Vacation Rentals with Air Conditioning in Siena, Italy
Results 41 - 60 of 269
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In high demand!
Description
Property Summary
'Terrazza sul Chianti' is a large, modern two-story house renovated in 2025, situated in Castellina In Chianti, Italy. It offers amenities such as a yard, internet WiFi, and parking on the premises, ideal for your vacation rental. The property is part of a residential complex with two houses, providing a secluded and elevated position on a slope with a west-facing view.
Outdoors
The property boasts a natural state, fenced outdoor area shared among the residences, allowing you to enjoy the surroundings. Additionally, it offers convenient parking facilities right at the house.
Other Information
Nearby conveniences include shops, groceries, supermarkets, restaurants, bakeries, and a bus stop just 30 meters away. The "Castellina Scalo" railway station is 7 km away, and there's an outdoor swimming pool within 1 km distance. Baby equipment is included, making it family-friendly. Please note that part of the house is closed and unoccupied, and the owner resides on the same property. The main road is in close proximity.
Distances and Attractions
The property is 1.2 km from the center of Castellina in Chianti. Nearby attractions include Siena (20 km), Greve in Chianti (20 km), Radda in Chianti (12 km), Gaiole in Chianti (22 km), San Gimignano (27 km), and Firenze (44 km). The sandy beach "Cecina Mare" is 95 km away, offering a perfect opportunity to combine your holiday rental with a beach getaway. Terrazza sul Chianti
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Description
Property Summary
Welcome to "Casa Chiara," a modern two-story vacation rental built in 2009 and conveniently located just 300 meters from the center of the charming town of Castellina In Chianti, Italy. This property boasts a private, terraced yard spanning 40 square meters, providing a peaceful outdoor space to relax and unwind. Enjoy the convenience of on-site parking, including a single garage, as well as seamless internet Wi-Fi connectivity throughout your stay.
Outdoors
Embrace the tranquility of "Casa Chiara's" private, terraced yard spanning 40 square meters, offering a serene outdoor oasis for your enjoyment. While the yard is not fenced, its sunny and quiet location ensures a peaceful retreat during your holiday rental in Castellina In Chianti. Explore the charming town center, just a 3-minute walk away, and discover the nearby walking paths that stretch for 500 meters, inviting you to immerse yourself in the picturesque surroundings.
Other Information
Castellina In Chianti offers a plethora of amenities and attractions within close proximity to "Casa Chiara." A shop, grocery store, and supermarket are all conveniently located within walking distance, ensuring you have everything you need for a comfortable stay. The pedestrian zone, restaurant, and bar are also just 300 meters away, providing ample opportunities to experience the local cuisine and lively atmosphere. For those seeking recreational activities, an outdoor swimming pool is located just 3 kilometers away, while an indoor pool is 12 kilometers from the property.
Distances and Attractions
Strategically located in the heart of Tuscany, "Casa Chiara" offers easy access to some of the region's most celebrated destinations. Radda in Chianti is just 12 kilometers away, while Greve in Chianti is a 20-kilometer drive. The historic cities of Siena and San Gimignano are within reach at 26 and 34 kilometers, respectively. For those seeking cultural immersion, Florence and Pisa are within a day trip's distance, at 50 and 100 kilometers away. Closer to home, the thermal baths at "Rapolano Terme" offer a rejuvenating experience just 50 kilometers from your holiday rental, and golf enthusiasts can enjoy an 18-hole course a mere 35 kilometers away. Casa Chiara
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Stunning private vacation home with A/C, private pool, WIFI and TV
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Description
La Dimora del Chianti Dimora: Stunning Tuscan Vill is located 5 km (3 mi) from Rietine, Italy and only 27 km (17 mi) from Siena in the tourist area "Siena And Surroundings". La Dimora del Chianti Dimora: Stunning Tuscan Vill is a lovely property (200 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to eight guests comfortably in four bedrooms with five bathrooms.
What to Expect
After arriving you’ll find a nice clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping 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. 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 eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Visit the Area
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 27 km (17 mi), Greve In Chianti 33 km (21 mi), Arezzo 52 km (32 mi), San Gimignano 54 km (33 mi) and Montalcino 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 159 km (99 mi), Forte Dei Marmi 167 km (103 mi), Rome 240 km (149 mi), Venice 316 km (196 mi) and Milan 359 km (223 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 19 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) 78 km (49 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 165 km (102 mi), Roma Ciampino (cia) 249 km (155 mi) and Roma Fiumicino (fco) 261 km (162 mi).
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Book now and save 10%. Offer valid until 20 April 2026 and for a minimum stay of 5 nights.
Castellina in Chianti 647
Wonderful multi-unit villa with pool, WIFI, A/C, TV, patio and panoramic view
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Someone just enquired about this property!
| Accommodation | |||||
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| Cerretino Tettoia 647.1 | 4 | 2 | 1 | ||
| Cerretino Vigna 647.2 | 4 | 2 | 2 | ||
| Cerretino Oliveto 647.3 | 6 | 3 | 3 | ||
| All 3 Accommodations | 14 | 7 | 6 |
Description
Property Summary
Cerretino is a cozy, rustic country house surrounded by fields and vineyards in Castellina In Chianti, Italy. It offers amenities including a Swimming Pool, Yard, Internet Wifi, Parking, and an Installment Plan. The property comprises three houses in a residence, situated just 1 km from the center of Castellina in Chianti, in a sunny position, 200 m from the forest edge, and amidst the countryside.
Outdoors
The property boasts a shared natural state area, a swimming pool (6 x 12 m, depth 100 - 180 cm, seasonal availability: 15th May - 15th October), an outdoor shower, patio, terrace, and garden furniture. The pool maintenance is handled by the owner or gardener. Access to the house is via a 300 m long, very bumpy, and narrow motor road, with parking available at the house.
Other Information
Nearby amenities include a shop, grocery, supermarket, restaurant, bar, bakery, and pedestrian zone within 1 km. The bus stop "SR 222" is 200 m away, while the railway station "Castellina Scalo" is 11 km away. The sandy beach "Cecina Mare" is 88 km away, and the thermal baths "Rapolano Terme" are 50 km from the property. Walking paths are accessible from the house at a distance of 200 m. Baby equipment is included in the holiday rental.
Distances and Attractions
Nearby attractions include Panzano in Chianti (13 km), Greve in Chianti (20 km), Gaiole in Chianti (20 km), Siena (26 km), San Gimignano (42 km), and Firenze (50 km). Castellina in Chianti 647
Special Offer for Cerretino Tettoia 647.1
Apartment:
Cerretino Vigna 647.2
Last-Minute Offer for Cerretino Tettoia 647.1
Other apartments with last-minute offers:
Cerretino Vigna 647.2
Cerretino Oliveto 647.3
Castellina in Chianti 618
Stunning multi-unit villa with A/C, WIFI, pool, TV, patio, pets allowed and panoramic view
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| Accommodation | |||||
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| Cignanbianco - Alba e Tramonto 618.1 | 9 | 5 | 3 | ||
| Cignanbianco - Alba 618.2 | 3 | 2 | 1 | ||
| Cignanbianco - Tramonto 618.3 | 6 | 3 | 2 | ||
| All 3 Accommodations | 18 | 10 | 6 |
Description
Property Summary
Country House "Cignanbianco" is a picturesque property nestled amidst fields and vineyards in Castellina In Chianti, Italy. Offering a serene and tranquil environment, it comprises three houses and seven apartments, making it an ideal vacation rental for families and friends seeking a rejuvenating getaway. The property boasts an extensive 30-hectare area adorned with lush plants, trees, and natural gardens, creating a harmonious blend of nature and comfort. Guests can indulge in the luxurious amenities provided, including a stunning 12 x 6-meter swimming pool, available seasonally from May 2nd to October 3rd, meticulously maintained by the owner and gardener. Additionally, a yard, internet Wifi, parking facilities, and an installment plan option are available for your convenience.
Outdoors
Country House "Cignanbianco" offers an idyllic outdoor experience for its guests. The property features a stunning 12 x 6-meter swimming pool, available seasonally from May 2nd to October 3rd, meticulously maintained by the owner and gardener. Surrounded by lush greenery and a tranquil atmosphere, the pool area beckons you to relax and soak up the Tuscan sun while enjoying a refreshing swim. Embrace the true essence of outdoor living by indulging in a delightful barbecue session while basking in the beauty of the natural gardens and picturesque landscapes.
Other Information
Country House "Cignanbianco" provides a range of conveniences to ensure a comfortable and hassle-free holiday rental experience. Shared facilities include a washing machine and ample parking spaces on the premises. The owner, who resides on the same property, offers the opportunity to purchase locally sourced farm products, allowing you to savor the authentic flavors of the region. Additionally, baby equipment is included in the rental, catering to families traveling with young children. Groups of teenagers are welcome upon request, making it an ideal destination for multi-generational gatherings.
Distances and Attractions
Strategically located in Castellina In Chianti, Italy, Country House "Cignanbianco" provides easy access to a wealth of local attractions and amenities. The charming town center of Castellina in Chianti is just 5 km away, while Castellina Scalo is a mere 6 km distance. Siena, a renowned tourist destination renowned for its rich history and cultural heritage, is conveniently situated 27 km from the property. Nearby attractions for day trips include the picturesque towns of Moneriggioni (10 km), San Gimignano (29 km), San Galgano (50 km), Volterra (52 km), and Montalcino (65 km). Additionally, the property is in close proximity to bicycle rentals, bus stops, and a railway station, ensuring seamless mobility. For those seeking a beach getaway, Cecina Mare is located 83 km away, while an indoor swimming pool is just 15 km from the property. Castellina in Chianti 618
Special Offer for Cignanbianco - Tramonto 618.3
Last-Minute Offer for Cignanbianco - Alba e Tramonto 618.1
Other apartments with last-minute offers:
Cignanbianco - Alba 618.2
Cignanbianco - Tramonto 618.3
Castellina in Chianti 625
Cosy apartment with WIFI, A/C, pool, TV, patio, pets allowed and panoramic view
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| Accommodation | |||
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| La Foresta 625.3 | 6 | 3 | 2 |
Description
Property Summary
Agriturismo "La Foresta" is a charming vacation rental situated in the picturesque region of Castellina In Chianti, Italy, surrounded by fields and vineyards. The property comprises 4 apartments in the residence, located 10 km from the centre of Castellina in Chianti and 12 km from the centre of Siena, offering a quiet, sunny position in the countryside. You will enjoy access to a fenced swimming pool measuring 6 x 14 m with seasonal availability from 01.May. - 15.Oct., maintained by the owner/gardener. The property features a spacious yard with plants and trees, meadow areas, and outdoor amenities including an outdoor shower, patio, terrace, and garden furniture. Internet Wifi connectivity ensures you remain connected during your stay. Roofed parking is conveniently available at the house, and the property is accessed via a 2 km long bumpy motor access road. An installment plan may be available for your booking convenience. The residence includes a reception area and a washing machine for shared use among guests. Baby equipment is included, and you may purchase farm products locally. Please note that all houses/apartments are individually designed and furnished.
Outdoors
The outdoor spaces at La Foresta provide excellent opportunities for relaxation and recreation in the Tuscan countryside. For shared use, you will find an extensive property featuring plants and trees throughout the meadow areas. The fenced swimming pool, measuring 6 x 14 m, offers refreshing enjoyment with seasonal availability from 01.May. - 15.Oct., with regular pool maintenance performed by the owner/gardener. An outdoor shower is conveniently located near the pool area. The terrace and patio spaces are equipped with garden furniture, creating ideal settings for outdoor dining and relaxation. A barbecue is available for preparing meals while enjoying the surrounding views of fields and vineyards that characterize this quiet, sunny position in the countryside.
Other Information
Access to the property requires traveling along a 2 km long bumpy motor access, and a car is recommended for your stay. Roofed parking is provided at the house for your convenience. Within the residence, you will find a reception area and a washing machine available for shared use. Baby equipment is included with your accommodation. The property offers local sale of farm products, allowing you to experience authentic Tuscan agricultural offerings. Please note that all houses/apartments within the residence are individually designed and furnished, ensuring each unit has its own unique character and style.
Distances and Attractions
The location provides convenient access to essential services and fascinating nearby attractions in the Chianti region. A shop, grocery, and supermarket are all located 6 km from the property, while a restaurant can be found just 2 km away. The bus stop "Via Chiantigiana" is situated 2 km from La Foresta, and the railway station "Siena" is 12 km away. Among the nearby attractions, you will find Siena at 12 km, Greve in Chianti at 20 km, San Gimignano at 25 km, and Firenze at 65 km, offering numerous opportunities for cultural exploration and sightseeing throughout your stay in Castellina In Chianti, Italy. Castellina in Chianti 625
Special Offer for La Foresta 625.3
Last-Minute Offer for La Foresta 625.3
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In high demand!
Description
Property Summary
Nestled in the serene Tuscan countryside of Castellina in Chianti, Italy, the charming apartment house "Fiore di Mandorlo" offers an exceptional holiday rental experience in a secluded and sun-drenched setting, just 4 km from the centre of Castellina in Chianti. This beautifully renovated historical residence carries the character and warmth of its origins while providing all the comforts expected of a refined country retreat. The property sits within a natural state estate, offering guests the exclusive use of a private garden and yard where the tranquillity of the Tuscan landscape can be fully appreciated. Convenient private parking is available directly at the house, ensuring effortless arrivals and departures. Wifi internet connectivity is provided, allowing guests to remain connected throughout their stay while enjoying the peaceful rural surroundings.
Outdoors
The outdoor spaces of "Fiore di Mandorlo" invite guests to immerse themselves in the beauty of the Chianti countryside. The private garden, maintained in its natural state, provides a genuine and unspoilt environment ideal for relaxing and enjoying the abundant Tuscan sunshine. The surrounding grounds offer ample space for outdoor leisure, with the property's secluded position ensuring complete privacy and a deep sense of calm. For those wishing to swim, an outdoor swimming pool is accessible just 3 km from the property.
Other Information
Baby equipment is included as part of the property offering, making "Fiore di Mandorlo" a thoughtful choice for families travelling with young children. A car is recommended in order to make the most of the property's countryside location and to reach the surrounding towns, services, and attractions with ease.
Distances and Attractions
The property is ideally positioned to explore the rich cultural and gastronomic heritage of Tuscany. The centre of Castellina in Chianti is located just 4 km away, where guests will find a selection of local shops and a supermarket, both reachable within the same distance. The bus stop "Chiantigiana" is situated 2 km from the property. The magnificent city of Siena, renowned for its medieval architecture and the famous Piazza del Campo, is approximately 25 km away, while Florence, one of the world's most celebrated art and cultural destinations, can be reached in approximately 45 km. This privileged location places guests within easy reach of the finest vineyards, hilltop villages, and landscapes that define the heart of the Chianti region. Fiore di Mandorlo
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Someone else is looking at this property right now!
Description
Conveniently located in Gaiole In Chianti, Italy in the tourist area "Siena And Surroundings" and only 29 km (18 mi) from Siena. Property Villa Di Gaiole is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to 12 people comfortably in six bedrooms with four bathrooms.
The Experience
When you arrive at Villa Di Gaiole you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, shopping 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. There is a kitchen including microwave 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 garden where you can enjoy the weather while dining outdoors.
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: Siena 29 km (18 mi), Greve In Chianti 30 km (18 mi), San Gimignano 50 km (31 mi), Arezzo 58 km (36 mi) and Florence 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 62 km (38 mi), Viareggio 156 km (97 mi), Forte Dei Marmi 163 km (101 mi), Rome 251 km (156 mi), Venice 312 km (194 mi) and Milan 354 km (220 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 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) 75 km (46 mi), Pisa (psa) 121 km (75 mi), Bologna (blq) 161 km (100 mi), Roma Ciampino (cia) 260 km (162 mi) and Roma Fiumicino (fco) 273 km (169 mi).
Villa Radda
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Description
Villa Pianvecchio is located 2 km (1 mi) from Radda In Chianti, Italy and only 22 km (14 mi) from Greve In Chianti in the tourist area "Siena And Surroundings". Villa Pianvecchio is a beautiful holiday rental with WiFi internet, air conditioning and private pool. The property can sleep up to 12 people comfortably in six bedrooms with six bathrooms. There is a golf course nearby if you'd like to get in a round or two while on vacation.
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. Dining 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 vacation. The kitchen includes coffee machine, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
Places Nearby
Most people enjoy visiting nearby 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 22 km (14 mi), Siena 37 km (23 mi), San Gimignano 42 km (26 mi), Florence 54 km (33 mi) and Arezzo 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 54 km (33 mi), Viareggio 145 km (90 mi), Forte Dei Marmi 155 km (96 mi), Rome 258 km (160 mi), Venice 305 km (189 mi) and Milan 348 km (216 mi).
Additional Information
Pool: it can be heated and the water is not treated with chlorine, but salt.
Pool Open: 1 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) 69 km (43 mi), Pisa (psa) 113 km (70 mi), Bologna (blq) 153 km (95 mi), Roma Ciampino (cia) 267 km (166 mi) and Roma Fiumicino (fco) 280 km (174 mi).
More Services
Maid Service - If you'd like maid service during your stay that can be scheduled by the owner. Ask for more details about the supplemental cost.
Wine cellar: on the lower floor of the Villa, there is also a Wine cellar with a selection of wines for sale. The cellar remains locked unless you wish to buy wine and you ask to the housekeeper. Villa Pianvecchio
Villa Castiglioni
Private House with sauna, WIFI, private pool, hot tub, A/C, TV, patio, close to Greve In Chianti
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Description
Property Villa Castiglioni is a beautiful property that includes WiFi internet, air conditioning and private pool. The property can accommodate up to 11 people comfortably in five bedrooms with seven bathrooms. Conveniently located 4 km (2 mi) from Radda In Chianti, Italy in the tourist area "Siena And Surroundings" and only 23 km (14 mi) from Greve In Chianti.
The road to get to the property is not asphalted.
Your Experience
Upon arrival at Villa Castiglioni you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful 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 unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outside are a playground, patio and barbecue grill.
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: Greve In Chianti 23 km (14 mi), Siena 30 km (19 mi), San Gimignano 43 km (27 mi), Florence 55 km (34 mi) and Arezzo 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 55 km (34 mi), Viareggio 149 km (93 mi), Forte Dei Marmi 157 km (97 mi), Rome 253 km (157 mi), Venice 306 km (190 mi) and Milan 347 km (216 mi).
Additional Information
Pool Open: 1 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) 68 km (42 mi), Pisa (psa) 130 km (81 mi), Bologna (blq) 155 km (96 mi), Roma Ciampino (cia) 262 km (163 mi) and Roma Fiumicino (fco) 274 km (170 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques required to master Tuscan cuisine. The owner can schedule 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 mouth-watering Tuscan meals when you return home. For more details and the additional cost, please contact us.
Maid Service - If you'd like maid service during your stay that can be arranged by the owner. Ask for more details about the additional cost.
Additional Information
- Fire wood is provided by the owner.
- The guests may not use the laundry. This is organized by the house keeper.
- The cleaning of the outside pool is done daily.
- 5 hours a day cleaning and laundry (except Sunday) are included in the rental price.
- The overseer is available 5 hours per day. He can also cook for the guests and remain longer if necessary. This service is available on request and on payment.
- The Electricity has to be paid if the usage results to be over 600 kw. Villa Castiglioni
Villa del Poggio
Unique private house with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
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Description
Property Summary
Villa del Poggio is a rustic single-family house located in the peaceful countryside just 2 km from the charming village of Radda in Chianti, Italy. It offers a beautiful, well-kept garden spanning 5,000 m2, complete with a Swimming Pool, Yard, Internet Wifi, and Parking for up to three cars. With three bedrooms, two bathrooms, and a fully equipped kitchen, this vacation rental provides a comfortable stay amidst the stunning Tuscan surroundings.
Outdoors
Guests can enjoy a variety of outdoor activities, including swimming in the 12 x 5 m pool (available seasonally from May to October), sunbathing on the lawn, relaxing in the orchard or arbour, playing table tennis, and cycling with the provided bicycles. Guided bike and mountain bike tours are available upon request. The terrace and garden furniture offer a delightful setting for al fresco dining and relaxation.
Other Information
The owner lives on the same property and is available for any questions or requests during your stay. Cooking courses can be booked on request, providing an opportunity to immerse yourself in the local culinary traditions.
Distances and Attractions
Villa del Poggio is ideally situated for exploring the beautiful villages of Radda in Chianti and Castellina in Chianti, both located just a short drive away. Its prime location allows guests to experience the charm and beauty of the Tuscan countryside while enjoying the comforts of a well-appointed vacation rental. Villa del Poggio
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Description
Property Summary
Montefienali is a historical holiday village located 15 km from Gaiole in Chianti, Italy, nestled in the countryside at an elevation of 600 meters above sea level. This renovated 13th-century property offers 25 apartments within a hamlet of 25 houses. Guests can enjoy a natural state property spanning 3 hectares with plants, trees, and a seasonal swimming pool (10 x 15 m) available from May 15 to September 30, with pool opening hours from 9:00 AM to 8:00 PM. The property boasts amenities such as a children's pool, outdoor shower, patio, terrace, garden furniture, and a children's playground with a slide, swing, and sandbox. Laundry facilities (shared) are available on-site. While the property is accessible via a 2 km bumpy motor access road, it offers parking on the premises and is within proximity to shops, groceries, supermarkets, restaurants, bars, and bicycle rentals, making it an ideal vacation rental for families seeking a peaceful retreat in the Tuscan countryside.
Outdoors
Immerse yourself in the natural beauty of Montefienali, surrounded by trees on a fenced 3-hectare property. Soak up the sun by the seasonal swimming pool (10 x 15 m), available from May 15 to September 30, with designated pool opening hours from 9:00 AM to 8:00 PM. Children can make a splash in the dedicated children's pool or enjoy the outdoor playground with a slide, swing, and sandbox. Relax on the patio or terrace, surrounded by lush gardens and equipped with comfortable garden furniture. Outdoor showers are also available for your convenience.
Other Information
Montefienali offers convenient on-site amenities, including a shared washing machine for laundry needs. While the property is situated in a secluded location, it is easily accessible via a 2 km bumpy motor access road, with parking available on the premises. A 50-meter footpath leads from the parking area to the accommodations. The property caters to families, with baby equipment provided. Please note that groups of teenagers are accepted upon request only.
Distances and Attractions
Nestled in the Tuscan countryside, Montefienali is conveniently located near various attractions and amenities. The charming town of Gaiole in Chianti is just 15 km away, offering shops, groceries, and a supermarket. Restaurants and bars can be found within a 3 km radius, while bicycle rentals are available 15 km from the property. Explore the rich history and culture of nearby cities such as Siena (36 km), Arezzo (44 km), and Florence (66 km), all within a reasonable driving distance from your vacation rental. Il Cinghiale
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| Accommodation | |||||
|---|---|---|---|---|---|
| San Regolo 915.1 | 2 | 1 | 1 | ||
| San Regolo 915.2 | 4 | 2 | 2 | ||
| All 2 Accommodations | 6 | 3 | 3 |
Description
Property Summary
Villa San Regolo is a stunning vacation rental located in the picturesque hamlet of San Regolo, just 10 km from the charming town of Gaiole In Chianti, Italy. This resort boasts 6 houses, offering guests a serene and peaceful escape. The property is equipped with a range of amenities, including a swimming pool, internet WiFi, parking facilities, an EV charging station, and the option for an installment plan.
Outdoors
Immerse yourself in the beauty of the Tuscan countryside at Villa San Regolo. The resort features a shared swimming pool (15 x 6 m, with a depth ranging from 120 to 220 cm) available seasonally from May 1st to October 25th. Guests can also enjoy a children's pool, an outdoor shower, and a beautifully maintained garden with furniture, tended to by the owner/gardener.
Other Information
Villa San Regolo offers a range of additional services and facilities to enhance your stay. The complex features a reception area, and guests can indulge in relaxing massages (at an extra cost). Central heating is available, along with laundry facilities, including a shared washing machine. Heating costs are payable on-site (from March 29th to October 31st) and is available from November 1st to March 28th. Bicycles (6) are available for rent (extra charge), and a cook can be arranged upon request (additional cost). Parking is provided on the premises, and an e-charging station is available for electric vehicles.
Distances and Attractions
Villa San Regolo is conveniently located near several attractions and points of interest. The Castello di Brolio is just 2 km away, while Castelnuovo Berardenga is 13 km from the resort. The historic city of Siena is a 20 km drive, and Castellina in Chianti is 27 km away. Other nearby destinations include Greve in Chianti (35 km), Monteriggioni (35 km), and Monte San Savino (39 km). For those seeking a beach getaway, the sandy shores of Castiglione della Pescaia are 115 km from the resort, and the thermal baths of Rapolano Terme are just 26 km away. Gaiole in Chianti 915
Gaiole in Chianti 649
Pretty multi-unit villa with WIFI, private pool, A/C, TV, terrace, pets allowed and panoramic view
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| Accommodation | |||||
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| Montechioccioli 649.1 | 6 | 2 | 1 | ||
| Montechioccioli 649.2 | 6 | 2 | 1 | ||
| All 2 Accommodations | 12 | 4 | 2 |
Description
Property Summary
The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the charming hamlet of Rietine, just 4 km from the center of Gaiole In Chianti, Italy. This property features three apartments available for rent, making it an ideal choice for families or groups of friends seeking to experience the beauty of Tuscany. Montechioccioli boasts a range of amenities, including a Swimming Pool, Yard, Internet Wifi, Parking, and an Installment Plan.
Outdoors
Montechioccioli is a true countryside gem with a terraced garden spanning 1,000 m2, adorned with a variety of plants and trees. It offers a serene setting for guests to relax and take in the stunning views of the Tuscan countryside. The property boasts a seasonal swimming pool, measuring 12 x 6 m with a depth of 170 cm, available from May 2nd to October 3rd. The pool area features a shower/WC and a terrace with a barbecue, perfect for alfresco dining and enjoying the warm Italian evenings.
Other Information
The property provides additional conveniences, such as a washing machine for shared use and parking on the premises. It is worth noting that the owner resides on the same property. Montechioccioli offers a truly unforgettable vacation rental experience in the heart of Tuscany.
Distances and Attractions
Montechioccioli is strategically located just 12 km from the center of Radda in Chianti and 40 km from the historic city of Siena, making it an ideal base for exploring the region's many attractions. Nearby, guests can discover the charming town of Gaiole in Chianti, known for its rich cultural heritage and picturesque surroundings. Gaiole in Chianti 649
Special Offer for Montechioccioli 649.1
Apartment:
Montechioccioli 649.2
Last-Minute Offer for Montechioccioli 649.1
Other apartments with last-minute offers:
Montechioccioli 649.2
Villa Campiglia
Independent Villa with private pool, WIFI, A/C, TV, patio, panoramic view, near San Gimignano
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Description
Villa Campiglia is a lovely holiday rental (110 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to six people comfortably in three bedrooms with three bathrooms. Conveniently located 8 km (5 mi) from Colle Di Val D'elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 17 km (11 mi) from San Gimignano.
The owners, friendly and at the same time discrete, live in an annex in the basement and are available to help, if necessary.
The Experience
After arriving you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a relaxing vacation in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of shopping. For your pleasure, on the grounds there is 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 six people. If you prefer to dine 'al fresco', there is a fully furnished balcony where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting nearby 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: San Gimignano 17 km (11 mi), Siena 34 km (21 mi), Greve In Chianti 51 km (32 mi), Florence 58 km (36 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 58 km (36 mi), Viareggio 114 km (71 mi), Forte Dei Marmi 125 km (78 mi), Rome 273 km (169 mi), Venice 309 km (192 mi) and Milan 352 km (219 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 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) 73 km (45 mi), Pisa (psa) 86 km (54 mi), Bologna (blq) 158 km (98 mi), Genova (goa) 259 km (161 mi) and Roma Ciampino (cia) 282 km (175 mi).
Villa Campiglia
Villa L'Elsa Beautiful Country Home with View
Private Accommodation with sauna, A/C, private pool, hot tub, WIFI, terrace, close to San Gimignano
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Description
Villa L'elsa Beautiful Country Home With View is a beautiful holiday rental (350 sq m) with air conditioning, hot tub and private pool. The property can sleep up to 14 guests comfortably in seven bedrooms with six bathrooms. Villa L'elsa Beautiful Country Home With View is located 4 km (3 mi) from Colle Di Val D’elsa, Italy and only 10 km (6 mi) from San Gimignano in the tourist area "San Gimignano And Surroundings".
The Experience
Upon arrival you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid vacation in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a barbecue grill and hot tub. Sharing a meal 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 vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the lovely Tuscan weather.
Visit the Area
Most people enjoy visiting nearby 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: San Gimignano 10 km (6 mi), Siena 32 km (20 mi), Greve In Chianti 40 km (25 mi), Florence 52 km (32 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 52 km (32 mi), Viareggio 146 km (91 mi), Forte Dei Marmi 153 km (95 mi), Rome 266 km (165 mi), Venice 303 km (188 mi) and Milan 346 km (215 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 March - 1 March (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) 65 km (40 mi), Pisa (psa) 92 km (57 mi), Bologna (blq) 151 km (94 mi), Roma Ciampino (cia) 275 km (171 mi) and Genova (goa) 284 km (176 mi).
Special Services
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Villa L'elsa Beautiful Country Home With View. Ask for more details, including the additional cost and how to organize this service.
Villa L'elsa Beautiful Country Home With View
Book 4 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 5 nights minimum and can not be combined with any other special offers.
Anilde, Holiday Home with Pool, Wifi, Tuscany
Beautiful private property with private pool, WIFI, A/C, TV and pets allowed, close to San Gimignano
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Description
Conveniently located 7 km (4 mi) from Colle Di Val D’elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 23 km (14 mi) from San Gimignano. Anilde, Holiday Home with Pool, Wifi, Tuscany is a beautiful stone building (150 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to eight people comfortably in four bedrooms with two bathrooms.
Your Experience
Upon arrival at Anilde, Holiday Home with Pool, Wifi, Tuscany you’ll find a lovely clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of visiting museums. Sharing a meal with friends and family is a big 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, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people.
What's Nearby?
Most people enjoy visiting nearby 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: San Gimignano 23 km (14 mi), Siena 28 km (17 mi), Greve In Chianti 50 km (31 mi), Florence 57 km (36 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 57 km (36 mi), Viareggio 152 km (94 mi), Forte Dei Marmi 159 km (99 mi), Rome 267 km (166 mi), Milan 352 km (219 mi) and Naples 457 km (284 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Anilde, Holiday Home with Pool, Wifi, Tuscany. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 21 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) 70 km (44 mi), Pisa (psa) 105 km (65 mi), Bologna (blq) 157 km (98 mi), Roma Ciampino (cia) 276 km (171 mi) and Roma Fiumicino (fco) 288 km (179 mi).
Anilde, Holiday Home with Pool, Wifi, Tuscany
Book your vacation for the period from 28 April 2026 to 16 May 2026 and save 20% (minimum 3 nights).
Book your vacation for the period from 16 May 2026 to 27 June 2026 and save 15% (minimum 3 nights).
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Description
Terrazza e Libreria is located 4 km (3 mi) from Monte Benichi, Italy and only 32 km (20 mi) from Siena in the tourist area "Siena And Surroundings". Terrazza e Libreria is a lovely stone building with pool, air conditioning and WiFi internet. The apartment has been divided into a total of two private apartments. The property can accommodate up to six guests comfortably in three bedrooms with three bathrooms.
Your Experience
Upon arrival you’ll find a lovely clean well-maintained property perfect for a splendid vacation in Tuscany. For your pleasure you will find a pool where you can relax while enjoying a nice cold beverage after a busy day of shopping. A lot of people traveling with friends prefer a multi-unit holiday rental where they can spend time together in the common areas, like the pool or garden, but still have their own private living quarters with bedroom and bathroom. In addition, each apartment has its own kitchen with plenty of utensils, tableware and cutlery.
Visit the Area
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 32 km (20 mi), Arezzo 38 km (24 mi), Montepulciano 49 km (30 mi), Greve In Chianti 60 km (37 mi) and Montalcino 61 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 84 km (52 mi), Viareggio 171 km (106 mi), Forte Dei Marmi 178 km (111 mi), Rome 225 km (140 mi), Venice 327 km (203 mi) and Milan 371 km (230 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:00 - 10:00
Pool Open: 15 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) 92 km (57 mi), Pisa (psa) 152 km (94 mi), Bologna (blq) 176 km (109 mi), Roma Ciampino (cia) 234 km (146 mi) and Roma Fiumicino (fco) 247 km (153 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while discovering the secrets needed to prepare delicious 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 delicious meal using local produce? The chef will organize 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 additional costs.
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner after arriving 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. Ask for more details about the additional cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Terrazza e Libreria. Inquire for more details, including the supplemental cost and how to schedule this service.
Baby Sitting - A babysitter can be scheduled at Terrazza e Libreria. If you're traveling with kids and would like some alone time, speak to the owner directly about this option after arriving.
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.
Terrazza e Libreria
Portanuova Home, Colle Val D'Elsa
Beautiful apartment with A/C, WIFI and TV, close to San Gimignano
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Description
Portanuova Home, Colle Val D'elsa is located in Colle Di Val D'elsa, Italy and only 18 km (11 mi) from San Gimignano in the tourist area "San Gimignano And Surroundings". Property Portanuova Home, Colle Val D'elsa is a lovely property (160 sq m) that includes air conditioning and WiFi internet. The property can accommodate up to five people comfortably in two bedrooms with two bathrooms.
The Experience
When you arrive you’ll find a nice clean well-maintained property with views of the city ideal for a splendid vacation 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 for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to five people.
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: San Gimignano 18 km (11 mi), Siena 31 km (19 mi), Greve In Chianti 40 km (25 mi), Florence 53 km (33 mi) and Montalcino 67 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 53 km (33 mi), Viareggio 147 km (91 mi), Forte Dei Marmi 154 km (96 mi), Rome 265 km (165 mi), Venice 303 km (188 mi) and Milan 344 km (214 mi).
Additional Information
Check-In Time: 15:00 - 18:00
Check-Out Time: 09:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 65 km (41 mi), Pisa (psa) 102 km (64 mi), Bologna (blq) 152 km (94 mi), Roma Ciampino (cia) 274 km (170 mi) and Genova (goa) 285 km (177 mi).
Portanuova Home, Colle Val D'elsa
Book your vacation for the period from 13 June 2025 to 06 January 2027 and save 10% (minimum 7 nights).
Book your vacation for the period from 13 June 2025 to 06 January 2027 and save 15% (minimum 14 nights).
Agriturismo la Pieve
Superb multi-unit villa with WIFI, pool, A/C, TV, patio and panoramic view, near San Gimignano
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| Accommodation | |||||
|---|---|---|---|---|---|
| Suite del Duca | 2 | 1 | 1 | ||
| Ermitage | 2 | 1 | 1 | ||
| Appartamento dei Cavalieri | 2 | 1 | 1 | ||
| All 3 Accommodations | 6 | 3 | 3 |
Description
Holiday rental Agriturismo La Pieve is a beautiful property that includes shared pool, WiFi internet and air conditioning. The villa / farmhouse / home has been divided into a total of three private apartments. The property can sleep up to six guests comfortably in three bedrooms with three bathrooms. Conveniently located 8 km (5 mi) from Colle Di Val D’elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 17 km (10 mi) from San Gimignano. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
Your Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property perfect for a splendid holiday in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a barbecue grill and patio. This holiday rental is a multi-unit property which is ideal for a group of friends or acquaintances traveling together that want to have private living and sleeping quarters while sharing the common areas, such as the pool or garden, with the group. Each apartment is equipped with its own fully-equipped kitchen for meal preparation.
What's 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: San Gimignano 17 km (10 mi), Siena 37 km (23 mi), Greve In Chianti 51 km (32 mi), Florence 57 km (36 mi) and Montalcino 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 57 km (36 mi), Viareggio 153 km (95 mi), Forte Dei Marmi 160 km (99 mi), Rome 271 km (169 mi), Venice 309 km (192 mi) and Milan 352 km (219 mi).
Additional Information
Check-In Time: 14:30 - 21:00
Check-Out Time: 06:00 - 10:00
Pool Open: 1 April - 30 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) 91 km (57 mi), Bologna (blq) 154 km (96 mi), Roma Ciampino (cia) 280 km (174 mi) and Genova (goa) 293 km (182 mi).
Agriturismo La Pieve
Special Offer for Ermitage
Book your vacation for the period from 01 April 2026 to 15 June 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 01 October 2026 to 03 November 2026 and save 10% (minimum 2 nights).
