Luxury Villas with Pool in Gaiole in Chianti, Italy
Results 61 - 67 of 67
Villa San Giovanni
Independent Property with WIFI, private pool, A/C, TV, patio, panoramic view, near Montalcino
- 10
- 5
- 6
Someone just enquired about this property!
Description
Vacation rental Villa San Giovanni is a lovely property (320 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to ten people comfortably in five bedrooms with six bathrooms. Villa San Giovanni is located 1 km (4171 ft) from San Giovanni D'asso, Italy and only 19 km (12 mi) from Montalcino in the tourist area "Orcia Valley".
Your Experience
Upon arrival you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful vacation in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. Outdoors you will also find 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 ten people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
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: Montalcino 19 km (12 mi), Montepulciano 33 km (21 mi), Siena 44 km (27 mi), Cortona 50 km (31 mi) and Arezzo 55 km (34 mi).
Some other major tourist destinations you should consider visiting are: Florence 111 km (69 mi), Viareggio 221 km (137 mi), Forte Dei Marmi 228 km (142 mi), Rome 216 km (134 mi), Milan 421 km (262 mi) and Naples 407 km (253 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 140 km (87 mi), Pisa (psa) 159 km (99 mi), Roma Ciampino (cia) 225 km (140 mi), Bologna (blq) 226 km (141 mi) and Roma Fiumicino (fco) 238 km (148 mi).
Additional Services
Tours The owner can organize custom truffle hunting tours followed by truffle, wine and olive oil tasting for your group. To learn about the tours available, inquire prior to booking to ensure availability. The cost will vary depending on the specific tour and number of people.
Tasting The owner can organize custom truffle, wine and olive oil tasting for your group. To learn more, inquire prior to booking. The cost will vary depending on the number of people.
Painting lessons The owner can organize custom painting lessons with a talented artist for your group. To learn more, inquire prior to booking. The cost will vary depending on the number of people.
Cooking Lessons - Learn from a local chef the techniques vital 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 learning the secrets needed to prepare sumptuous Tuscan meals when you return home. For more details and the supplemental 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 organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the supplemental costs.
Maid Service - Upgrade your vacation with maid service. This service can be organized by the owner. Ask for more details about the additional cost.
Il Tribbio
Villa delle Palme
Private Property with private pool, A/C, WIFI, TV, terrace, panoramic view, near Montalcino
- 14
- 8
- 7
Description
Villa Delle Palme is located in San Giovanni D'asso, Italy and only 18 km (11 mi) from Montalcino in the tourist area "Orcia Valley". Holiday rental Villa Delle Palme is a lovely property (500 sq m) that includes WiFi internet, air conditioning and private pool. The property can sleep up to 14 people comfortably in eight bedrooms with seven bathrooms.
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of sightseeing. 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 holiday. The kitchen includes coffee machine, toaster 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 terrace is the ideal setting to enjoy food, family and the nice 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: Montalcino 18 km (11 mi), Montepulciano 32 km (20 mi), Siena 45 km (28 mi), Cortona 49 km (30 mi) and Arezzo 54 km (34 mi).
Some other major tourist destinations you should consider visiting are: Florence 133 km (83 mi), Viareggio 220 km (137 mi), Forte Dei Marmi 227 km (141 mi), Rome 215 km (134 mi), Milan 420 km (261 mi) and Naples 406 km (252 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 138 km (86 mi), Pisa (psa) 160 km (99 mi), Roma Ciampino (cia) 224 km (139 mi), Bologna (blq) 225 km (140 mi) and Roma Fiumicino (fco) 237 km (147 mi).
Special Services
Maid Service daily maid service included in the rental price.
Tours The owner can organize custom truffle hunting tours followed by truffle, wine and olive oil tasting for your group. To learn about the tours available, inquire prior to booking to ensure availability. The cost will vary depending on the specific tour and number of people.
Tasting The owner can organize custom truffle, wine and olive oil tasting for your group. To learn more, inquire prior to booking. The cost will vary depending on the number of people.
Painting lessons The owner can organize custom painting lessons with a talented artist for your group. To learn more, inquire prior to booking. The cost will vary depending on the number of people.
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 fun way to spend time with friends and family while learning the techniques required 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 delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Ask for more details and the supplemental costs.
Villa La Consuma
Book your vacation for the period from 01 April 2026 to 16 April 2026 and save 20% (minimum 5 nights). Offer valid until 28 March 2026.
Book your vacation for the period from 17 April 2026 to 09 May 2026 and save 20% (minimum 6 nights). Offer valid until 13 April 2026.
Book your vacation for the period from 10 May 2026 to 30 May 2026 and save 20% (minimum 7 nights). Offer valid until 06 May 2026.
Book your vacation for the period from 06 June 2026 to 20 June 2026 and save 20% (minimum 7 nights). Offer valid until 02 June 2026.
Podere D'Asso
Beautiful private villa with A/C, private pool, WIFI, TV, patio, panoramic view, close to Montalcino
- 12
- 6
- 8
Description
Holiday home Podere D'Asso is a nice stone building (778 sq m) that includes air conditioning, WiFi internet and private pool. The property can accommodate up to 12 guests comfortably in six bedrooms with eight bathrooms. Podere D'Asso is located 2 km (2 mi) from San Giovanni D'asso, Italy and only 20 km (12 mi) from Montalcino in the tourist area "Orcia Valley".
The Experience
When you arrive you’ll find a lovely clean well-maintained property with views of the hills ideal 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. For your pleasure, on the grounds there is a patio and barbecue grill. 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 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the beautiful Tuscan weather.
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: Montalcino 20 km (12 mi), Montepulciano 31 km (19 mi), Siena 47 km (29 mi), Cortona 47 km (29 mi) and Arezzo 53 km (33 mi).
Some other major tourist destinations you should consider visiting are: Florence 132 km (82 mi), Viareggio 219 km (136 mi), Forte Dei Marmi 226 km (140 mi), Rome 214 km (133 mi), Milan 419 km (260 mi) and Naples 405 km (251 mi).
Additional Information
Check-In Time: 15:00 - 20:00
Check-Out Time: 09:00 - 12:00
Pool Open: 20 May - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 200 km (124 mi), Roma Ciampino (cia) 223 km (138 mi), Bologna (blq) 224 km (139 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Additional Services
Cooking Lessons - Learn from a local chef the techniques required to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while discovering the secrets needed to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious 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 - Custom tours can be arranged by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be arranged by the owner. Inquire for more details about the supplemental cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Podere D'Asso. Inquire for more details, including the additional cost and how to organize 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.
Podere Verninelle
- 10
- 5
- 6
Description
You will find Villa Mandorlo inside the ancient Podere di Pomaio, just outside Arezzo. It is an old farmhouse that has been renovated following all of today's eco-sustainability standards, which are similarly applied to the entire estate, which produces and exports excellent Tuscan IGT and DOCG wines. Podere Pomaio's Bio-architecture winery is listed among the 14 most beautiful Design Cellars in Tuscany for the Toscana Wine Architecture project.
At the winery you can also book wine tastings and tours of the estate, we also recommend a visit to the beautiful vineyards, it is an experience not to be missed!
At Villa Mandorlo you will have at your disposal a private garden (about 5000 square metres) and a splendid swimming pool extremely panoramic, overlooking the valley, the surrounding chain of hills and the beautiful city of Arezzo, which, day and night, will offer you truly suggestive sceneries.
In Arezzo you will find all the conveniences of a big city. There are shops, supermarkets and typical restaurants, as well as valuable works of art by renowned artists such as Piero della Francesca and Giorgio Vasari.
The swimming pool, truly splendid, has the particularity of being shell-shaped (size 6.50x8.40 m - depth 1.30 m - open from 01st May to 30th September), and is just a few steps from the bright dining room, definitely one of the highlights of the villa. The dining room, with its large windows, offers not only a fantastic panorama but also the possibility of unforgettable dinners by the pool.
At Villa Mandorlo you will find yourself immersed in the atmosphere and charm of old Tuscan farmhouses. The excellent furnishings and equipment, as well as comfortable and functional, will allow you to spend a memorable holiday.
On the day of your arrival, the owners will be happy to offer you dinner (for stays of a minimum of 7 nights) and a welcome basket with ingredients for breakfast the following day. Villa Mandorlo
- 12
- 6
- 6
Description
If you decide to spend your holiday at Villa Leopoldina, you can stay in a historic building, a splendid example of a typical Tuscan house designed in the 18th century by the architects of Grand Duke Leopold of Lorraine, with the characteristic four overlapping arches on the façade. It will be a plunge into the past, when families were very numerous and these huge homes housed several generations under the same roof.
In front of the villa you will find the private garden and on the right-hand side the beautiful swimming pool (size 12x5 m, depth 1.40 m, completely enclosed - open from 01st May to 30th September). From here, every day, you can enjoy a splendid panoramic view over the city of Arezzo and its valleys, a view that becomes even more suggestive at night with the thousands of tiny lights that seem to chase each other. You will reach the centre of Arezzo in less than 10 minutes by car and here you will find all the necessary amenities and services, as well as museums, magnificent churches, cathedrals and monuments to visit.
One of the villa's bonuses is certainly its location. It is located within the Pomaio winery, a renowned winery that produces its excellent wines following the rules of eco-sustainability. Pomaio is listed as one of the 13 most beautiful Design Cellars in the Region of Tuscany for the Toscana Wine Architecture project, and this 'Green' philosophy was also followed for the renovation of the villa. In fact, thanks to the materials used, the villa has a high energy-saving rating, with positive effects both for the environment and for those who stay there in all seasons.
Therefore, in addition to living in the midst of an almost enchanted place, amidst splendid rows of vines that slope down towards the silhouette of the city, you will be able to taste the excellent wines in the wine cellar when you feel like taking a little walk and reaching it.
Villa Leopoldina is on two levels connected by a covered outdoor staircase. You will have two fully equipped kitchens, a washing machine and a dryer on each floor, Wi-Fi, air conditioning, and satellite TV. Villa Leopoldina is your perfect location for a holiday with all the comforts on an authentic 100-year-old residence.
On arrival day you will have the opportunity to enjoy a dinner offered by the owners (for stays of a minimum of 7 nights) and a welcome basket for breakfast the following day. Thanks to a wooden bridge at the back of the villa, the first floor is also accessible to persons with reduced mobility. Villa Leopoldina
Antica Villa della Lana
Superb private villa with private pool, WIFI, A/C, TV, veranda and pets allowed, close to Arezzo
- 10
- 5
- 5
Description
Vacation rental Antica Villa Della Lana is a nice stone building (220 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to ten people comfortably in five bedrooms with five bathrooms. Antica Villa Della Lana is located 960 m (3115 ft) from Santa Firmina, Italy and only 2 km (2 mi) from Arezzo in the tourist area "Arezzo And Surroundings".
The Experience
After arriving you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax 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.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 2 km (2 mi), Cortona 29 km (18 mi), Montepulciano 51 km (31 mi), Montalcino 72 km (45 mi) and Siena 73 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 93 km (58 mi), Viareggio 179 km (111 mi), Forte Dei Marmi 186 km (116 mi), Rome 232 km (144 mi), Venice 338 km (210 mi) and Milan 381 km (237 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Antica Villa Della Lana. If you have a large dog or multiple pets, please ask for permission prior to booking.
Pool Open: 15 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) 98 km (61 mi), Pisa (psa) 160 km (99 mi), Bologna (blq) 188 km (117 mi), Roma Ciampino (cia) 242 km (150 mi) and Roma Fiumicino (fco) 245 km (152 mi).
Antica Villa Della Lana
Villa Aiale
Unique private villa with private pool, WIFI, A/C, TV, patio, panoramic view, near Montalcino
- 14
- 7
- 8
Description
Villa Aiale is located 2 km (1 mi) from Bibbiano, Italy and only 21 km (13 mi) from Montalcino in the tourist area "Orcia Valley". Vacation rental Villa Aiale is a nice property (500 sq m) that includes WiFi internet, air conditioning and private pool. The property can sleep up to 14 guests comfortably in seven bedrooms with eight bathrooms.
Your Experience
Upon arrival at Villa Aiale you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. After a busy 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. Outdoors you will also find a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people.
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: Montalcino 21 km (13 mi), Siena 38 km (24 mi), Montepulciano 53 km (33 mi), Arezzo 77 km (48 mi) and Cortona 78 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 106 km (66 mi), Viareggio 200 km (124 mi), Forte Dei Marmi 207 km (129 mi), Rome 229 km (142 mi), Milan 400 km (249 mi) and Naples 420 km (261 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 119 km (74 mi), Pisa (psa) 154 km (96 mi), Bologna (blq) 205 km (128 mi), Roma Fiumicino (fco) 232 km (144 mi) and Roma Ciampino (cia) 238 km (148 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques vital 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 learning the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious 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. Inquire for more details and the extra costs.
Tours - The owner can schedule 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 specific tour and number of people.
Maid Service - If you'd like maid service during your visit that can be organized by the owner. Inquire for more details about the additional cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Ask for more details, including the supplemental cost and how to schedule this service.
Villa Aiale
