Luxury Villas with Pool in Montefollonico, Italy
Results 81 - 97 of 97
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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
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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
Villa Trasimena
Private Villa rental with A/C, private pool, sauna, TV, veranda, panoramic view, close to Perugia
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- 5
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Description
Villa Trasimena is a nice holiday home (400 sq m) with air conditioning and private pool. The property can accommodate up to ten guests comfortably in five bedrooms with six bathrooms. Villa Trasimena is located in the centre of Magione, Italy and only 22 km (14 mi) from Perugia in the tourist area "Trasimeno Lake".
Your Experience
After arriving at Villa Trasimena you’ll find a nice clean well-maintained property ideal for a peaceful vacation in Umbria. Regardless of how you spend your days - sightseeing, shopping, 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 Umbria. Dining with friends and family is a big part of the Italian 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 ten people. Dine 'al fresco' like a real Italian, the fully furnished veranda is the perfect setting to enjoy food, family and the lovely Italian 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: Perugia 22 km (14 mi), Cortona 32 km (20 mi), Assisi 43 km (27 mi), Montepulciano 46 km (29 mi) and Gubbio 70 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 147 km (91 mi), Viareggio 233 km (145 mi), Forte Dei Marmi 240 km (149 mi), Rome 196 km (122 mi), Milan 433 km (269 mi) and Naples 387 km (240 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Trasimena. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 19:00
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) 152 km (94 mi), Roma Ciampino (cia) 205 km (127 mi), Pisa (psa) 214 km (133 mi), Roma Fiumicino (fco) 217 km (135 mi) and Bologna (blq) 238 km (148 mi).
Villa Trasimena
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- 8
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Description
Holiday rental Torre Antica is a lovely property (750 sq m) that includes private pool and air conditioning. The property can sleep up to 16 guests comfortably in eight bedrooms with eight bathrooms. Torre Antica is located 7 km (4 mi) from Allerona, Italy and only 48 km (30 mi) from Montepulciano.
Your Experience
After arriving at Torre Antica you’ll find a beautiful clean well-maintained property ideal for a peaceful vacation in Umbria. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Umbria. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine and toaster, as well as, plenty of tableware and cutlery for up to 16 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 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: Montepulciano 48 km (30 mi), Perugia 61 km (38 mi), Cortona 75 km (47 mi), Montalcino 76 km (47 mi) and Assisi 83 km (51 mi).
Some other major tourist destinations you should consider visiting are: Florence 158 km (98 mi), Viareggio 245 km (152 mi), Forte Dei Marmi 252 km (157 mi), Rome 156 km (97 mi), Milan 445 km (276 mi) and Naples 347 km (216 mi).
Additional Information
Check-In Time: 16:00 - 19:00
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) 164 km (102 mi), Roma Ciampino (cia) 172 km (107 mi), Roma Fiumicino (fco) 178 km (110 mi), Pisa (psa) 226 km (140 mi) and Bologna (blq) 250 km (155 mi).
Torre Antica
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- 4
- 2
Description
Holiday home Villa San Leo is a lovely stone building (250 sq m) that includes private pool and WiFi internet. The property can accommodate up to eight guests comfortably in four bedrooms with two bathrooms. Conveniently located 4 km (2 mi) from San Leo Bastia, Italy and only 30 km (19 mi) from Cortona.
Your Experience
After arriving at Villa San Leo you’ll find a nice clean well-maintained property with views of the hills perfect for a relaxing vacation in Umbria. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of visiting museums. There is a kitchen including coffee machine, microwave, toaster 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 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: Cortona 30 km (19 mi), Perugia 48 km (30 mi), Gubbio 52 km (32 mi), Montepulciano 55 km (34 mi) and Arezzo 63 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 156 km (97 mi), Viareggio 242 km (150 mi), Forte Dei Marmi 249 km (155 mi), Rome 237 km (147 mi), Venice 363 km (226 mi) and Milan 423 km (263 mi).
Additional Information
Check-In Time: 15:30 - 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) 161 km (100 mi), Bologna (blq) 222 km (138 mi), Pisa (psa) 223 km (139 mi), Roma Ciampino (cia) 246 km (153 mi) and Roma Fiumicino (fco) 259 km (161 mi).
Villa Betta
Villa del Mangia, 5Panoramic Pool and Chef Service
Superb private holiday rental with WIFI, A/C, private pool, terrace and panoramic view
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- 6
- 6
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).
Il Poggio di Patrignone
Private Holiday villa with WIFI, private pool, hot tub, TV, panoramic view, close to Arezzo
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- 6
- 5
Description
Il Poggio Di Patrignone is a lovely vacation rental (750 sq m) with private pool and WiFi internet. The property can sleep up to 12 guests comfortably in six bedrooms with five bathrooms. Il Poggio Di Patrignone is located 990 m (3220 ft) from Patrignone, Italy and only 8 km (5 mi) from Arezzo in the tourist area "Arezzo And Surroundings".
Your Experience
Upon arrival you’ll find a lovely clean well-maintained property with views of the hills perfect for a relaxing vacation in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of shopping. Also available outdoors are a tennis court 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 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 garden is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
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: Arezzo 8 km (5 mi), Cortona 34 km (21 mi), Montepulciano 55 km (34 mi), Siena 70 km (43 mi) and Greve In Chianti 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 91 km (56 mi), Viareggio 178 km (110 mi), Forte Dei Marmi 185 km (115 mi), Rome 227 km (141 mi), Venice 334 km (207 mi) and Milan 377 km (234 mi).
Consecrated private chapel available upon agreement with the owner.
Dogs are allowed and two large fenced areas (each of 40 sq mt) are available on the property, outside under the pine trees. Maximum 3 dogs allowed. Please note: Dogs are NOT allowed into the villa.
Illuminated tennis court
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Il Poggio Di Patrignone. 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: 2 May - 2 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) 100 km (62 mi), Pisa (psa) 159 km (99 mi), Bologna (blq) 179 km (111 mi), Roma Ciampino (cia) 236 km (147 mi) and Roma Fiumicino (fco) 249 km (155 mi).
Please note: Extra bedroom available for an extra charge with 1 double bed and 2 single bed available for a maximum of 4 people .
Please note: Midweek cleanings are included in the price for a total of 9 weekly hours divided over three days (Monday, Wednesday and Friday).
Please note: The groundskeeper and his wife live in a small property inside the park and totally separated from the main villa. The housekeeper takes daily care of the garden and of the security, the wife takes care of the cleaning.
More Services
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 enjoyable way to spend time with friends and family while learning the secrets needed to prepare delicious 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 delicious meal using local produce? The chef will arrange 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 extra costs.
Tours - Custom tours can be arranged 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 specific tour and number of people.
Maid Service - If you'd like maid service during your trip that can be arranged by the owner. Ask for more details about the supplemental cost.
Il Poggio Cuculo
Villa Conte Jacopo
Superb private holiday home with private pool, A/C, WIFI, TV, patio, panoramic view, near Perugia
- 10
- 6
- 6
Description
Villa Conte Jacopo is a beautiful stone building (520 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to ten people comfortably in six bedrooms with six bathrooms. Conveniently located in Agello, Italy in the tourist area "Trasimeno Lake" and only 19 km (12 mi) from Perugia.
The Experience
After arriving 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 Umbria. 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. Also available outdoors are a patio, barbecue grill and playground. 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 patio where you can enjoy the weather while dining outdoors.
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: Perugia 19 km (12 mi), Assisi 41 km (25 mi), Montepulciano 48 km (30 mi), Cortona 50 km (31 mi) and Gubbio 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 164 km (102 mi), Viareggio 251 km (156 mi), Forte Dei Marmi 258 km (160 mi), Rome 183 km (114 mi), Milan 451 km (280 mi) and Naples 374 km (232 mi).
Additional Information
Handicapped Accessible - If you or one of your guests needs wheelchair access, you’ll find at least one bedroom and bathroom that are accessible, as well as, most of the main rooms in the house.
Check-In Time: 16:00 - 18:00
Check-Out Time: 10:00 - 11:00
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) 169 km (105 mi), Roma Ciampino (cia) 192 km (119 mi), Roma Fiumicino (fco) 204 km (127 mi), Pisa (psa) 232 km (144 mi) and Bologna (blq) 256 km (159 mi).
Special Services
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Ask for more details, including the additional cost and how to schedule this service.
Casale Conte Jacopo
Book 15 days or less before the arrival date and receive a 20 % 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.
Gellino
Fabulous private holiday rental with WIFI, A/C, private pool, TV and panoramic view, near Arezzo
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- 1
- 1
Description
Beautiful small independent house situated in quiet and panoramic location on the hills surrounding Arezzo with extensive views over the surrounding landscape and Arezzo in the distance. This property has been recently restored and offers welcoming, tastefully furnished and romantic interiors. Outside, guests can enjoy use of a well-groomed garden with nice swimming-pool and tennis court.
The property owners live approx. 10 meters away.
Distances: Antria with groceries 2 km away, Arezzo with general stores and railway station 12 km away, the charming town of Cortona 40 km away, Florence 70 km, Rome 150 km away.
At guests’ disposal: large garden with swimming-pool (15 x 8 m - min. depth 1,2 m – max. depth 2,4 m), private tennis court.
This property provides air conditioning.
Parking within the grounds.
Please carefully check if there are any extra costs to be paid on site! Gellino
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Stunning private vacation home with A/C, private pool, WIFI and TV
- 8
- 4
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Description
Holiday home La Dimora del Chianti Dimora: Stunning Tuscan Vill is a lovely property (200 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to eight guests comfortably in four bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Rietine, Italy in the tourist area "Siena And Surroundings" and only 27 km (17 mi) from Siena.
Your Experience
When you arrive at La Dimora del Chianti Dimora: Stunning Tuscan Vill 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, shopping, 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. 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 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.
Montelucci Chianti Agrivilla
Wonderful independent accommodation with A/C, WIFI, private pool, TV, patio and panoramic view
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- 7
- 6
Description
Vacation rental Montelucci Chianti Agrivilla is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to 14 guests comfortably in seven bedrooms with six bathrooms. 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".
Your Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills and the mountains ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and patio. 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 14 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
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: 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 - 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 learning the secrets needed to prepare delicious 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 holiday? 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 additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Montelucci Chianti Agrivilla. Inquire for more details, including the supplemental 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 arranged. Speak to the owner directly about this service upon arrival.
Montelucci Chianti Agrivilla
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- 6
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Description
Conveniently located in Gaiole In Chianti, Italy in the tourist area "Siena And Surroundings" and only 29 km (18 mi) from Siena. Villa Di Gaiole is a lovely stone building (400 sq m) with private pool, WiFi internet and air conditioning. The property can sleep up to 12 guests comfortably in six bedrooms with four bathrooms.
What to Expect
After arriving you’ll find a nice clean well-maintained property with views of the hills ideal 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 unwind at the end the day. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your vacation. The kitchen includes microwave 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 lovely Tuscan weather.
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: 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
Villa Claudia
Stunning independent villa rental with WIFI, private pool, A/C, TV, veranda and panoramic view
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- 5
- 6
Description
Holiday rental Villa Claudia is a nice stone building (260 sq m) that includes private pool, WiFi internet and air conditioning. The property can sleep up to ten people comfortably in five bedrooms with six bathrooms. Villa Claudia is located 1 km (3854 ft) from Montegonzi, Italy and only 35 km (22 mi) from Greve In Chianti in the tourist area "Chianti".
The owners live 50m from the accommodation and have a dog, however their property is totally fenced as well.
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the mountains and the hills ideal for a peaceful 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 unwind at the end the day. 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 ten people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the lovely Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 35 km (22 mi), Arezzo 46 km (29 mi), San Gimignano 55 km (34 mi), Siena 58 km (36 mi) and Florence 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (42 mi), Viareggio 152 km (95 mi), Forte Dei Marmi 162 km (101 mi), Rome 250 km (155 mi), Venice 312 km (194 mi) and Milan 355 km (220 mi).
Additional Information
Check-In Time: 16:30 - 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) 76 km (47 mi), Pisa (psa) 136 km (85 mi), Bologna (blq) 160 km (100 mi), Roma Ciampino (cia) 259 km (161 mi) and Roma Fiumicino (fco) 271 km (169 mi).
Special Services
Bike rental - on request and depending on the availability, you can rent a bike on the spot (cost to be arranged with the owner).
Tour guide - if you are interested, there is the possibility of arranging a guided tour of Florence (on request and against extra costs to be arranged with the owner).
Cooking Lessons - Learn from a local chef the techniques vital to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while discovering the secrets required 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 requirements. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the additional costs.
Villa Claudia
Book your vacation for the period from 25 April 2026 to 09 May 2026 and save 10% (minimum 5 nights). Offer valid until 09 May 2026.
Medieval Castle Living: Vineyards, Swimming Pool &
Lovely holiday home with A/C, WIFI, private pool, balcony and panoramic view, near Siena
- 12
- 6
- 6
Description
Medieval Castle Living: Vineyards, Swimming Pool & is a nice stone building (800 sq m) with WiFi internet, private pool and air conditioning. 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).
Your Experience
When you arrive at Medieval Castle Living: Vineyards, Swimming Pool & you’ll find a lovely clean well-maintained property with views of the hills perfect for a relaxing holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of shopping. For your pleasure, on the grounds there is a playground and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished balcony where you can enjoy the weather while dining outdoors.
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: 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).
Special Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be scheduled at the property. It's a enjoyable 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 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 needs. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the additional costs.
Meals - If you'd like to have meals provided during your stay, either half-board or full-board is available. If you prefer only breakfast be provided, that can be arranged as well. Inquire about the additional costs.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Exclusive Estate Inclusions : elevate your stay, we offer these bespoke services upon reservation:
When you choose the Castle Experience, your stay includes a curated selection of authentic local luxuries:
- Gourmet Farm-to-Table Breakfast: Start your morning in the castle’s elegant common wing with a signature breakfast prepared by the Castellana (the Lady of the Castle). Every ingredient is organic and locally sourced ("Km 0"), with each dish prepared à la minute to your preference upon your arrival at the table.
- Estate Wine Tasting: Enjoy an exclusive guided tour of the castle with a private tasting in the castle’s historic cellar. This experience can be scheduled at your convenience with a simple advance reservation.
Bespoke Guest Experiences (Optional)
To further enhance your Tuscan retreat, we are pleased to arrange the following premium services:
- Dining with the Castellana: Enjoy an elegant, candlelit dinner hosted in the castle's private courtyard—an intimate glimpse into authentic noble life.
- Culinary Arts: Participate in private cooking classes or enjoy professionally catered buffet dinners.
- Outdoor Adventures: Explore the region with curated wine tours, guided bike excursions, or scenic hiking trips through the Montagnola Senese.
- Tuscan Traditions: Experience the thrill of a professional truffle hunting.
Medieval Castle Living: Vineyards, Swimming Pool &
Book now and save 10%. Offer valid until 10 May 2026 and for a minimum stay of 2 nights.
Villa Ombrone
Private Holiday rental with private pool, WIFI, A/C, sauna, TV, patio, pets allowed, panoramic view
- 6
- 3
- 4
Description
Property Villa Ombrone is a beautiful property (160 sq m) that includes air conditioning, WiFi internet and private pool. The property can accommodate up to six people comfortably in three bedrooms with four bathrooms. Conveniently located 12 km (8 mi) from Campagnatico, Italy in the tourist area "Grosseto - Maremma" and only 53 km (33 mi) from Montalcino.
Your Experience
When you arrive you’ll find a nice 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 unwind at the end the day. Also available outside are a playground, patio and barbecue grill.
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: Montalcino 53 km (33 mi), Siena 72 km (45 mi), Montepulciano 89 km (55 mi), San Gimignano 110 km (68 mi) and Greve In Chianti 112 km (69 mi).
Some other major tourist destinations you should consider visiting are: Florence 140 km (87 mi), Viareggio 188 km (117 mi), Forte Dei Marmi 200 km (124 mi), Rome 203 km (126 mi), Venice 386 km (240 mi) and Milan 446 km (277 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Ombrone. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 17:00 - 23:00
Check-Out Time: 06:00 - 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) 148 km (92 mi), Pisa (psa) 165 km (102 mi), Roma Fiumicino (fco) 186 km (115 mi), Roma Ciampino (cia) 208 km (129 mi) and Bologna (blq) 239 km (148 mi).
Villa Ombrone
Book 28 days or less before the arrival date and receive a 15 % discount off the published rental rates.
This Offer is valid only for stays of 4 nights minimum and can not be combined with any other special offers.
- 10
- 5
- 5
Description
Up to 10 guests, 5 beds / 5 baths: this old tuscan farmhouse is located in the heart of the Arno Valley, between Firenze/Florence, Arezzo, Chianti and Siena.
Very centrally located to explore the region, what make this area unique is its authenticity and opportunity to discover Tuscany off the beaten path, thank to our connections: ASK for our concierge service or service list!
Remote but yet very close to nearby towns (about 6 km away from shops, supermarket, train station and highway). You will get to the property by a short private dirt road, driving through vineyards and beautiful mountain and hills views.
Fully immersed in nature and countryside, this is THE getaway to rejoice with nature, silence and breathe Tuscany in every way. The villa is very big, with very spacious rooms and surrounded by greenery and birds singing.
The indoor is typical tuscan, with every comfort such as wifi, wood oven, television with streaming mode and a private Home Cinema!
Wide property with fields and woods for you to take lovely walks around the property, do your yoga sessions or to simply sit under the shade of the pergola. The villa is open also for private events, small weddings, ceremonies or any project we could help realize!
The private pool is 12*5 mt, open from May 1st until Sept 30, with decks, chairs and lots of reading corners!
PETS LIVE ON PROPERTY, housekeeper lives nearby. Villa Marina
Book your vacation for the period from 30 March 2026 to 20 December 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 30 March 2026 to 15 May 2026 and save 10% (minimum 3 nights).
Book 30 days or less before the arrival date and receive a 25 % discount off the published rental rates.
Book 45 days or less before the arrival date and receive a 15 % discount off the published rental rates.
Book 60 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 3 nights minimum and can not be combined with any other special offers.
- 10
- 4
- 2
Description
Villa Sant'anna is a lovely stone building (330 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to ten guests comfortably in four bedrooms with two bathrooms. Villa Sant'anna is located 7 km (5 mi) from Molino Vitelli, Italy and only 36 km (22 mi) from Cortona.
The property consists of a main building and an annex located next to the swimming pool. The annex has a separate entrance from the main building.
What to Expect
When you arrive at Villa Sant'anna you’ll find a nice clean well-maintained property perfect for a splendid holiday in Umbria. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. There is a kitchen including coffee machine, microwave, toaster 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 garden 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: Cortona 36 km (22 mi), Gubbio 40 km (25 mi), Perugia 51 km (32 mi), Arezzo 58 km (36 mi) and Assisi 58 km (36 mi).
Some other major tourist destinations you should consider visiting are: Florence 148 km (92 mi), Viareggio 235 km (146 mi), Forte Dei Marmi 242 km (150 mi), Rome 218 km (135 mi), Venice 358 km (222 mi) and Milan 418 km (260 mi).
Additional Information
Check-In Time: 15:00 - 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) 153 km (95 mi), Pisa (psa) 216 km (134 mi), Bologna (blq) 217 km (135 mi), Roma Ciampino (cia) 227 km (141 mi) and Roma Fiumicino (fco) 239 km (149 mi).
Villa Comunalia
