Vacation Rentals with Air Conditioning in Gaggiano, Italy
Results 121 - 140 of 298
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Description
Property Summary
Nestled in the rolling Tuscan countryside of Siena, Italy, the charming detached house "L'Oliviera" offers a truly peaceful and sun-drenched retreat for those seeking an authentic holiday rental experience. Positioned in a quiet, elevated setting just 5 km from the historic centre of Siena, this beautiful property is surrounded by trees, open fields, and sits only 100 metres from the edge of a forest, creating a natural and serene atmosphere. The house benefits from complimentary Wi-Fi throughout, allowing guests to stay connected while enjoying the tranquillity of the Tuscan landscape. Private parking is conveniently available directly at the property, ensuring effortless arrivals and departures for those exploring the surrounding region by car.
Outdoors
The outdoor spaces of "L'Oliviera" are a true highlight of the property, offering guests a private and immersive connection with the natural Tuscan environment. The grounds feature a well-maintained lawn alongside a wildlife garden, thoughtfully designed to blend harmoniously with the surrounding countryside and its native flora and fauna. The property is enveloped by trees and open fields, providing a sense of seclusion and privacy that makes it an ideal setting for relaxing outdoors, breathing in the fresh country air, and enjoying the unspoiled beauty of the Sienese hills.
Other Information
Guests should be aware that heating at "L'Oliviera" is available and billed on-site, applicable during the period from 10 April to 31 October. Baby equipment is provided and included at no additional charge, making the property a practical and welcoming choice for families travelling with young children. The owner resides on the same property, ensuring a reassuring presence and the opportunity for personalised local assistance throughout the stay. Guests should also be aware that the owner keeps a dog on the premises. As the property is situated in a rural setting, the use of a car is strongly recommended in order to fully enjoy the surrounding area and access nearby services with ease.
Distances and Attractions
"L'Oliviera" enjoys a convenient location with easy access to a wide range of everyday amenities and cultural landmarks. A grocery store is located just 3 km away, while a shopping centre can be reached within 4 km, and a restaurant is a short 2 km drive from the property. Public transport is readily accessible, with a bus stop situated only 100 metres from the house, and the railway station "Siena" reachable within 6 km. For those wishing to explore the wider Tuscan region, the thermal baths of "Rapolano Terme" are approximately 35 km away, offering a wonderful opportunity for relaxation and wellness. The medieval village of Monteriggioni lies just 16 km from the property, while the iconic hilltop town of San Gimignano is 36 km away. The breathtaking landscape of the Crete Senesi can be explored within 30 km, and the celebrated wine town of Montalcino is situated 45 km from the house. The Renaissance gem of Pienza is approximately 50 km away, and Montepulciano, renowned for its Vino Nobile, can be reached within 65 km, making "L'Oliviera" an exceptional base from which to discover the very best of Tuscany. L'Oliviera
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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
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Amazing independent holiday home with WIFI, private pool, A/C 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 beautiful property (200 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with five bathrooms.
Your Experience
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany. 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 eight people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the perfect setting to enjoy food, family and the beautiful Tuscan weather.
What's 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: 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.
Villa del Mangia, 5Panoramic Pool and Chef Service
Wonderful independent holiday home with private pool, A/C, WIFI, terrace and panoramic view
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Description
Villa del Mangia is a villa located just a few kilometers from Siena.
The villa consists of a main building spread over two floors and an external annex, a former stone barn, which serves as the guesthouse. The total area of the property is 400 sqm. The entire complex was fully renovated in 2024, with incredible attention to detail and the use of high-quality materials, skillfully combining the charm of Tuscan tradition with modern comforts, furnishings, and top-tier materials, offering a luxurious and sophisticated environment. The villa, meticulously curated in every detail, reflects the refined taste of the owner and an emphasis on rare, high-quality materials.
The outdoor spaces have been designed with great care, creating a harmonious connection between the villa and the surrounding natural environment. The garden features lush terraced areas, olive trees, and spacious open areas, ideal for hosting large families or groups of friends seeking a relaxing and convivial vacation.
The interiors, enhanced by marbles that provide luminosity and contemporary design, are equipped with a floor heating and cooling system to ensure maximum comfort. At the same time, original elements such as the ceilings and exposed beams preserve the villa's historic charm, offering a perfect balance between the old and the new.
The annexed barn is equally welcoming, with a breathtaking view of Siena: every window in this building frames a picture-perfect scene.
The spacious indoor and outdoor areas provide the opportunity to enjoy moments together without sacrificing tranquility or the possibility of retreating to more intimate spaces. Ideal for large families or groups wanting to spend a pleasant vacation together while maintaining privacy, this villa allows you to fully enjoy the Sienese countryside, while being just a short drive from some of Tuscany's most famous destinations, such as Siena, San Gimignano, and Florence. Villa del Mangia, 5Panoramic Pool and Chef Service
Book your vacation for the period from 01 June 2026 to 26 June 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 01 July 2026 to 31 July 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 09 September 2026 to 19 September 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 13 October 2026 to 31 October 2026 and save 10% (minimum 3 nights).
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 | |||||
|---|---|---|---|---|---|
| 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
Montelucci Chianti Agrivilla
Wonderful private vacation rental with private pool, A/C, WIFI, TV, patio and panoramic view
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Description
Montelucci Chianti Agrivilla is located 560 m (1795 ft) from Montegrossi, Italy and only 30 km (18 mi) from Greve In Chianti in the tourist area "Chianti". Montelucci Chianti Agrivilla is a nice stone building (400 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to 14 people comfortably in seven bedrooms with six bathrooms.
The Experience
Upon arrival at Montelucci Chianti Agrivilla you’ll find a beautiful clean well-maintained property with views of the mountains and the hills perfect 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Outdoors you will also find a patio and barbecue grill. 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 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 nice Tuscan weather.
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: Greve In Chianti 30 km (18 mi), Siena 37 km (23 mi), San Gimignano 50 km (31 mi), Arezzo 54 km (34 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 77 km (48 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 171 km (106 mi), Rome 258 km (160 mi), Milan 368 km (229 mi) and Naples 449 km (279 mi).
Additional Information
Check-In Time: 17:00 - 22:00
Check-Out Time: 07:00 - 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) 82 km (51 mi), Pisa (psa) 144 km (90 mi), Bologna (blq) 171 km (106 mi), Roma Ciampino (cia) 267 km (166 mi) and Roma Fiumicino (fco) 280 km (174 mi).
More Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while learning the techniques vital to master Tuscan cuisine. For more details and the extra 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 arrange 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 supplemental costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be arranged by the owner. Ask for more details about the extra 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 supplemental cost and how to arrange this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service after arriving.
Montelucci Chianti Agrivilla
Casa Scopeti
Private Accommodation with A/C, WIFI, private pool, hot tub, TV, panoramic view, near Florence
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Description
Nice independent villa situated in panoramic location in the heart of the Tuscan country-side. This property has been restored preserving its original architectural features and turned into a comfortable villa with private swimming-pool offering nice interiors furnished in a typical country style.
The access to the property is via an unpaved but well-maintained road.
Distances: the small village of Falciani with food shops 2 km away, San Casciano with all kinds of shops 5 km, Florence 10 km, Greve in Chianti with a charming central square and nice restaurants 20 km, Siena 60 km away.
At guests’ disposal: nice garden furnished with sun-beds and sun umbrellas, private swimming-pool (6 x 12 m – maximum depth 1,4 m – open from 01/04 to 31/10), heated outdoor Jacuzzi (7 seats), barbecue, veranda, playground for children. All of the bedrooms are provided with air-conditioning. Ironing facilities available. WI-FI internet connection available (free of charge for a usage of 15 hours per week - extra consuption to be paid on site at € 0,90 / per hour).
Parking within the grounds.
Extra services: maid service available by arrangement (€ 10,- / per hour to be paid on the spot). It is possible to arrange cooking classes and cooking service.
Small pets are allowed.
Please carefully check if there are any extra costs to be paid on site! Casa Scopeti
Book 15 days or less before the arrival date and receive a 25 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Cottage Monti Pet Friendly with Shared Pool
Pretty villa rental with pool, WIFI, A/C, TV, veranda and pets allowed, near San Gimignano
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Description
Conveniently located 1 km (4699 ft) from La Corsina, Italy in the tourist area "San Gimignano And Surroundings" and only 24 km (15 mi) from San Gimignano. Cottage Monti Pet Friendly With Shared Pool is a nice vacation rental (70 sq m) with WiFi internet and air conditioning. The property can accommodate up to four people comfortably.
The cottage has a large private area with a private veranda equipped for outdoor dining. The property is very large and includes the manor house in front of which there is a swimming pool shared with the owners who occasionally stay in the manor house.
Free parking on the property.
What to Expect
After arriving at Cottage Monti Pet Friendly With Shared Pool you’ll find a beautiful 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. Dining 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 vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
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 24 km (15 mi), Siena 41 km (26 mi), Greve In Chianti 49 km (30 mi), Florence 65 km (41 mi) and Montalcino 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 112 km (69 mi), Forte Dei Marmi 123 km (77 mi), Rome 276 km (171 mi), Venice 314 km (195 mi) and Milan 364 km (226 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Cottage Monti Pet Friendly With Shared Pool. 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: 1 May - 1 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) 78 km (48 mi), Pisa (psa) 84 km (52 mi), Bologna (blq) 167 km (104 mi), Genova (goa) 254 km (158 mi) and Roma Fiumicino (fco) 262 km (163 mi).
Special Services
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Cottage Monti Pet Friendly With Shared Pool
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 20% (minimum 7 nights).
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 25% (minimum 10 nights).
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 28% (minimum 14 nights).
Alice - Podere Ribatti - Casole D'Elsa, Toscana
Great apartment with WIFI, A/C, pool and terrace, near San Gimignano
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Description
Vacation rental Alice - Podere Ribatti - Casole D'elsa, Toscana is a nice property (100 sq m) that includes air conditioning and WiFi internet. The property can sleep up to two people comfortably in one bedroom with one bathroom. Conveniently located 3 km (2 mi) from Casole D'elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 22 km (14 mi) from San Gimignano.
What to Expect
When you arrive you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. For your enjoyment you will find a pool where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. There is a kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to two people.
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: San Gimignano 22 km (14 mi), Siena 38 km (23 mi), Greve In Chianti 56 km (35 mi), Florence 63 km (39 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 63 km (39 mi), Viareggio 155 km (96 mi), Forte Dei Marmi 165 km (102 mi), Rome 272 km (169 mi), Venice 310 km (193 mi) and Milan 358 km (222 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
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) 76 km (47 mi), Pisa (psa) 87 km (54 mi), Bologna (blq) 163 km (101 mi), Roma Ciampino (cia) 281 km (175 mi) and Roma Fiumicino (fco) 294 km (183 mi).
Alice - Podere Ribatti - Casole D'elsa, Toscana
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 15% (minimum 10 nights).
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 18% (minimum 14 nights).
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 20% (minimum 21 nights).
Chianti Hills Apartment, Pool, Ac
Fantastic flat with A/C, WIFI, TV, patio and panoramic view, near Florence
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Description
Chianti Hills Apartment, Pool, Ac is located 9 km (5 mi) from San Casciano In Val Di Pesa, Italy and only 16 km (10 mi) from Florence in the tourist area "Florence And Surroundings". Chianti Hills Apartment, Pool, Ac is a nice vacation rental (80 sq m) with air conditioning and WiFi internet. The property can accommodate up to five people comfortably.
The pool and garden are to be shared with the owner, who lives upstairs in the same property.
Your Experience
After arriving 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 peaceful holiday in Tuscany. For your enjoyment you will find a where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. 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 five people.
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: Florence 16 km (10 mi), Greve In Chianti 27 km (17 mi), San Gimignano 50 km (31 mi), Siena 68 km (42 mi) and Pisa 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 16 km (10 mi), Viareggio 99 km (62 mi), Forte Dei Marmi 111 km (69 mi), Rome 288 km (179 mi), Milan 313 km (194 mi) and Naples 478 km (297 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 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) 19 km (12 mi), Pisa (psa) 72 km (45 mi), Bologna (blq) 118 km (73 mi), Genova (goa) 242 km (150 mi) and Venezia (vce) 272 km (169 mi).
Chianti Hills Apartment, Pool, Ac
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Description
Property Summary
"Ambrogetta" is a charming 1800-built cottage located just 1 km from the center of San Casciano In Val Di Pesa, Italy, offering a peaceful and tranquil vacation rental experience with easy access to local amenities. The property boasts a lovely swimming pool (8 x 4 meters, 120 cm deep) available from May 1 to October 22, an outdoor shower, a vast 20,000 square meter garden with a lawn and trees, parking for two cars, and internet WiFi.
Outdoors
Guests can enjoy the property's expansive 20,000 square meter outdoor area, featuring a beautiful garden with a lawn and trees. While the garden is not fenced, it offers a serene and relaxing environment to unwind after exploring the surroundings. Additionally, the property provides a roofed parking area that can accommodate up to two vehicles.
Other Information
"Ambrogetta" offers convenient access to local transportation, with a bus stop located just 300 meters away, making it easy to explore the area even without a personal vehicle.
Distances and Attractions
The vacation rental's strategic location offers easy access to renowned attractions such as Florence, Siena, and San Gimignano, allowing guests to immerse themselves in the rich cultural and historical heritage of Italy while enjoying the comfort and tranquility of "Ambrogetta." Ambrogetta
Il Gabbro, Luxury Experience
Beautiful private holiday home with WIFI, private pool, A/C and TV
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Description
Il Gabbro, Luxury Experience is located 8 km (5 mi) from Casole D'elsa, Italy and only 31 km (20 mi) from San Gimignano in the tourist area "Central Tuscany". Il Gabbro, Luxury Experience is a lovely holiday home (450 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to ten guests comfortably in five bedrooms with six bathrooms.
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 ideal for a relaxing 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 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 ten people.
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: San Gimignano 31 km (20 mi), Siena 46 km (29 mi), Greve In Chianti 57 km (35 mi), Florence 72 km (45 mi) and Montalcino 82 km (51 mi).
Some other major tourist destinations you should consider visiting are: Florence 72 km (45 mi), Viareggio 121 km (75 mi), Forte Dei Marmi 133 km (82 mi), Rome 281 km (174 mi), Venice 319 km (198 mi) and Milan 369 km (229 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 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) 85 km (53 mi), Pisa (psa) 93 km (58 mi), Bologna (blq) 171 km (106 mi), Roma Fiumicino (fco) 262 km (163 mi) and Genova (goa) 263 km (163 mi).
Il Gabbro, Luxury Experience
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Description
Property Summary
Situated in San Casciano In Val Di Pesa, Italy, the "Sole" is a renovated, three-story cozy farmhouse surrounded by trees and vineyards. The property offers a terraced garden with wildlife, an above-ground swimming pool (3 x 8 m, seasonal availability: 31.May - 30.Sep), and outdoor amenities like a shower, terrace, garden furniture, and barbecue. Additionally, you can enjoy Internet Wifi, parking, and a yard during your vacation rental stay.
Outdoors
The property boasts a fenced, 600 m2 private area with a terraced garden featuring a wildlife section and trees. Take advantage of the outdoor shower, terrace, garden furniture, and barbecue facilities. The swimming pool (above ground, 3 x 8 m) is available seasonally from May 31 to September 30, with maintenance provided by the owner/gardener.
Other Information
Convenient services include linen and towel changes (supplemental charges apply), cook upon request (extra cost), and a pre-arrival grocery service. The property can be accessed via an 800m long bumpy, narrow motor access road. On-site parking is available for up to 4 cars. Local sale of farm products is available nearby.
Distances and Attractions
The property is located 2.5 km from the center of San Casciano and offers proximity to various amenities and attractions. Within 2 km, you'll find shops, groceries, supermarkets, restaurants, bakeries, bicycle rentals, and a bus stop. The Florence Santa Maria Novella railway station is 22 km away, while the sandy beach is 90 km from the property. Nearby attractions include Florence (22 km), San Gimignano (40 km), Siena (60 km), and Pisa (74 km). For leisure activities, a golf course (18 holes) is 21 km away, tennis courts are 4 km away, and walking paths start 100 m from the house. An indoor swimming pool is also available 4 km from the property. Sole
Il Casale
Stunning private villa with WIFI, private pool, TV, patio, pets allowed and panoramic view
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Description
Property Summary
Immerse yourself in the rustic charm of "Il Casale," a cozy vacation rental nestled in the picturesque countryside of Tuscany. This charming cottage boasts a private garden with a meadow, providing the perfect setting to relax and unwind. Enjoy a refreshing dip in the seasonal above-ground swimming pool (8 x 4 m) while taking in the breathtaking views of the surrounding landscape. Stay connected with internet wifi access, and take advantage of the provided garden furniture, barbecue facilities, and private parking on the premises.
Outdoors
Embrace the natural beauty that surrounds "Il Casale." Explore the private garden with its lush meadow, offering a tranquil oasis for you to escape the hustle and bustle of everyday life. Indulge in al fresco dining or simply bask in the warm Tuscan sun while enjoying the stunning countryside vistas.
Other Information
For your convenience, "Il Casale" is located just 2.5 km from the center of Badia a Passignano and 5 km from the center of Montefiridolfi. Please note that the property is accessed via a 2 km long bumpy motor access through an unmade road. Additionally, the owner utilizes some rooms within the house. Experience the authentic flavors of Tuscany by purchasing local farm products available for sale on-site.
Distances and Attractions
While "Il Casale" offers a peaceful retreat, it is conveniently situated just 30 km from the vibrant center of Florence and 90 km from the sea. Explore the surrounding area and discover nearby shops, supermarkets, and the Poggibonsi railway station (20 km), providing easy access to other attractions in the region. Immerse yourself in the natural beauty of San Casciano In Val Di Pesa, Italy, and create lasting memories during your vacation rental stay. Il Casale
Agriturismo Agresto Apartments and Cottage, Pool,
Comfortable apartment with pool, WIFI, A/C, TV and panoramic view, close to San Gimignano
- 4
- 15
- 6
- 4
| Accommodation | |||
|---|---|---|---|
| Noce Cottage with Pool, Casole D'Elsa | 2 | 1 | 1 |
Description
Agriturismo Agresto Apartments And Cottage, Pool, is located in Casole D'elsa, Italy and only 24 km (15 mi) from San Gimignano in the tourist area "San Gimignano And Surroundings". Property Agriturismo Agresto Apartments And Cottage, Pool, is a nice property that includes shared pool, WiFi internet and air conditioning. The apartment has been divided into a total of four independent units. The property can accommodate up to 15 guests comfortably.
The Experience
After arriving at Agriturismo Agresto Apartments And Cottage, Pool, you’ll find a lovely clean well-maintained property with views of the hills perfect for a peaceful vacation 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. Each apartment has its own private living area with a kitchen with plenty of utensils, tableware and cutlery, a bedroom and bathroom. Many people traveling with friends prefer a multi-unit property where they can spend time together in the common areas, like the pool or garden, but still have their own private living quarters.
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: San Gimignano 24 km (15 mi), Siena 39 km (25 mi), Greve In Chianti 53 km (33 mi), Florence 65 km (40 mi) and Montalcino 76 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (40 mi), Viareggio 114 km (71 mi), Forte Dei Marmi 126 km (78 mi), Rome 274 km (170 mi), Milan 359 km (223 mi) and Naples 465 km (289 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 20 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) 78 km (48 mi), Pisa (psa) 87 km (54 mi), Bologna (blq) 164 km (102 mi), Genova (goa) 257 km (159 mi) and Roma Fiumicino (fco) 261 km (162 mi).
Agriturismo Agresto Apartments And Cottage, Pool,
Villa Agnola
Unique private villa rental with WIFI, private pool, A/C, TV and patio, close to Greve In Chianti
- 11
- 6
- 6
Description
Villa Agnola is a beautiful stone building (400 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to 11 guests comfortably in six bedrooms with six bathrooms. Conveniently located in the centre of San Casciano In Val Di Pesa, Italy in the tourist area "Florence And Surroundings" and only 20 km (12 mi) from Greve In Chianti.
The villa is on one single level on the ground floor. The 1st floor of the villa is closed and cannot be used by guests.
Your Experience
After arriving 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 peaceful 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. There is a kitchen including microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 11 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 vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 20 km (12 mi), Florence 21 km (13 mi), San Gimignano 41 km (25 mi), Siena 61 km (38 mi) and Pisa 75 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 21 km (13 mi), Viareggio 115 km (71 mi), Forte Dei Marmi 122 km (76 mi), Rome 290 km (180 mi), Venice 271 km (169 mi) and Milan 313 km (194 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 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) 34 km (21 mi), Pisa (psa) 76 km (48 mi), Bologna (blq) 120 km (75 mi), Genova (goa) 255 km (158 mi) and Venezia (vce) 274 km (170 mi).
Villa D'agnola
Mattei Villa
Wonderful private property with A/C, hot tub, private pool, WIFI, TV, close to Greve In Chianti
- 12
- 6
- 6
Description
# Property Summary
Casa Mattei is a dramatically located villa in San Casciano In Val Di Pesa, situated in the heart of Tuscany's Chianti region with expansive views over olive groves, vineyards, woods and country estates. This authentic property welcomes 10 guests plus 4 additional guests and offers a stunning swimming pool with Jacuzzi feature. The spacious and private country house stands just 2 kilometers from Mercatale Val di Pesa and 18 kilometers from Florence, Italy. You will find the location ideal with its private and tranquil hillside position, perfectly positioned for exploring the region. The well-appointed villa has been authentically restored and is surrounded by olive groves, making it perfect for 5 to 6 couples or extended families. Internet Wifi connectivity ensures you stay connected throughout your stay, while convenient parking facilities are provided on the property. The building dates back approximately one thousand years to the Medieval period and was totally restored in 2006, having originally served as a small monastery before evolving into a country house some centuries later. As a member of the Experience Villas Collection, Casa Mattei offers its guests a fun and very Italian experience through a Pizza Cooking Class with a professional Pizzaiolo.
Outdoors
The fenced property extends across 2 hectares and includes the main house of 530 square meters, a swimming pool measuring 15 by 7.50 meters, and a dependence of 40 square meters. The fresh water pool with integrated Jacuzzi is open from May through September and you should note that the Jacuzzi is not a hot tub. The pool area is furnished with sunbeds, tables and chairs with umbrellas for your comfort. Adjacent to the pool you will discover a changing room with a bathroom featuring a shower and a well equipped fitness room. The lawn is beautifully bordered with rose bushes and olive trees, creating a picturesque setting. A stone patio houses a barbecue and provides shaded space for al fresco dining at a long table accommodating 12 people with comfortable chairs. Steps from the patio lead you down to the pool area, allowing easy access between the outdoor living spaces.
Other Information
Access to Casa Mattei is via a typically rough dirt road extending 1200 meters through vineyards and olive groves.
Distances and Attractions
You will appreciate the exceptional location of Casa Mattei, positioned just 15 minutes south from Florence with easy access to the charming Chianti hill towns. The property sits 50 minutes from Siena and 1 hour from Lucca, allowing you to explore some of Tuscany's most celebrated destinations. The nearest village of Mercatale Val di Pesa is only 2 kilometers away, while the cultural treasures of Florence are accessible at 18 kilometers from your accommodation. Mattei Villa
Book your vacation for the period from 01 March 2026 to 30 June 2026 and save 10% (minimum 7 nights). Offer valid until 30 June 2026.
Medieval Castle Living: Vineyards, Swimming Pool &
Fantastic holiday home with private pool, WIFI, A/C, balcony and panoramic view, close to Siena
- 12
- 6
- 6
Description
Vacation rental Medieval Castle Living: Vineyards, Swimming Pool & is a beautiful stone building (800 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to 12 guests comfortably in six bedrooms with six bathrooms. Conveniently located 4 km (2 mi) from Sovicille, Italy in the tourist area "Siena And Surroundings" and only 14 km (8 mi) from Siena.
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).
The Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills perfect for a peaceful holiday 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 sightseeing. For your pleasure, on the grounds there is a barbecue grill and playground. Dining 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, toaster, 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 balcony is the perfect setting to enjoy food, family and the lovely Tuscan weather.
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 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).
Additional 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 pleasant way to spend time with friends and family while discovering the techniques required 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 holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will organize the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the additional costs.
Meals - If you'd like to have meals provided during your visit, either half-board or full-board is available. If you prefer only breakfast be provided, that can be scheduled as well. Inquire about the additional costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the individual 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 &
Book now and save 10%. Offer valid until 10 May 2026 and for a minimum stay of 2 nights.
Siena 631
Pretty multi-unit accommodation with WIFI, pool, A/C, terrace, pets allowed and panoramic view
- 3
- 8
- 4
- 5
| Accommodation | |||
|---|---|---|---|
| Il Boschetto 631.2 | 4 | 2 | 2 |
Description
Property Summary
Montecagnano is a stunning agricultural estate located in Sovicille, Italy, offering four detached houses surrounded by trees and four apartments. This vacation rental boasts a beautiful terraced garden spanning 3 hectares, adorned with plants, trees, and an orchard. The estate features a fenced swimming pool measuring 15 x 7 meters with a depth of 100 - 250 cm, available seasonally from May 15th to October 15th, along with an outdoor shower. It provides amenities such as Internet Wifi, Parking, and an Installment Plan. Montecagnano offers a secluded escape while being conveniently located near local attractions.
Outdoors
Montecagnano's standout feature is its breathtaking terraced garden, spanning 3 hectares and fenced for privacy. The garden is adorned with a variety of plants, trees, and an orchard, creating a serene and natural atmosphere. The estate boasts a stunning swimming pool, fenced for safety, measuring 15 x 7 meters with a depth ranging from 100 to 250 cm. The pool is available seasonally from May 15th to October 15th, with operating hours from 9:00 AM to 7:00 PM. Guests can also enjoy an outdoor shower, enhancing the alfresco experience.
Other Information
Montecagnano offers a unique rural retreat while providing modern amenities for convenience. The estate features Internet Wifi, allowing you to stay connected during your stay. Additionally, the property offers the option of an Installment Plan for your accommodation. Guests can purchase farm products from the local sale, immersing themselves in the authentic agricultural experience. It's important to note that the owner of the estate resides on the premises and has a dog.
Distances and Attractions
Montecagnano is conveniently situated just 1.1 km from the center of Montecagnano and 12 km away from the charming city of Siena, known for its rich history and cultural attractions. Florence, another renowned destination, is just 67 km away from the estate. For daily essentials, a supermarket is located 8 km from the property. Nature enthusiasts can enjoy the nearby sandy beach of Marina di Cecina, situated 92 km away, offering a perfect day trip destination. Siena 631
Special Offer for Il Boschetto 631.2
Villa Melinda
Independent House with private pool, WIFI, A/C, TV, terrace, pets allowed, close to San Gimignano
- 6
- 3
- 3
Description
Beautiful villa located in the countryside between Siena and Florence, renovated in 2015 maintaining and enhancing the rustic style and at the same time equipping it with all comforts to ensure a relaxing and welcoming environment. The house is arranged over three floors and has an attractive design with a taste of modern combined with some antique furniture. The property also has a small fenced garden of 1,000 sq m. equipped with pool for exclusive use of the guests (11m. x 5m. prof. 150cm.), there is also a nice loggia equipped for outdoor dining with barbecue.
Possibility to arrange chef service and cooking classes (upon request and to be paid on the spot); possibility of massages by professionals (to be arranged directly on the spot).
Free Wi-Fi internet. Air conditioning throughout. Parking near the property (30 meters). Access to the house with 150m. of unpaved road. The property is located at 8km. from the center of "Certaldo", at 19km. from "San Gimignano", at 20km. from the golf course, at 55km. from Siena and 59km. from Florence. Villa Della Meletta
Book 42 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 7 nights minimum and can not be combined with any other special offers.
