciano
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3
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10
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5
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4
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Geranio 810.1 | 4 | 2 | 2 | 70 m2 | € 185 /Night |
| Focolare 810.2 | 4 | 2 | 1 | € 163 /Night | |
| All 2 Accommodations | 8 | 4 | 3 |
Description
Property Summary
Nestled in the rolling Tuscan countryside of Trequanda, Italy, the charming rustic farmhouse "Podere La Fonte" offers an authentic and tranquil retreat surrounded by trees, fields, and vineyards. This holiday rental is part of a small residence comprising 4 apartments, each individually designed and furnished to reflect the character and warmth of the local rural tradition. Situated just 1 km from the centre of Trequanda and set in a secluded, quiet position approximately 100 m from the edge of the forest, the property provides a genuine sense of privacy and immersion in the natural landscape. Guests have shared access to a generously sized swimming pool measuring 12 x 5 m, available seasonally from 15 May to 15 October and enclosed for safety, with pool maintenance carried out by the owner or gardener. The expansive yard extends across a natural state property of approximately 3 ha, incorporating garden plants and trees as well as a productive orchard. A tennis court and volleyball court are available for shared use, offering excellent recreational opportunities without leaving the estate. Wireless internet connection is available, ensuring guests remain connected throughout their stay. Baby equipment is included for families travelling with young children, and local farm products are available for sale directly on the premises. The owner resides within the same residence, ensuring attentive and personalised hospitality throughout your visit.
Outdoors
The outdoor spaces at "Podere La Fonte" are expansive and thoughtfully arranged to make the most of the stunning Tuscan surroundings. The shared fenced swimming pool, measuring 12 x 5 m, is open seasonally from 15 May to 15 October and is complemented by an outdoor shower for the convenience of guests. A patio and terrace provide ideal settings for relaxing or dining in the open air, furnished with garden furniture suited to outdoor meals and leisurely afternoons. A barbecue is available for shared use, perfect for enjoying long summer evenings in the countryside. The tennis and volleyball court offer additional outdoor recreation, while the orchard and mature garden with trees and plants create a lush and peaceful environment. The property is accessed via a 600 m long narrow motor road leading to the grounds, and parking is available directly on the premises.
Other Information
A washing machine is available within the house for shared use and is subject to an additional charge. Guests are advised that a car is strongly recommended in order to access the property and its surroundings comfortably. Animals are present in the neighbourhood, which contributes to the authentic rural character of the estate. All apartments within the residence are individually designed and furnished, ensuring a distinctive and personal atmosphere in each unit.
Distances and Attractions
"Podere La Fonte" benefits from a convenient location that places a wide range of everyday amenities and cultural destinations within easy reach. A shop, grocery store, restaurant, bar, and bakery are all located approximately 1 km away, while the nearest supermarket is 9 km distant and a shopping centre can be reached within 15 km. The bus stop for Trequanda is 1 km from the property, and the railway station of Sinalunga is 9 km away. For those seeking relaxation and wellness, the renowned thermal baths of "Rapolano Terme" are situated 23 km from the estate. Nature enthusiasts will appreciate the proximity of the bathing lake "Trasimeno," reachable in approximately 40 km, one of the well-known lakes of the region that can easily be reached from the property. A 9-hole golf course is located 16 km away, and a riding stable is just 5 km from the farmhouse. The surrounding area is rich in cultural and historical heritage, with the celebrated towns of Pienza at 17 km, Montepulciano at 22 km, Cortona at 35 km, and the magnificent city of Siena at 55 km all within comfortable driving distance. Trequanda 810
Tribolina
Wonderful independent villa with WIFI, TV, pets allowed and panoramic view
Special Offer-
4
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2
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2
Description
Property Summary
Manor house "Tribolina" is a captivating vacation rental nestled in the rolling Tuscan countryside of Cavriglia, Italy, perched at 550 meters above sea level atop a sun-drenched hill. This distinguished residence comprises 2 separate houses set within a vast estate of 23 hectares, offering guests an unparalleled sense of privacy and space in one of Italy's most celebrated rural landscapes. The property is just 3 kilometers from the village of Cavriglia, providing the ideal balance between peaceful seclusion and convenient access to local amenities. Guests benefit from reliable internet and Wi-Fi connectivity throughout their stay, ensuring they remain connected without compromising the tranquility of their surroundings. The expansive yard, reserved exclusively for guests, invites leisurely afternoons in the open air, surrounded by the natural beauty of the Tuscan hills. Parking is available directly on the premises, with motor access to the property, though guests should be aware that the final 100 meters leading to the house is via an unmade road.
Outdoors
The outdoor spaces at Manor house "Tribolina" are a true highlight of the estate, offering guests an immersive experience in the unspoiled Tuscan landscape. The natural garden, spanning the property's generous 23-hectare grounds, is maintained exclusively for the use of guests and provides a serene setting for relaxation and outdoor living. Garden furniture is thoughtfully arranged throughout the space, allowing guests to sit back and absorb the panoramic views of the surrounding countryside. A barbecue is also available, making the garden an ideal venue for alfresco dining and convivial evenings under the open sky. The elevated position of the property at 550 meters above sea level ensures that the outdoor areas are bathed in sunlight throughout the day, enhancing the sense of warmth and well-being that defines a stay at this remarkable estate.
Other Information
Heating is available at Manor house "Tribolina" from 1st November to 15th April and is payable directly on the spot upon use. The owner of the property resides on the same estate, ensuring that attentive and personal assistance is always available should any queries or needs arise during your stay. Guests are also invited to take advantage of the local sale of farm products offered on the property, providing a wonderful opportunity to sample and purchase authentic regional produce directly from the source.
Distances and Attractions
Manor house "Tribolina" enjoys an exceptionally well-connected location within the Tuscan countryside, placing a wealth of cultural, culinary, and natural attractions within easy reach. The village of Cavriglia is just 3 kilometers away, while the town of Montevarchi can be reached in approximately 12 kilometers. The historic city of Florence lies 65 kilometers from the property, making it an accessible destination for a day of art, architecture, and gastronomy. For lovers of fashion and design, the Prada outlet is located just 14 kilometers away, and The Mall outlet is also conveniently reachable from the estate. The charming Chianti wine villages of Gaiole in Chianti and Radda in Chianti are situated 9 kilometers and 12 kilometers away respectively, offering scenic drives through vineyards and medieval hilltop towns. The celebrated cities of Siena and Arezzo are equally accessible, each offering a rich tapestry of history and culture. For those seeking relaxation and wellness, the Rapolano Terme thermal baths are located 50 kilometers from the property, providing a restorative retreat within the broader Tuscan region. Tribolina
Villa Pietrafitta
Superb independent vacation rental with private pool, WIFI, TV and patio, close to Greve In Chianti
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12
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6
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6
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200 m2
Description
Conveniently located 5 km (3 mi) from Castellina In Chianti, Italy in the tourist area "Siena And Surroundings" and only 17 km (11 mi) from Greve In Chianti. Villa Pietrafitta is a nice stone building (200 sq m) with WiFi internet and private pool. The property can accommodate up to 12 people comfortably in six bedrooms with six bathrooms.
Your Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outdoors are a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished patio where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 17 km (11 mi), Siena 26 km (16 mi), San Gimignano 33 km (20 mi), Florence 46 km (28 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 46 km (28 mi), Viareggio 140 km (87 mi), Forte Dei Marmi 147 km (91 mi), Rome 267 km (166 mi), Milan 340 km (211 mi) and Naples 458 km (284 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:00 - 10:00
Pool Open: 3 May - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 59 km (36 mi), Pisa (psa) 105 km (65 mi), Bologna (blq) 145 km (90 mi), Roma Ciampino (cia) 276 km (171 mi) and Genova (goa) 278 km (173 mi).
Additional Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a pleasant way to spend time with friends and family while discovering the techniques needed to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the extra costs.
The garden is fully enclosed. Villa Pietrafitta
Fantastic holiday home with private pool, A/C, WIFI, balcony and panoramic view, close to Siena
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12
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6
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6
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800 m2
Description
Medieval Castle Living: Vineyards, Swimming Pool & is a nice stone building (800 sq m) with private pool, WiFi internet and air conditioning. The property can sleep up to 12 guests comfortably in six bedrooms with six bathrooms. Medieval Castle Living: Vineyards, Swimming Pool & is located 4 km (2 mi) from Sovicille, Italy and only 14 km (8 mi) from Siena in the tourist area "Siena And Surroundings".
Nestled in the lush greenery of the Montagnola Senese, this magnificent property is a masterfully preserved 13th-century castle located just a 15-minute drive from the historic heart of Siena. The estate has been meticulously restored by its owners, who reside in the main tower in a secluded area that remains entirely private and separate from guest accommodations.
The estate is thoughtfully designed to offer both community and privacy. The first floor of the main castle features two charming apartments. Adjacent to the castle is a separate cottage housing two additional apartments, providing an ideal retreat for couples or guests seeking extra seclusion. With fully equipped kitchens in every unit and expansive common areas, the property perfectly balances independent living with shared moments.
Surrounded by rolling vineyards producing a refined selection of "Super Tuscan" wines, the estate invites you to embrace the slow pace of Italy. The grounds are a masterpiece of landscape design, featuring manicured lawns, traditional terracotta planters, and vibrant blooms. At the heart of the garden lies a generous swimming pool, fully outfitted with elegant sun loungers and umbrellas.
This elegant and spacious holiday home is perfectly suited for a luxurious escape with family or friends. The property comfortably accommodates up to twelve guests (with capacity for an additional two guests upon request).
Your Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a playground and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished balcony where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 14 km (8 mi), San Gimignano 46 km (28 mi), Montalcino 49 km (31 mi), Greve In Chianti 53 km (33 mi) and Montepulciano 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 170 km (105 mi), Forte Dei Marmi 177 km (110 mi), Rome 248 km (154 mi), Venice 322 km (200 mi) and Milan 372 km (231 mi).
Additional Information
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 88 km (55 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 257 km (160 mi) and Roma Fiumicino (fco) 270 km (168 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques vital to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while learning the secrets required to prepare mouth-watering Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the supplemental costs.
Meals - If you'd like to have meals provided during your stay, either half-board or full-board is available. If you prefer only breakfast be provided, that can be arranged as well. Inquire about the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Exclusive Estate Inclusions : elevate your stay, we offer these bespoke services upon reservation:
When you choose the Castle Experience, your stay includes a curated selection of authentic local luxuries:
- Gourmet Farm-to-Table Breakfast: Start your morning in the castle’s elegant common wing with a signature breakfast prepared by the Castellana (the Lady of the Castle). Every ingredient is organic and locally sourced ("Km 0"), with each dish prepared à la minute to your preference upon your arrival at the table.
- Estate Wine Tasting: Enjoy an exclusive guided tour of the castle with a private tasting in the castle’s historic cellar. This experience can be scheduled at your convenience with a simple advance reservation.
Bespoke Guest Experiences (Optional)
To further enhance your Tuscan retreat, we are pleased to arrange the following premium services:
- Dining with the Castellana: Enjoy an elegant, candlelit dinner hosted in the castle's private courtyard—an intimate glimpse into authentic noble life.
- Culinary Arts: Participate in private cooking classes or enjoy professionally catered buffet dinners.
- Outdoor Adventures: Explore the region with curated wine tours, guided bike excursions, or scenic hiking trips through the Montagnola Senese.
- Tuscan Traditions: Experience the thrill of a professional truffle hunting.
Medieval Castle Living: Vineyards, Swimming Pool &
Podere della Crocchia
Unique private villa rental with private pool, WIFI, TV and pets allowed, near Arezzo
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8
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3
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2
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120 m2
Description
SPECIAL OFFER 10% DISCOUNT FROM 26 September To 3rd October 2026 – FOR 1-WEEK BOOKINGS
Podere della Crocchia, a beautiful old stone villa in a very panoramic position, is immersed in a rural environment that embodies all the characteristics of typical Tuscan landscapes. Looking out over the valley you will see endless expanses of cereal, corn and sunflower fields, which blend in harmony with the high hills. The ancient villages, manor houses and farmhouses surrounded by vineyards and olive groves will immerse you in a dreamlike atmosphere. The owners themselves, Luca and Patrizia, in addition to excellent organic extra virgin olive oil, wine and other fine goods, also produce a natural food supplement based on olive leaf extract.
The villa is a combination of old, modern and hospitality: stylish furnishings and all the necessary comforts and facilities. In the cool pergola, in front of the kitchen, equipped with wooden furniture and barbecue, you can relax and dine al fresco. If you are looking for a villa with hotel services, Podere della Crocchia is the right place for you. Our guests are enthusiastic about the extras offered by the very friendly owners (starter pack of detergents, tea, coffee, sugar), fresh vegetables, homemade cakes, welcome drink... and consider them one of the bonuses of the villa.
In the wide garden you can spend your leisure days thanks to the beautiful private swimming pool (size mt. 6x12, depth mt. 1.20-1.80 - open from 01st April to 30th September), with comfortable wooden sunbeds, table tennis and games for children. In the surrounding area there are many paths suitable for cycling or trekking, with children as well, in the wonderful Tuscan landscape. Podere della Crocchia
Villa Aiale
Beautiful private house with A/C, WIFI, private pool, TV, patio, panoramic view, near Montalcino
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14
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7
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8
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500 m2
Description
Villa Aiale is a beautiful property (500 sq m) with air conditioning, WiFi internet and private pool. The property can sleep up to 14 people comfortably in seven bedrooms with eight bathrooms. Conveniently located 2 km (1 mi) from Bibbiano, Italy in the tourist area "Orcia Valley" and only 21 km (13 mi) from Montalcino.
The Experience
When you arrive at Villa Aiale you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. Outside you will also find a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 21 km (13 mi), Siena 38 km (24 mi), Montepulciano 53 km (33 mi), Arezzo 77 km (48 mi) and Cortona 78 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 106 km (66 mi), Viareggio 200 km (124 mi), Forte Dei Marmi 207 km (129 mi), Rome 229 km (142 mi), Milan 400 km (249 mi) and Naples 420 km (261 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 119 km (74 mi), Pisa (psa) 154 km (96 mi), Bologna (blq) 205 km (128 mi), Roma Fiumicino (fco) 232 km (144 mi) and Roma Ciampino (cia) 238 km (148 mi).
More Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a enjoyable way to spend time with friends and family while learning the techniques vital to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the supplemental costs.
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Maid Service - If you'd like maid service during your visit that can be organized by the owner. Inquire for more details about the additional cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the supplemental cost and how to arrange this service.
Villa Aiale
Villa le Caggia
Stunning independent property with WIFI, private pool, A/C, hot tub, TV, patio, close to Siena
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16
-
7
-
7
-
500 m2
Description
Property Villa Le Caggia is a beautiful stone building (500 sq m) that includes air conditioning, WiFi internet and private pool. The property can sleep up to 16 guests comfortably in seven bedrooms with seven bathrooms. Villa Le Caggia is located 6 km (4 mi) from Arnano, Italy and only 19 km (12 mi) from Siena in the tourist area "Siena And Surroundings".
The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a splendid vacation in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of shopping. Outdoors you will also find a hot tub, barbecue grill, patio and playground. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 16 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 19 km (12 mi), San Gimignano 33 km (20 mi), Greve In Chianti 53 km (33 mi), Montalcino 55 km (34 mi) and Florence 68 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (43 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 170 km (106 mi), Rome 254 km (158 mi), Venice 319 km (198 mi) and Milan 362 km (225 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Le Caggia. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 15:00 - 22:00
Check-Out Time: 00:00 - 10:00
Pool Open: 15 March - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 83 km (52 mi), Pisa (psa) 116 km (72 mi), Bologna (blq) 168 km (104 mi), Roma Fiumicino (fco) 250 km (155 mi) and Roma Ciampino (cia) 264 km (164 mi).
Special Services
Cooking Lessons - Learn from a local chef the techniques needed to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while discovering the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be organized by the owner. Inquire for more details about the additional cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Ask for more details, including the additional cost and how to schedule this service.
The villa is equipped with an electric fence that is activated at night to protect the outdoor areas from wild animals.
Pets are welcome (even more than one), but we cannot guarantee that dogs will not wander off. Villa Le Caggia
La Quiete
Amazing private property with WIFI, private pool, TV and pets allowed, near Arezzo
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16
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8
-
4
-
400 m2
Description
La Quiete is a very old farmhouse that preserves intact the characteristics of the rural architecture. The villa is lovingly preserved by its owners, and if you are lucky enough to stay here, its wooden ceilings, ancient brick arches, Tuscan terracotta floors and elegant furnishings will welcome you into a very special charm, made of old, simple and essential things. At La Quiete you will feel at home, in a warm and cosy atmosphere.
The villa is located at the foot of the first wooded hills, which mark the border between Valdichiana and Valdarno, from here you can make even daily excursions, towards the two valleys, dotted with small villages nestled in the Tuscan countryside. In Monte San Savino, which is just a few kilometres away, it will be pleasant to spend evenings out, dining in typical restaurants or enjoying an aperitif sitting at tables in the colourful cobbled streets.
From the windows of the villa you can admire the imposing Castello di Civitella with its characteristic 'Torre Spaccata'. We absolutely recommend a visit to this small village, a real jewel of the Valdichiana, with its ancient cistern, panoramic square and medieval buildings.
La Quiete, in our opinion, is perfectly suited for your holidays with children, or in the company of large groups of friends. Around the house you will find a large green area equipped with outdoor furniture, barbecue, table tennis, table football, children's games, volleyball court and five-a-side football pitch. A splendid swimming pool (size 6x12 m, depth 1.10-2.00 m - open from 01st May to 30th September) will brighten your summer days, and the large furnished portico outside will be the setting for your breakfasts, lunches and dinners in the open air. La Quiete
Villa la Guardiola
Amazing independent villa rental with A/C, WIFI, private pool, TV and pets allowed, near Arezzo
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10
-
5
-
3
-
320 m2
Description
Villa La Guardiola is a charming residence nestled in the heart of the Valdichiana, just 2 km from Civitella in Valdichiana, the ideal place for a relaxing getaway surrounded by beautiful nature, without sacrificing modern comforts.
The villa is a haven of tranquillity and beauty, consisting of a large farmhouse with finely restored stone outbuildings that can accommodate up to 10 people. It is perfect for families or groups of friends looking for a refined and exclusive retreat. The atmosphere is typical of ancient Tuscan residences: large, bright rooms and elegant furnishings that preserve the authenticity of tradition, but with all the comforts of today.
The villa is located in a unique position, immersed in a park shaded by tall trees and surrounded by the picturesque vineyards that characterise the Tuscan countryside. The view over the valley is breathtaking, while the outdoor area, perfect for relaxing, sunbathing or dining al fresco, offers spectacular views, with the sunset painting the sky above the hills like a painting.
Just a few minutes from the picturesque village of Civitella in Valdichiana, famous for its history and its split tower, the villa is strategically located for exploring the beauty of Tuscany. Art cities such as Siena, Arezzo and Florence are easily accessible by car, while supermarkets, shops and excellent local restaurants are less than 5 km away.
Villa La Guardiola offers a splendid private enclosed swimming pool (4x8 metres, depth 1.15 metres - open from 01/05 to 30/09) where you can take a refreshing dip on hot summer days, enjoying maximum privacy and tranquillity. The surrounding park is the ideal setting for a totally relaxing stay.
Furthermore, as it is an integral part of the winery, you will have the opportunity to explore the vineyards, discover the winemaking processes and participate in exclusive tastings. A unique food and wine experience to savour the best wines of the area.
Villa La Guardiola is the ideal starting point for discovering the culture, flavours and traditions of Tuscany. With its privileged location, the beauty of its spaces and its proximity to places of historical and artistic interest, it is the perfect choice for a holiday that combines relaxation, nature and authentic Tuscan experiences. Villa la Guardiola
Villa Crispinino
Unique private holiday rental with WIFI, private pool, A/C, patio, panoramic view, close to Arezzo
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9
-
4
-
4
-
400 m2
Description
This is an independent villa boasting beautiful views and its own swimming pool. Its dominating position, overlooking the Val di Chiana, is not far from the town of Civitella.
The villa itself has been recently refurbished however, it still holds its original character such as terracotta floors, wooden beams and stone arches.
Outside there is a large terrace and a large garden, both offering privacy and somewhere to relax in the open air. The property is surrounded by fencing.
Villa Crispinino is perfectly positioned for anyone hoping to visit Tuscany’s famous sites. About 20 km from the property, in the town of Arezzo, you can catch a train to destinations such as Rome, Florence, Orvieto and Siena.
Access to the property is via a dirt road (in great condition).
Distances: The nearby town of Civitella (4 km) can offer you food shops while Battifolle (10 km) can offer a large selection of shops. Arezzo lies 20 km away and slightly further afield are the cities of Siena (50 km), Florence (80 km), Assisi and Perugia (90 km).
Available to guests: Large, well-kept and furnished garden, swimming pool reserved exclusively for guests (10 x 5 m - depth 1.4 m) and barbecue.
The rental has free WI-FI and a Play Station.
Parking available on the grounds of the property.
Extra Services: Upon request, two children’s cots are available at no extra charge.
Please carefully check if there are any extra costs to be paid on site! Villa Crispinino
La Capanna di Franca 6+2
Superb villa rental with WIFI, private pool, A/C, TV, terrace and pets allowed, close to Siena
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8
-
3
-
3
-
142 m2
Description
Property Summary
Nestled within the medieval hamlet of Palazzavelli, just one kilometre from the centre of Sovicille in Tuscany, Italy, La Capanna di Franca is a beautifully restored stone farmhouse that offers an exceptional vacation rental experience for those seeking authentic rural charm combined with modern comfort. Originally an old barn, this characterful country house was meticulously transformed in 2006 through careful restoration work that preserved and celebrated its original architectural style, resulting in a warm and inviting retreat that harmoniously blends rustic heritage with contemporary living. Set in an independent position within a lush garden of approximately 5,000 square metres, the property enjoys breathtaking views from the first floor windows over the surrounding Tuscan countryside, with the city of Siena visible in the distance. Guests benefit from private parking accessed via a driveway bordered by rows of cypresses, complimentary Wi-Fi throughout the property, and a stunning infinity pool set within the beautifully landscaped grounds. The expansive yard, rich with typical Tuscan flora including cork and holm oaks, mulberry and olive trees, palms, pomegranates, roses and broom, creates a serene and private atmosphere that invites relaxation and outdoor living at its finest.
Outdoors
The grounds of La Capanna di Franca are a true celebration of the Tuscan landscape, extending across approximately 5,000 square metres of predominantly lawn-covered parkland. From the entrance gate, a cypress-lined driveway guides you through a well-tended, blooming garden where seasonal flower beds border the stone path leading to the pool area. The atmosphere throughout is quiet and reserved, encouraging guests to spend long hours outdoors. Directly outside the living room French window, a large porch furnished with a table and chairs provides an ideal setting for al fresco dining and leisurely gatherings in the shade. Please note that the garden photographs were taken in spring, and the appearance of the flowers and grass may vary depending on the season of your visit.
The centrepiece of the outdoor space is the magnificent non-heated infinity pool, positioned just 15 metres from the house and immersed in the surrounding garden. Rectangular in shape and measuring 6 x 12 metres, the pool features a border in Tuscan travertine and is internally lined with mosaic tiles, lending it an elegant and distinctly regional character. The depth varies from 1.20 metres to 2.20 metres, and access to the water is made easy via large steps. The pool is equipped with chlorine purification, as well as lighting both inside and outside the water. Along one side, a discreet hedge provides a sense of privacy, while fragrant roses frame the perimeter and a carpet of well-kept lawn surrounds the sunbathing area, which is furnished with sunbeds, an awning, and a hammock. A wooden gazebo with table and chairs completes this outdoor retreat, and an outdoor shower is also available for guests' convenience. The pool is open from the last Saturday in April to the first Saturday in October.
Unit Layout
La Capanna di Franca is configured across 2 floors plus a loft level and is designed to comfortably accommodate up to 8 guests across 3 bedrooms and 3 bathrooms. The ground floor is entered directly from the main entrance and opens into a spacious open-plan living area comprising a lounge with a large fireplace, a dining area, and a fully equipped kitchen. Also on this floor is a study furnished with a single sofa bed, a bathroom with shower, and a dedicated laundry room. A travertine and wrought-iron staircase in the living room leads to the first floor, where 3 bedrooms are located. 2 of these are double bedrooms, one of which features an ensuite bathroom with shower. The third bedroom is a double room with an additional single bed and is served by a separate bathroom equipped with a whirlpool tub. A further flight of stairs ascends to a loft area featuring a super panoramic window and a gym space fitted with exercise equipment.
Amenities Included
La Capanna di Franca is thoughtfully equipped to ensure a comfortable and convenient stay for all guests. Air conditioning is available throughout the property, with the exception of 1 double bedroom, which is instead fitted with a ceiling fan. For cooler months or evenings, heating is available, and the living room fireplace adds an additional layer of warmth and ambience. The kitchen is fully appointed with a dishwasher among its appliances, making meal preparation and clean-up effortless. A washing machine is available in the dedicated laundry room on the ground floor, ensuring practicality for longer stays. Outdoor cooking enthusiasts will appreciate the barbecue facility, perfect for making the most of the property's beautiful garden setting. Entertainment is well catered for with satellite TV, and the property welcomes pets, making it an ideal choice for guests travelling with their animal companions. The property is also connected with internet Wi-Fi, ensuring guests remain connected throughout their stay.
Other Information
Check-in and check-out times, as well as any specific house rules, should be confirmed directly with the property management team. The property welcomes pets, and guests travelling with animals are kindly asked to note that a mandatory extra cleaning fee applies per animal per week or part of a week. Children under 12 years of age are exempt from the tourism tax applicable to the area. The gym area located in the loft is available for guests' use throughout the stay. The infinity pool operates seasonally, from the last Saturday in April to the first Saturday in October, and guests are encouraged to plan their visit accordingly. The property's location within the natural oasis of the Montagnola Senese makes it an ideal base for outdoor activities such as walking, mountain biking, and horseback riding, all accessible directly from the property along woodland trails.
Distances and Attractions
La Capanna di Franca enjoys a privileged position just 1 kilometre from the centre of Sovicille, offering easy access to local amenities while maintaining a sense of peaceful seclusion. The city of Siena, one of Tuscany's most celebrated art destinations, is only a few kilometres away and is visible from the first floor windows of the property. The nearby highway provides swift connections to a wealth of iconic Tuscan destinations, including Cortona, San Gimignano, Florence, Lucca, and Pisa. The surrounding area is also rich in cultural and gastronomic heritage, with the renowned villages of Montepulciano, Pienza, and Montalcino all within reach, as well as the picturesque hamlets of the Chianti wine region. The natural landscape of the Montagnola Senese, which surrounds the property, bears the traces of ancient civilisations and offers a wealth of opportunities for nature lovers and history enthusiasts alike.
Costs & Services
Included services
- Utilities (electricity, water, gas for cooking use): included in the rental price
- Weekly linen change: included in the rental price
- Initial and final cleaning: included in the rental price
- Zer0Dep Guarantee (EuropAssistance coverage for accidental damage up to €1,500.00, with applicable limitations; no security deposit required on balance or on arrival): included in the rental price
Extra costs
- Mandatory extra cleaning in case of animals: €50.00 per animal per week or part of a week
- Tourism tax: €1.50 per person per day for the first 12 days (children under 12 years old are exempt)
On request
- Extra cleaning: €22.00 per hour per cleaner
- Extra linen: €15.00 per person
- Heating: charged on consumption at current market prices
- Firewood: €20.00 per 100 kg La Capanna di Franca 6+2, Emma Villas
Villa delle Upupe 8
Stunning holiday home with WIFI, private pool, TV and pets allowed, close to Greve In Chianti
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8
-
4
-
4
-
165 m2
Description
Property Summary
Nestled in the rolling hills of Tuscany, Villa delle Upupe is an exceptional vacation rental set approximately 2 km from the charming borgo of Castellina in Chianti, Italy. Positioned atop a hill in the heart of the celebrated Chianti Classico region, this beautifully restored farmhouse occupies a privileged vantage point overlooking a breathtaking landscape of olive groves, vineyards, and dense woodland. The property sits within the prestigious Castellare di Castellina estate, a well-established farm covering approximately 80 hectares and renowned for its production of extra virgin olive oil and some of the finest wines in Chianti. The exposed stone exterior gives way to a captivating interior where every room has been designed with meticulous attention to detail, featuring fine furnishings, carefully chosen accessories, and upholstery that evokes the unmistakable hues of the Sienese countryside. The villa benefits from a generous yard that harmoniously blends into the surrounding natural landscape, providing a serene and private outdoor retreat. Connectivity is ensured through Internet WiFi, allowing you to remain in touch while enjoying the tranquillity of the Tuscan countryside. Private parking is available on the property, offering convenience upon arrival and throughout your stay.
Outdoors
The garden surrounding Villa delle Upupe adapts gracefully to the natural slope of the terrain, seamlessly merging with the vineyards, woods, and hills that form its picturesque boundaries. Lavender bushes, wild roses, jasmine, strawberry trees, aromatic herbs, and borders of rosemary frame the dry stone walls and short stone paths, creating a fragrant and visually stunning outdoor environment. A panoramic pergola positioned just outside the living room French windows provides an ideal setting for relaxing in the shade and enjoying the sweeping views of the Chianti hills, particularly at sunset. The rectangular swimming pool, which is non-heated, is located behind the villa on lower terracing and is reached by descending a few steps near the pergola. Lined in grey PVC, it measures 3 x 9 metres with a depth ranging from 1.40 to 1.60 metres, and features 3 steps for easy water access along with a chlorine purification system. The sunbathing area surrounding the pool combines stone paving and lawn, and is furnished with sunbeds and umbrellas. Dry stone walls and a thick screen of vines provide natural enclosure on either side, enhancing the sense of privacy. A cold-water outdoor shower is also available. The pool is accessible from the last Saturday in April to the first Saturday in October. Please note that the property photographs were taken in spring, so the appearance of flowering plants and garden grass may differ at the time of your arrival.
Unit Layout
Villa delle Upupe is configured across 2 floors that follow the natural slope of the terrain, connected by both internal and external staircases, and can comfortably accommodate up to 8 guests across 4 bedrooms and 4 bathrooms. The main entrance is located on the ground floor, which houses 2 double bedrooms and 1 twin bedroom, each with its own private bathroom. Of these 3 bathrooms, 2 are fitted with a shower and 1 features both a bathtub and a shower. Descending to the lower floor, you are welcomed into an elegant living room complete with an ornamental fireplace, alongside a dining room, both of which face the back garden. From the dining room, a few steps lead down to the fully equipped kitchen and to a room that serves as both a pantry and laundry area. The lower floor is completed by a 4th bedroom featuring a double divisible bed, an ensuite bathroom with shower, and a separate toilet. Both floors benefit from direct outside access, a distinctive architectural feature resulting from the property's adaptation to the sloping terrain, with the lower floor rooms opening directly onto the private garden.
Amenities Included
Villa delle Upupe is equipped with a comprehensive range of amenities to ensure a comfortable and convenient stay. The kitchen and laundry facilities are well appointed, including a dishwasher and a washing machine, making longer stays particularly practical. The villa operates an underfloor refrigeration and heating system, ensuring a pleasant indoor climate throughout the seasons, with heating available as required. For entertainment, the property is equipped with Satellite TV, allowing you to enjoy a wide selection of channels during your downtime. Pets are welcome at the villa, making it an ideal choice for guests travelling with their animal companions.
Other Information
Villa delle Upupe has a separate entrance and is situated approximately 50 metres from the owners' villa, from which it is screened by hedges to ensure maximum privacy for guests. The property has been subjected to a technical inspection prior to the beginning of the season to verify the consistency of the description, the condition of all listed accessories, and their operational and maintenance status, guaranteeing quality, cleanliness, and comfort. The Emma Villas Concierge Team is available to assist with any emergencies or further information required during your stay, and all relevant contact numbers are provided with the booking documents. Guests travelling with pets should be aware that a maximum of 1 animal is permitted, of small to medium size with a maximum weight of 10 kg. Acceptance of animals must be previously authorised by the owner, who requires advance communication of the number of animals, their size, and breed. Please be aware that the access road to the property includes 1.2 km of unpaved road, and low-clearance vehicles are not recommended.
Distances and Attractions
Villa delle Upupe is located approximately 2 km from the historic borgo of Castellina in Chianti, where you can find local shops, restaurants, and services. The estate's own winery, open for tastings and the sale of wine and extra virgin olive oil, is also approximately 2 km from the farmhouse, offering a unique opportunity to discover the exceptional products of the Castellare di Castellina estate. The property is conveniently close to the scenic Chiantigiana road, a panoramic route connecting Siena to Florence that serves as an ideal starting point for day trips to the celebrated localities of Radda, Gaiole, Greve, and Panzano, each rich in art treasures, historic churches, and Renaissance villas set on scenic hillsides. The entire surrounding region of Chianti Classico is internationally renowned for its picture-postcard landscapes and the excellence of its wines, making the villa an exceptional base from which to explore one of Italy's most beloved and storied territories.
Costs & Services
Included services
- Utilities: electricity, water, and gas for cooking purposes are included in the rental price
- Weekly linen change included
- Initial and final cleaning included
- Zer0Dep Guarantee: no security deposit is required on balance or on arrival; EuropAssistance coverage is included for accidental damage to the property during your stay, up to a maximum of €1,500.00 and subject to the limitations provided
Extra costs
- Tourism tax: €2.00 per person per day for the first 7 days (children under 14 years of age are exempt)
- Mandatory extra cleaning in case of animals: €50.00 per animal per week or part of a week
On request
- Extra cleaning: €22.00 per hour per person employed
- Extra linen change: €15.00 per person
- Heating from November to April: €12.00 per day Villa delle Upupe 8, Emma Villas
Castellare in Poggio 10
Villa rental with A/C, WIFI, private pool, TV, patio, pets allowed, close to Greve In Chianti
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10
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5
-
4
-
450 m2
Description
Property Summary
Castellare in Poggio is a captivating stone farmhouse vacation rental nestled in the heart of Chianti Classico, just 2 km from Castellina in Chianti, Italy. Set within the prestigious Castellare di Castellina estate, renowned for its premium Chianti Classico wines and olive oil, this remarkable property seamlessly blends traditional Tuscan architecture with contemporary comforts. Surrounded by olive groves, vineyards, and gently rolling hills, the villa commands breathtaking panoramic views of the Tuscan countryside that are truly unforgettable. The property comprises a main house and a separate single-story annex, offering generous space and privacy for families or groups alike. Guests benefit from a well-appointed yard enveloped in lush Mediterranean vegetation, creating an atmosphere of serene natural beauty. Connectivity is ensured through Internet WiFi access throughout the property, while a dedicated parking area shaded by cypress trees accommodates up to 5 vehicles, providing effortless convenience from the moment of arrival.
Outdoors
The outdoor spaces at Castellare in Poggio are a true celebration of the Tuscan landscape. The lush garden surrounding the property is planted with lavender, rosemary, jasmine, and cypress trees, creating a fragrant and visually stunning environment across multiple levels connected by charming stone paths and steps. A pergola adjacent to the living room offers a beautifully shaded alfresco dining area, perfect for long summer meals in the open air. At the lower level of the garden, to the rear of the main house, the oval-shaped non-heated swimming pool serves as a peaceful and inviting retreat. The pool measures 10 x 5 metres, with a depth ranging from 1.4 metres to 2.5 metres, and features chlorine filtration, a stone diving board, and a metal ladder for easy access. The surrounding pool terrace is paved with porphyry stone and equipped with sunbeds, as well as a pergola furnished with a stone table and bench, ideal for relaxing in the shade. External lighting ensures the pool area remains atmospheric and usable into the evening. The pool is open from the last Saturday of April to the first Saturday of October. Please note that photographs of the property were taken in spring, and therefore the flowering of plants and the colour of the garden grass may differ from what you observe upon arrival.
Unit Layout
Castellare in Poggio accommodates a maximum of 10 guests across 5 bedrooms and 4 bathrooms, distributed between the main house and the annex. The main house spans 3 floors, each thoughtfully arranged to provide comfort and functionality. On the first floor, the main entrance opens into a welcoming living room, followed by a fully equipped kitchen featuring French windows with direct access to the outside, a dining room, and a study complete with a piano. A bathroom with shower completes this level. On the second floor, guests will find a double bedroom and a twin bedroom that share a bathroom with shower, as well as a further double bedroom with a queen-size bed and a private ensuite bathroom with a bathtub. The ground floor houses a billiard room with a television and direct access to the garden, along with the laundry room, which benefits from its own independent entrance. The single-story annex offers a comfortable and self-contained living space comprising a living room with a kitchenette, a twin bedroom, a double bedroom, and a bathroom with shower, making it ideal for guests seeking a degree of additional privacy within the property.
Amenities Included
Castellare in Poggio is equipped with a comprehensive range of amenities designed to ensure a comfortable and enjoyable stay. Air conditioning is available in all bedrooms, providing a welcome respite during the warmer months of the Tuscan summer, while heating is also available for cooler periods. The laundry room on the ground floor of the main house is fitted with a washing machine, offering practical convenience for longer stays. In the kitchen, a dishwasher is available to make mealtimes effortless. Guests are also welcome to enjoy the private patio, an ideal space for outdoor relaxation and dining in complete privacy. Entertainment is well catered for, with Satellite TV available for guests to enjoy. The property is pet-friendly, welcoming animals subject to prior authorization from the owner, as detailed in the relevant house rules.
Other Information
Guests are kindly requested to seek prior authorization from the owner before bringing any animals to the property. Authorization requires advance communication of the number of animals, their size, and their breed. A maximum of 1 animal is permitted, and it must be small or medium-sized, weighing no more than 10 kg. Please be aware that all fireplaces and the wood-burning oven within the property are purely ornamental and are not available for use. The weekly rental rate includes utilities such as electricity, water, and gas for cooking purposes, as well as weekly linen service and both an initial and a final cleaning of the property. The rate also includes the Zer0Dep Guarantee, which means guests are not required to pay a security deposit either on balance or upon arrival. This guarantee provides EuropAssistance coverage in the event of accidental damage to the property during the stay, up to a maximum of 1,500.00 euros and subject to the limitations set out in the policy terms.
Distances and Attractions
Castellare in Poggio enjoys an exceptional location just 2 km from the charming hilltop town of Castellina in Chianti, where guests will find a selection of restaurants, wine bars, boutique shops, and local services. The property sits at the heart of the Chianti Classico wine region, one of Tuscany's most celebrated and scenic areas, offering guests the opportunity to explore world-class wineries, olive oil producers, and the iconic rolling landscapes that have made this corner of Italy famous across the globe.
Costs & Services
Included services
- Utilities (electricity, water, gas for cooking): included in the rental rate
- Weekly linen service: included in the rental rate
- Initial and final cleaning: included in the rental rate
- Zer0Dep Guarantee (EuropAssistance accidental damage coverage up to €1,500.00, subject to policy limitations): included in the rental rate
Extra costs
- Mandatory extra cleaning in case of animals: €50.00 per animal per week or part of a week (up to 1 animal, small or medium-sized, maximum 10 kg; prior owner authorization required)
- Tourism tax: where applicable, as required by local regulations
On request
- Extra cleaning: €22.00 per hour per cleaner
- Extra linen: €15.00 per person
- Heating: charged on consumption at current market prices
- Firewood: €15.00 per 100 kg Castellare in Poggio 10, Emma Villas
Pretty independent property with WIFI, private pool, pets allowed and panoramic view
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9
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5
-
3
-
200 m2
Description
Podere Sangiovese, Pool and View in Chianti is a beautiful vacation rental (200 sq m) with private pool and WiFi internet. The property can sleep up to nine guests comfortably in five bedrooms with three bathrooms. Podere Sangiovese, Pool and View in Chianti is located 6 km (4 mi) from Castellina In Chianti, Italy and only 27 km (17 mi) from Greve In Chianti in the tourist area "Siena And Surroundings".
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, stove and refrigerator, as well as, plenty of tableware and cutlery for up to nine people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 27 km (17 mi), Siena 28 km (17 mi), San Gimignano 30 km (18 mi), Florence 61 km (38 mi) and Montalcino 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 61 km (38 mi), Viareggio 154 km (96 mi), Forte Dei Marmi 161 km (100 mi), Rome 263 km (163 mi), Venice 307 km (191 mi) and Milan 357 km (222 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Podere Sangiovese, Pool and View in Chianti. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 15:00 - 18:30
Check-Out Time: 08:00 - 09:30
Pool Open: 1 May - 13 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 73 km (45 mi), Pisa (psa) 108 km (67 mi), Bologna (blq) 160 km (99 mi), Roma Ciampino (cia) 272 km (169 mi) and Roma Fiumicino (fco) 284 km (177 mi).
Podere Sangiovese, Pool and View in Chianti
Villa Pipirelli
Comfortable home with private pool, TV and terrace, near Siena
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10
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7
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7
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349 m2
Description
Property Summary
You will discover an exceptional holiday villa nestled in the heart of Sovicille, Italy, a magnificent 17th-century stone farmhouse completely immersed in the greenery of the beautiful Sienese mountain woods. This luxury property has been recently restored with extraordinary care and attention to detail, preserving many original features characteristic of Tuscan architecture both externally and internally. The surrounding area presents a protected rural landscape dominated by holm oaks, under which truffles and porcini mushrooms grow naturally, alongside olive groves and wildflowers. A scenic dirt road flanked by cypresses and oaks leads you to the villa, which comprises an independent main building and an outbuilding. The decor throughout is elegant yet eclectic, featuring exposed beamed ceilings, lime-washed walls in soft colors, and traditional terracotta floors, complemented by modern Italian touches in the fireplaces, bathrooms, and outdoor areas. The property offers parking facilities and presents the perfect retreat for those seeking authentic Tuscan luxury combined with contemporary comfort.
Outdoors
The outdoor spaces of this remarkable property are designed to maximize your enjoyment of the breathtaking Tuscan landscape. The centerpiece is a stunning infinity pool measuring 4.5 by 13 meters, set on a travertine terrace that blends seamlessly with the surrounding natural rock environment and offers spectacular views of the Montagnola Senese. A fountain of fresh water flows continuously into the pool, providing wonderfully clear water and a refreshing natural back massage. Steps from the living room lead down to the lower garden and park, where you will find beautifully landscaped grounds with pergolas and multiple terraces perfect for relaxing and dining alfresco. A covered terrace overlooks the courtyard, accessible from the upper landing, while another small furnished terrace off the dining room provides views of the woods and barn. The ground floor living room opens through French doors onto a Zen-style terrace overlooking the pool, ideal for enjoying evening cocktails and the last rays of sunlight. The barn features a paved terrace accessed through two large doors, perfect for outdoor dining. Additional outdoor amenities include a barbecue area, an external wood-burning bread and pizza oven, and a green space with pergola, all enhanced by security and ambient lighting throughout the grounds.
Unit Layout
The accommodation welcomes up to 10 guests across 7 bedrooms and 7 bathrooms, thoughtfully distributed between the main villa and the converted barn outbuilding. The main building is accessible via two separate entrances, with one leading to a lobby, wardrobe, and laundry room. To the right of this entrance, you will find a ground floor double bedroom with private bathroom with shower, specifically designed for wheelchair access. The second entrance opens directly into the expansive kitchen. Also on the ground floor, behind the dining room, is another double bedroom with an adjacent bathroom with shower. From the entrance, two ramps of ancient travertine stairs ascend to a landing that opens onto a covered terrace. On this upper level, to the right, you will find a double bedroom with private bathroom with shower, while to the left a large living room with fireplace connects to two additional double or twin bedrooms, each featuring ensuite bathrooms with both shower and bathtub. The adjoining barn has been transformed into a contemporary open-plan space accommodating 4 additional guests. On the upper level of the barn, you will discover two bedrooms, one double and one twin, each appointed with bath and shower. An open staircase descends from this loft level to the ground floor living area, which features a fireplace, dining room, and open-space kitchen.
Amenities Included
Your stay is enriched with comprehensive amenities designed for comfort and convenience throughout the property. The kitchen is fully equipped with all modern conveniences including a large oven, refrigerator with freezer, dishwasher, and microwave, with Tuscan walnut travertine work surfaces and a polished chestnut central island. Entertainment options include satellite television, a DVD player, and a stereo system for your enjoyment. The main villa features spectacular fireplaces built into natural rock, while the barn living area also includes a fireplace for atmospheric warmth. An external wood-burning bread and pizza oven alongside a barbecue facility provides exceptional outdoor cooking experiences. Laundry facilities are conveniently provided with a washing machine and dryer in the main building and an additional washing machine in the outbuilding. Modern conveniences extend to Wi-Fi connectivity, alarm system, and mosquito nets on all bedroom and bathroom windows. The property is fully wheelchair accessible with specially adapted facilities. Your private garden offers extensive grounds for relaxation and recreation, while the infinity pool features an integrated shower. Additional thoughtful touches include outdoor lighting for security and ambiance, telephone service, a welcoming case of six bottles of local wine, and a bottle of extra virgin olive oil upon arrival.
Other Information
Air conditioning is installed in all bedrooms in both the main house and barn, as well as in the upstairs lounge of the main villa, ensuring comfort throughout your stay. Maid service is provided each day for general cleaning and remaking of beds, with a full change of sheets and towels once a week, typically mid-week on Wednesday. Breakfast is included each morning as part of your stay. Gardener and grounds maintenance services ensure the property remains immaculately presented throughout your visit. An English-speaking concierge service is available on request to assist with information and arrangements. The property provides towels specifically for swimming pool use. A baby cot is available on request for families traveling with infants. The minimum stay requirement is 7 nights during high season and 5 nights during mid and low season. A tourist tax may be required upon arrival according to the regulations of the host municipality. Screens are fitted on all bedroom and bathroom windows for your comfort and protection from insects.
Distances and Attractions
The villa occupies a privileged position in the Montagnola Senese, surrounded by protected rural landscapes and beautiful woods characteristic of the Sienese mountain region. The property is situated within the municipality of Sovicille, offering easy access to the cultural and historical treasures of Tuscany while maintaining the tranquility and privacy of a secluded countryside location. The surrounding area is renowned for its truffle and porcini mushroom foraging opportunities, with holm oak forests providing the perfect natural habitat. The olive groves and wildflower meadows that characterize the landscape offer wonderful opportunities for walking and exploring the authentic Tuscan countryside.
Costs & Services
Included services
- Breakfast each morning
- Maid service each day for general cleaning and remaking of beds
- Full change of sheets and towels once a week
- Gardener and grounds maintenance
- Case of six bottles of local wine
- Bottle of extra virgin olive oil
- Towels for swimming pool
- Cleaning service
- Wi-Fi
On request
- Daily cleaning: €25.00 per hour
- Catering services
- Babysitting services
- Guide services
- Driver services
- Bike rental: €20.00 per day or €125.00 per week
- Chef for lunches and dinners
- Buffet breakfast arrangements
- Theme nights such as barbecue and pizza evenings
- Typical Tuscan dinner
- Additional housekeeping
- Cook and catering
- English speaking concierge service
- Baby cot
- Telephone service Villa Pipirelli
Pretty independent villa rental with WIFI, A/C, pool, balcony, pets allowed and panoramic view
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4
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2
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1
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105 m2
Description
Conveniently located 7 km (4 mi) from Castellina In Chianti, Italy in the tourist area "Siena And Surroundings" and only 28 km (17 mi) from Greve In Chianti. Property Civico108 Vacation Home, Pool, Castellina in Chian is a beautiful property (105 sq m) that includes air conditioning and WiFi internet. The property can accommodate up to four people comfortably in two bedrooms with one bathroom.
What to Expect
When you arrive you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. For your enjoyment you will find a pool where you can relax while enjoying a nice cold beverage after a busy day of visiting museums. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 28 km (17 mi), Siena 29 km (18 mi), San Gimignano 31 km (19 mi), Florence 62 km (38 mi) and Montalcino 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 62 km (38 mi), Viareggio 155 km (96 mi), Forte Dei Marmi 162 km (101 mi), Rome 264 km (164 mi), Venice 308 km (191 mi) and Milan 358 km (222 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Civico108 Vacation Home, Pool, Castellina in Chian. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 15:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 74 km (46 mi), Pisa (psa) 109 km (68 mi), Bologna (blq) 160 km (100 mi), Roma Ciampino (cia) 273 km (169 mi) and Roma Fiumicino (fco) 285 km (177 mi).
The hamlet Le Miniere di Liliano, private and authentic, is home to only a few families and guarantees tranquility, with access to a shared swimming pool and tennis court for residents. Civico108 Vacation Home, Pool, Castellina in Chian
Casa Fioraie
Independent House with private pool, WIFI, A/C, TV, patio, panoramic view, close to Greve In Chianti
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6
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2
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2
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110 m2
Description
Holiday home in a strategic position in Castellina in Chianti.
Casa Fioraie is the ideal place to spend a relaxing and fun holiday.
The house offers two bedrooms (with air conditioning) as well as a large outdoor area, perfect for organizing barbecues and enjoying the wonderful panoramic view of the surrounding hills. In the garden there is a beautiful private pool that allows guests to relax and cool off in the summer season.
The property, thanks to its spacious interiors and its large exteriors, guarantees a pleasure and safe stay. All the areas, including the swimming pool, are carefully sanitized and sterilized for the health and tranquility of guests.
The Chianti Classico area in which Casa Fioraie is located is one of the most renowned places in Italy and in the world for its characteristic villages, food and wine culture, splendid cities of art and breathtaking scenery.
You reach the house through a gravel road of about 500 meters in good condition but not suitable for particularly sporty vehicles.
At guests' disposal: 2 air-conditioned bedrooms, double sofa bed for 2 people, possibility of accommodating 4/6 people, panoramic private pool (10 x 4.5 meters, maximum depth: 1.60 meters, minimum depth: 1, 20 meters), barbecue, outdoor area equipped with sofas and table with chairs for outdoor dining, Wi-Fi internet connection.
Distances: a Restaurant / Bar is located at 850 meters from the house, Castellina in Chianti (all kinds of shops) at 6 km, Poggibonsi at 14 km, Radda at 18 km, San Gimignano at 25 km, Siena at 30 km, Florence at 50 km, Pienza at 85 km, Montepulciano at 95 km, Cortona at 105 km, the Tuscan coast (Cecina or Castiglioncello) is at 100 km away.
Please carefully check if there are any extra costs to be paid on site! Casa Fioraie