Luxury Villas with Pool in Monteaperti, Italy
Results 101 - 116 of 116
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Description
Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 36 km (22 mi) from Arezzo. Property La Montana is a nice stone building (145 sq m) that includes private pool, WiFi internet and air conditioning. The property can sleep up to six people comfortably in three bedrooms with three bathrooms.
What to Expect
When you arrive you’ll find a lovely clean well-maintained property with views of the hills and the mountains perfect for a relaxing holiday in Tuscany. After a hectic day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a barbecue grill and playground.
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: Arezzo 36 km (22 mi), Montepulciano 38 km (24 mi), Perugia 59 km (37 mi), Gubbio 67 km (41 mi) and Montalcino 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (73 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 211 km (131 mi), Rome 218 km (136 mi), Milan 404 km (251 mi) and Naples 409 km (254 mi).
Additional Information
Pool Open: 26 April - 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) 123 km (76 mi), Pisa (psa) 185 km (115 mi), Bologna (blq) 209 km (130 mi), Roma Ciampino (cia) 227 km (141 mi) and Roma Fiumicino (fco) 240 km (149 mi).
Additional Services
Tours - Custom tours can be organized 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.
La Montana
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Description
Conveniently located 15 km (9 mi) from Cortona, Italy and only 19 km (12 mi) from Montepulciano. Property Villa Elena is a beautiful property (120 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to seven people comfortably in four bedrooms with two bathrooms.
Your Experience
After arriving you’ll find a beautiful 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 unwind while enjoying a nice cold beverage after a busy day of visiting museums. Also available outdoors are 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 seven people. If you prefer to dine 'al fresco', there is a fully furnished veranda 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 19 km (12 mi), Perugia 49 km (30 mi), Arezzo 53 km (33 mi), Montalcino 55 km (34 mi) and Assisi 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 212 km (132 mi), Forte Dei Marmi 219 km (136 mi), Rome 207 km (129 mi), Milan 412 km (256 mi) and Naples 398 km (247 mi).
Additional Information
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) 130 km (81 mi), Pisa (psa) 193 km (120 mi), Roma Ciampino (cia) 216 km (134 mi), Bologna (blq) 217 km (135 mi) and Roma Fiumicino (fco) 229 km (142 mi).
Additional Services
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 exact tour and number of people.
Villa Elena
Book your vacation for the period from 04 April 2026 to 30 May 2026 and save 10% (minimum 7 nights). Offer valid until 30 May 2026.
Tenuta Pomona
Beautiful independent holiday home with A/C, WIFI, private pool, TV, patio and panoramic view
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Description
Tenuta Pomona is located 9 km (5 mi) from Cortona, Italy and only 28 km (18 mi) from Arezzo in the tourist area "Cortona And Surroundings". Tenuta Pomona is a lovely stone building (189 sq m) with WiFi internet, air conditioning and private pool. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms.
The accommodation consists of the main villa in stone, which can comfortably accommodate up to 6 people and a dependance, where 2 additional guests can stay.
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 city and the hills ideal for a peaceful holiday in Tuscany. After a busy 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. For your pleasure, on the grounds there is a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 28 km (18 mi), Montepulciano 33 km (20 mi), Perugia 55 km (34 mi), Montalcino 67 km (42 mi) and Assisi 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (74 mi), Viareggio 205 km (127 mi), Forte Dei Marmi 212 km (132 mi), Rome 213 km (132 mi), Venice 362 km (225 mi) and Milan 405 km (251 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 186 km (116 mi), Bologna (blq) 210 km (131 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 232 km (144 mi).
More Services
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the additional cost and how to organize this service.
Baby Sitting - A babysitter can be organized at Tenuta Pomona. If you're traveling with kids and would like some alone time, speak to the owner directly about this option after arriving.
Tenuta Pomona
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Description
Villa Luana is located 3 km (2 mi) from Cortona, Italy and only 29 km (18 mi) from Arezzo in the tourist area "Cortona And Surroundings". Property Villa Luana is a beautiful stone building (150 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to eight people comfortably in three bedrooms with four bathrooms.
The Experience
After arriving you’ll find a beautiful clean well-maintained property with views of the hills and the city perfect for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of visiting museums.
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: Arezzo 29 km (18 mi), Montepulciano 32 km (20 mi), Perugia 54 km (33 mi), Montalcino 67 km (42 mi) and Gubbio 72 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 120 km (75 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 214 km (133 mi), Rome 212 km (132 mi), Venice 360 km (224 mi) and Milan 407 km (253 mi).
Additional Information
Pool Open: 15 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 188 km (117 mi), Bologna (blq) 212 km (132 mi), Roma Ciampino (cia) 221 km (138 mi) and Roma Fiumicino (fco) 234 km (145 mi).
Additional Services
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Villa Luana
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Description
Conveniently located in Cortona, Italy in the tourist area "Cortona And Surroundings" and only 29 km (18 mi) from Montepulciano. Villa Il Sasso is a beautiful stone building (450 sq m) with WiFi internet, air conditioning and private pool. The property can sleep up to 13 people comfortably in seven bedrooms with five bathrooms.
Your Experience
After arriving you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the city and the hills perfect for a splendid vacation in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. 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 13 people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the perfect 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: Montepulciano 29 km (18 mi), Arezzo 30 km (18 mi), Perugia 51 km (32 mi), Montalcino 63 km (39 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 127 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 221 km (137 mi), Rome 209 km (130 mi), Venice 370 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 30 April - 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) 135 km (84 mi), Pisa (psa) 195 km (121 mi), Roma Ciampino (cia) 218 km (136 mi), Bologna (blq) 219 km (136 mi) and Roma Fiumicino (fco) 231 km (143 mi).
More Services
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, 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.
Baby Sitting - A babysitter can be scheduled at Villa Il Sasso. If you're traveling with kids and would like some alone time, talk to the owner directly about this option when you arrive.
Villa Il Sasso
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Description
Villa Sole is located 6 km (4 mi) from Cortona, Italy and only 28 km (17 mi) from Arezzo in the tourist area "Cortona And Surroundings". Holiday rental Villa Sole is a beautiful property (350 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to 11 guests comfortably in six bedrooms with five bathrooms.
The Experience
Upon arrival you’ll find a lovely clean well-maintained property perfect for a splendid vacation in Tuscany. After a hectic day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 11 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: Arezzo 28 km (17 mi), Montepulciano 33 km (21 mi), Perugia 54 km (34 mi), Montalcino 68 km (42 mi) and Assisi 75 km (47 mi).
If you'd like to visit the beautiful Tuscan coast, it's just a short driving distance to the sea from the property, only 15 km (9 mi).
Some other major tourist destinations you should consider visiting are: Florence 110 km (68 mi), Viareggio 194 km (121 mi), Forte Dei Marmi 204 km (127 mi), Rome 213 km (133 mi), Venice 353 km (219 mi) and Milan 397 km (246 mi).
Additional Information
Pool Open: 3 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 118 km (73 mi), Pisa (psa) 178 km (111 mi), Bologna (blq) 202 km (126 mi), Roma Ciampino (cia) 222 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
More Services
Tours - The owner can organize custom tours for your group. To learn about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Villa Sole
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Description
Property Villa Delle Rose is a lovely stone building (250 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to eight people comfortably in four bedrooms with four bathrooms. Villa Delle Rose is located 6 km (3 mi) from Cortona, Italy and only 32 km (20 mi) from Arezzo.
What to Expect
When you arrive you’ll find a beautiful clean well-maintained property with views of the mountains and the hills ideal for a splendid vacation in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day.
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 32 km (20 mi), Montepulciano 33 km (20 mi), Perugia 50 km (31 mi), Gubbio 66 km (41 mi) and Montalcino 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 131 km (81 mi), Viareggio 218 km (135 mi), Forte Dei Marmi 225 km (140 mi), Rome 213 km (132 mi), Milan 418 km (260 mi) and Naples 404 km (251 mi).
Additional Information
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) 136 km (85 mi), Pisa (psa) 199 km (123 mi), Roma Ciampino (cia) 222 km (138 mi), Bologna (blq) 223 km (139 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Villa Delle Rose
Villa degli Ulivi
Independent Holiday home with sauna, private pool, hot tub, WIFI, A/C, TV, terrace, panoramic view
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- 4
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Description
Holiday home Villa Degli Ulivi is a lovely stone building (405 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to eight people comfortably in four bedrooms with four bathrooms. Conveniently located in Cortona, Italy in the tourist area "Cortona And Surroundings" and only 29 km (18 mi) from Arezzo.
The property consists of a main building, which can comfortably accommodate up to 8 people and an annex, which can accommodate up to 4 additional guests.
What to Expect
Upon arrival 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, sightseeing, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. 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 eight people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the perfect setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Montepulciano 31 km (19 mi), Perugia 53 km (33 mi), Montalcino 65 km (41 mi) and Gubbio 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (76 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (139 mi), Rome 211 km (131 mi), Venice 372 km (231 mi) and Milan 416 km (258 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) 136 km (85 mi), Pisa (psa) 197 km (122 mi), Bologna (blq) 217 km (135 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
More Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be organized 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 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. Inquire for more details and the additional costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours offered, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Ask for more details, including the additional 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 arranged. Speak to the owner directly about this service upon arrival.
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.
The owners live on the same land, but their house is independent and detached from the rented villa.
Villa Degli Ulivi
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Description
Holiday rental Villa Adelfa is a beautiful stone building (250 sq m) that includes air conditioning, WiFi internet and private pool. The property can sleep up to eight people comfortably in three bedrooms with four bathrooms. Conveniently located 4 km (2 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 30 km (19 mi) from Arezzo.
What to Expect
Upon arrival you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid 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.
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: Arezzo 30 km (19 mi), Montepulciano 33 km (20 mi), Perugia 54 km (34 mi), Montalcino 67 km (42 mi) and Assisi 75 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 121 km (75 mi), Viareggio 208 km (129 mi), Forte Dei Marmi 215 km (133 mi), Rome 213 km (132 mi), Venice 364 km (226 mi) and Milan 406 km (252 mi).
Additional Information
Pool Open: 1 March - 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) 127 km (79 mi), Pisa (psa) 189 km (117 mi), Bologna (blq) 213 km (132 mi), Roma Ciampino (cia) 222 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Special Services
Tours - The owner can arrange custom tours for your group. To learn about the tours offered, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Adelfa
Fonte di Pillo
Wonderful private property with WIFI, private pool, A/C, TV, terrace and panoramic view
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- 6
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Description
Property Summary
Villa Fonte di Pillo is a stunning vacation rental located just 4 kilometers from Gambassi Terme and Castelfiorentino, and 20 kilometers from San Gimignano. This villa offers a peaceful retreat with excellent amenities such as a swimming pool, yard, internet WiFi, parking, and an EV charging station.
Outdoors
The property boasts an impressive 60,000 square meters of land with a well-maintained garden featuring a lawn and various trees. The highlight of the outdoor area is the 12 x 6 meter swimming pool with a depth of 150 centimeters, available seasonally from April 22nd to October 14th. The pool is equipped with an outdoor shower, and the owner/gardener ensures it is always in pristine condition.
Other Information
Inside the villa, guests can enjoy air conditioning and a burglar alarm system for added comfort and security. Access to the property is via a 200-meter-long unmade road, and covered parking is available for up to 2 cars.
Distances and Attractions
Nearby attractions include the cities of Volterra, Firenze, Pisa, and Livorno. Additionally, there is an 18-hole golf course located just 15 kilometers away, making Villa Fonte di Pillo an ideal vacation rental for those seeking relaxation and luxury in a convenient location. Fonte di Pillo
Villa Torreone
Wonderful villa with private pool, WIFI, A/C, TV and panoramic view, close to Cortona
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- 4
- 4
Description
Villa Torreone is located 2 km (1 mi) from Torreone, Italy and only 4 km (3 mi) from Cortona in the tourist area "Cortona And Surroundings". Holiday rental Villa Torreone is a nice stone building (300 sq m) that includes air conditioning, WiFi internet and private pool. The property can sleep up to eight people comfortably in four bedrooms with four bathrooms.
The Experience
When you arrive you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the lake and the mountains ideal for a peaceful 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. 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 eight people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the perfect setting to enjoy food, family and the lovely Tuscan weather.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 4 km (3 mi), Arezzo 32 km (20 mi), Montepulciano 34 km (21 mi), Perugia 55 km (34 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 122 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 214 km (133 mi), Venice 361 km (224 mi) and Milan 406 km (252 mi).
Additional Information
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) 127 km (79 mi), Pisa (psa) 190 km (118 mi), Bologna (blq) 214 km (133 mi), Roma Ciampino (cia) 223 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be organized at the property. It's a enjoyable way to spend time with friends and family while learning the techniques required to master Tuscan cuisine. 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 schedule the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the additional costs.
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your vacation with maid service. This service can be scheduled by the owner. Inquire for more details about the extra cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Ask 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 after arriving.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
The owner lives in the property on the third floor of the villa and has an independent access to the property. Villa Torreone
Villa della Regina
Wonderful private house with private pool, WIFI, hot tub, A/C, TV, patio, close to Montepulciano
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- 7
- 7
Description
Conveniently located 1 km (3273 ft) from Fonte Della Regina, Italy in the tourist area "Orcia Valley" and only 17 km (10 mi) from Montepulciano. Vacation rental Villa Della Regina is a beautiful property (600 sq m) that includes private pool, air conditioning and WiFi internet. The property can accommodate up to 15 guests comfortably in seven bedrooms with seven bathrooms.
Your Experience
Upon arrival you’ll find a beautiful 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. Also available outside are a barbecue grill and patio.
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: Montepulciano 17 km (10 mi), Montalcino 49 km (30 mi), Cortona 58 km (36 mi), Perugia 64 km (40 mi) and Arezzo 68 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 141 km (88 mi), Viareggio 225 km (140 mi), Forte Dei Marmi 235 km (146 mi), Rome 174 km (108 mi), Venice 380 km (236 mi) and Milan 428 km (266 mi).
Additional Information
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) 147 km (91 mi), Roma Ciampino (cia) 183 km (114 mi), Roma Fiumicino (fco) 196 km (122 mi), Pisa (psa) 209 km (130 mi) and Bologna (blq) 233 km (145 mi).
Special Services
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the extra costs.
Villa Conti Galgani
Villa Dorella di Montaperti
Unique private house with A/C, WIFI, private pool, TV, patio, panoramic view, near San Gimignano
- 20
- 10
- 12
Description
Villa Dorella Di Montaperti is a lovely holiday rental (500 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to 20 guests comfortably in ten bedrooms with 12 bathrooms. Villa Dorella Di Montaperti is located 12 km (8 mi) from Volterra, Italy and only 22 km (14 mi) from San Gimignano. There is a golf course nearby if you'd like to get in a round or two while on vacation.
This exclusive rental, in a private, green setting in the Tuscan hills, is the ideal scenario for celebrating your wedding: there is a lovely little 18th century church, still consecrated and adjacent to the villa.
When you arrive at Villa Dorella Di Montaperti you’ll find a lovely clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of shopping. For your pleasure, on the grounds there is a patio and barbecue grill.
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: San Gimignano 22 km (14 mi), Pisa 56 km (35 mi), Siena 58 km (36 mi), Lucca 68 km (42 mi) and Florence 70 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 70 km (43 mi), Viareggio 85 km (53 mi), Forte Dei Marmi 96 km (60 mi), Rome 297 km (184 mi), Venice 315 km (196 mi) and Milan 340 km (211 mi).
Additional Information
Check-In Time: 15:00 - 18:00
Check-Out Time: 07:00 - 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): Pisa (psa) 57 km (36 mi), Firenze Peretola (flr) 73 km (45 mi), Bologna (blq) 164 km (102 mi), Genova (goa) 230 km (143 mi) and Roma Ciampino (cia) 306 km (190 mi).
More Services
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the extra costs.
Maid Service - Upgrade your holiday with maid service. This service can be organized by the owner. Ask for more details about the additional cost.
Villa Montaperti
Villa Chiara
Independent Vacation rental with private pool, A/C, WIFI, TV, terrace, panoramic view, near Cortona
- 8
- 3
- 3
Description
Conveniently located 890 m (2904 ft) from Il Castagno, Italy and only 5 km (3 mi) from Cortona. Holiday home Villa Chiara is a nice stone building (120 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight people comfortably in three bedrooms with three bathrooms.
Your Experience
Upon arrival at Villa Chiara you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - 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. 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 eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
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: Cortona 5 km (3 mi), Montepulciano 29 km (18 mi), Arezzo 33 km (20 mi), Perugia 48 km (30 mi) and Assisi 65 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (76 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (139 mi), Rome 211 km (131 mi), Venice 373 km (231 mi) and Milan 416 km (258 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 136 km (85 mi), Pisa (psa) 197 km (122 mi), Bologna (blq) 217 km (135 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun 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 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 sumptuous 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.
Tours - The owner can schedule custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be arranged at Villa Chiara. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa Chiara
Book your vacation for the period from 30 May 2026 to 06 June 2026 and save 40% (minimum 7 nights). Offer valid until 28 May 2026.
Villa Ivana - Cortona
Independent Villa with hot tub, A/C, WIFI, private pool, TV, patio, panoramic view, near Cortona
- 18
- 9
- 10
Description
Property Villa Ivana - Cortona is a beautiful property (1052 sq m) that includes private pool, WiFi internet and air conditioning. The property can accommodate up to 18 guests comfortably in nine bedrooms with ten bathrooms. Villa Ivana - Cortona is located 2 km (5174 ft) from Ossaia, Italy and only 5 km (3 mi) from Cortona. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
In case the Villa is booked at the reduced price (for groups up to 14 people), the Floor 2 will remain closed.
Your Experience
After arriving you’ll find a beautiful clean well-maintained property ideal for a splendid holiday in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a barbecue grill and patio.
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: Cortona 5 km (3 mi), Montepulciano 29 km (18 mi), Arezzo 32 km (20 mi), Perugia 48 km (30 mi) and Assisi 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 130 km (81 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 212 km (132 mi), Venice 373 km (232 mi) and Milan 416 km (259 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 198 km (123 mi), Roma Ciampino (cia) 221 km (137 mi), Bologna (blq) 222 km (138 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Villa Ivana - Cortona
Cafaggio di Sopra
Wonderful private holiday villa with private pool, WIFI, TV and balcony, near Florence
- 11
- 6
- 3
Description
Property Summary
Nestled in the heart of Tuscany, Italy, the farm estate "Cafaggio di Sopra" is a remarkable holiday rental set in a quiet and elevated position atop a hill, just 8 km from Sieci and 19 km from Florence, in the municipality of Pontassieve. Originally built as a watchtower during the Middle Ages, the main building has been fully renovated and thoughtfully furnished with a harmonious blend of antique and rustic pieces, preserving the authentic character of its historic origins. The property comprises a main house and an annex building, together offering a total of 9 rooms across an impressive 455 m2 of living space. Situated at an altitude of 400 m above sea level, the estate commands breathtaking panoramic views of the rolling Tuscan countryside surrounding Florence, with olive groves, woods, and meadows stretching across the landscape in every direction. Guests have access to a private 6 x 12 m swimming pool, a generous yard that invites relaxation and outdoor enjoyment, and on-site parking reached via a 1 km unmade road. Internet Wi-Fi access is also available, ensuring connectivity throughout your stay.
Outdoors
The outdoor spaces of "Cafaggio di Sopra" are as captivating as the property itself, offering a wealth of areas designed for leisure, dining, and exploration. A charming pergola provides a shaded setting ideal for alfresco meals, complemented by a traditional pizza oven that adds a distinctly Italian touch to outdoor entertaining. The estate is equipped with garden furniture and a barbecue, making it perfectly suited for long, convivial evenings under the Tuscan sky. A children's playground ensures that younger guests are well catered for, while a table tennis table offers additional recreational options for all ages. The surrounding landscape is laced with forest paths leading to a lake, inviting guests to explore the natural beauty of the estate at their own pace. The private swimming pool, measuring 6 x 12 m, serves as the centrepiece of the outdoor area and is set against the stunning backdrop of the hilly Florentine countryside.
Other Information
The main house and annex building of "Cafaggio di Sopra" together form part of a distinguished farm estate, offering a total of 9 rooms across 455 m2. Central heating is available at the property, though it is provided exclusively during the period from 01.11 to 07.04. For guests requiring additional housekeeping services, midweek cleaning can be arranged upon request for an extra fee. For larger groups wishing to make full use of the estate, it is possible to book the entire villa for up to 9 people under the reference IT5270.899.3, in an arrangement that does not include the use of the Suite.
Distances and Attractions
"Cafaggio di Sopra" enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations and practical amenities. The property is situated just 8 km from Sieci and 19 km from Florence, with a train connection to Florence available nearby, offering a convenient and scenic route into the city. Pisa airport is also well connected to the estate, providing straightforward access for international travellers arriving from abroad. Among the nearby attractions, guests will find the charming hilltop town of Fiesole, the prestigious Luxury Outlet The Mall, the picturesque village of Monteloro, and the tranquil forest sanctuary of Vallombrosa. Wine enthusiasts will appreciate the proximity to Greve in Chianti, a quintessential destination in the heart of the Chianti wine region, while San Casciano in Val di Pesa offers further opportunities to discover the authentic flavours and traditions of rural Tuscany. Cafaggio di Sopra
