Tuscany Southeast Villas with Pool
Results 81 - 100 of 414
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Description
La Montanina is a lovely stone building (75 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to four guests comfortably in two bedrooms with two bathrooms. Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 36 km (22 mi) from Arezzo.
Your Experience
Upon arrival at La Montanina you’ll find a beautiful clean well-maintained property with views of the lake and the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outside are a barbecue grill and playground.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: 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).
More Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, 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.
La Montanina
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Description
Holiday home La Montana is a nice stone building (145 sq m) that includes private pool, WiFi internet and air conditioning. The property can accommodate up to six guests comfortably in three bedrooms with three bathrooms. Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 36 km (22 mi) from Arezzo.
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 hills and the mountains ideal 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. Outside you will also find a barbecue grill and playground.
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: 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).
Special Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
La Montana
Villa Chiara
Private Villa with WIFI, private pool, A/C, TV, terrace, panoramic view, close to Cortona
- 8
- 3
- 3
Description
Conveniently located 890 m (2904 ft) from Il Castagno, Italy and only 5 km (3 mi) from Cortona. Villa Chiara is a beautiful stone building (120 sq m) with WiFi internet, air conditioning and private pool. The property can accommodate up to eight guests comfortably in three bedrooms with three bathrooms.
Your Experience
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 splendid 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 unwind at the end the day. 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.
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: 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).
Special Services
Cooking Lessons - If you're interested in learning 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 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 organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Villa Chiara. Inquire for more details, including the supplemental cost and how to arrange this service.
Baby Sitting - A babysitter can be arranged at Villa Chiara. If you're traveling with kids and would like some alone time, speak 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 Oleandro
Pretty private vacation rental with private pool, WIFI, TV, terrace, pets allowed, panoramic view
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- 3
- 2
Description
Holiday rental Villa Oleandro is a lovely stone building that includes WiFi internet and private pool. The property can sleep up to seven guests comfortably in three bedrooms with two bathrooms. Conveniently located 6 km (4 mi) from Cortona, Italy and only 30 km (19 mi) from Montepulciano.
Your Experience
After arriving at Villa Oleandro 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 - 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. 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.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 30 km (19 mi), Arezzo 33 km (21 mi), Perugia 49 km (30 mi), Assisi 66 km (41 mi) and Montalcino 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 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 417 km (259 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Oleandro. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 15 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), Bologna (blq) 218 km (136 mi), Roma Ciampino (cia) 221 km (138 mi) and Roma Fiumicino (fco) 234 km (145 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 delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the supplemental costs.
Tours - The owner can organize custom tours for your group. To learn about the tours available, 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 Oleandro
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Description
Villa for rent in Tuscany near Arezzo.
Located on top of a small hill, set in beautiful unspoiled Tuscan countryside you will find the lovely Villa Ulivi.
The property is just within walking distance from the charming medieval town of Lucignano.
This beautiful, private property offering 6 bedrooms and 7 bathrooms between the main house and the annex, commands amazing views from its terraces and gardens stretching all the way across the Val Di Chiana taking in Castiglion Fiorentino and Cortona.
The Villa has recently undergone total renovation, furnished in very good classic Tuscan taste and yet offering every modern comfort.
This property consists of "Villa Ulivi" and the annex "Casina" and are rented as one property. If your group is eight or less and you don't need the annex "La Casina" it will not be rented during your stay so the property remains private for your group only.
The property, thanks to its spacious interiors and its large exteriors, guarantees a pleasure and safe stay. All the areas, including the swimming pool, are carefully sanitized and sterilized for the health and tranquility of guests.
Distances: Nearest village: Lucignano 650 mt (groceries, restaurants, shops and other services), Arezzo (train station) 30 km, Montepulciano 30 km, Cortona 35 km, Siena, 40 km, Orvieto 85 km, Florence 100 km.
Although immersed in peace and quiet, the A1 Motorway is just 15 minutes drive, connecting you to all-important tourist destinations.
At guests' disposal:
- A wonderful and private pool (12 x 6 mts; depth 1.2/1.5 mts)
- Wi-Fi internet connection
- portable BBQ in the garden.
- parking
Extra Services: dinners & cooking classes available at owners villa which is located on the same property but with plenty of distance between villas to maintain your privacy. The owners speak very good English and can arrange for tours, wine tasting or wedding arrangements. Also cooking classes can be arranged at the owners villa. The owners live about 400 m from the villa. You will be guided to learn the secrets for cooking italian dishes, expecially the one's of the tuscan tradition: You will learn how to make pasta with your hands like tagliatelle, pappardelle, pici, ravioli, tortellini and maccheroni, traditional tuscan dishes like panzanella using bread and vegetables (cucumber tomatoes, onions and fresh basil), tuscan crostini, the secrets to cook perfectly our chianina t-bone on bbq and traditional italian desserts like tiramisu' and "panna cotta" with strawberries and chocolate.
Please carefully check if there are any extra costs to be paid on site! Villa Ulivi
Book 14 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 4 nights minimum and can not be combined with any other special offers.
Villa Fontanelle
Independent Property with internet, private pool, A/C, TV, patio, panoramic view, near Montepulciano
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Description
Villa Fontanelle is located 2 km (1 mi) from Monticchiello, Italy and only 14 km (9 mi) from Montepulciano in the tourist area "Orcia Valley". Villa Fontanelle is a beautiful holiday rental with internet, private pool and air conditioning. The property can sleep up to 14 guests comfortably in seven bedrooms with nine bathrooms.
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property perfect for a peaceful vacation in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. 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 microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 14 km (9 mi), Montalcino 28 km (17 mi), Cortona 46 km (29 mi), Siena 62 km (38 mi) and Arezzo 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 136 km (85 mi), Viareggio 220 km (137 mi), Forte Dei Marmi 230 km (143 mi), Rome 186 km (116 mi), Venice 380 km (236 mi) and Milan 423 km (263 mi).
Additional Information
Pool Open: 9 May - 3 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) 144 km (89 mi), Roma Ciampino (cia) 195 km (121 mi), Pisa (psa) 204 km (127 mi), Roma Fiumicino (fco) 208 km (129 mi) and Bologna (blq) 228 km (142 mi).
More 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 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 additional costs.
Maid Service - If you'd like maid service during your visit that can be arranged by the owner. Inquire for more details about the supplemental cost.
Le Fontanelle
Villa Milluzzi
Amazing independent holiday villa with WIFI, private pool, A/C and TV, close to Cortona
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Description
Holiday home Villa Milluzzi is a beautiful property (320 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to ten guests comfortably in five bedrooms with five bathrooms. Villa Milluzzi is located 1 km (3432 ft) from Ronzano, Italy and only 12 km (8 mi) from Cortona in the tourist area "Cortona And Surroundings".
Your Experience
After arriving you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property ideal 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 unwind at the end the day. Dining 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 coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
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: Cortona 12 km (8 mi), Montepulciano 27 km (17 mi), Arezzo 28 km (17 mi), Montalcino 55 km (34 mi) and Perugia 63 km (39 mi).
If you'd like to visit the beautiful Tuscan coast, it's just a short driving distance to the sea from the vacation rental, only 15 km (9 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 203 km (126 mi), Forte Dei Marmi 213 km (132 mi), Rome 201 km (125 mi), Venice 362 km (225 mi) and Milan 405 km (252 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) 126 km (78 mi), Pisa (psa) 186 km (116 mi), Roma Ciampino (cia) 210 km (130 mi), Bologna (blq) 211 km (131 mi) and Roma Fiumicino (fco) 222 km (138 mi).
More Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Milluzzi
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Description
Conveniently located 6 km (4 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 28 km (17 mi) from Arezzo. Villa Sole is a beautiful vacation rental (350 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to 11 guests comfortably in six bedrooms with five bathrooms.
What to Expect
When you arrive you’ll find a nice clean well-maintained property ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. There is a kitchen including coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 11 people.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: 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 holiday rental, 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 - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Sole
Villa Taragnano
Beautiful independent house with private pool, A/C, WIFI and patio, close to Cortona
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- 5
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Description
Villa Taragnano is located 540 m (1742 ft) from Sant'enea, Italy and only 17 km (10 mi) from Cortona in the tourist area "Cortona And Surroundings". Holiday rental Villa Taragnano is a beautiful stone building (300 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to ten guests comfortably in five bedrooms with three bathrooms.
What to Expect
After arriving at Villa Taragnano you’ll find a beautiful 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 sightseeing. For your pleasure, on the grounds there is a barbecue grill and patio. There is a kitchen including coffee machine 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.
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: Cortona 17 km (10 mi), Arezzo 24 km (15 mi), Montepulciano 43 km (27 mi), Perugia 66 km (41 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 115 km (71 mi), Viareggio 202 km (125 mi), Forte Dei Marmi 209 km (130 mi), Rome 216 km (134 mi), Venice 358 km (223 mi) and Milan 399 km (248 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) 121 km (75 mi), Pisa (psa) 183 km (114 mi), Bologna (blq) 207 km (129 mi), Roma Ciampino (cia) 225 km (140 mi) and Roma Fiumicino (fco) 238 km (148 mi).
Villa Rinaldo
Villa Badia
Superb private holiday home with private pool, WIFI, A/C, TV and pets allowed, close to Arezzo
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- 6
- 4
Description
Villa Badia is a beautiful property (300 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to 12 guests comfortably in six bedrooms with four bathrooms. Villa Badia is located 4 km (3 mi) from Badia Agnano, Italy and only 21 km (13 mi) from Arezzo in the tourist area "Arno Valley".
The Experience
Upon arrival you will be welcomed by the owner or manager where 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 shopping, 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 21 km (13 mi), Cortona 40 km (25 mi), Siena 46 km (28 mi), Montepulciano 51 km (31 mi) and Greve In Chianti 53 km (33 mi).
Some other major tourist destinations you should consider visiting are: Florence 80 km (50 mi), Viareggio 167 km (104 mi), Forte Dei Marmi 174 km (108 mi), Rome 223 km (139 mi), Venice 323 km (201 mi) and Milan 365 km (227 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Badia. If you have a large dog or multiple pets, please ask for permission prior to booking.
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) 86 km (53 mi), Pisa (psa) 148 km (92 mi), Bologna (blq) 172 km (107 mi), Roma Ciampino (cia) 232 km (144 mi) and Roma Fiumicino (fco) 245 km (152 mi).
Villa Caccianello
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- 3
- 2
Description
Holiday home Casa Di Giulio is a nice stone building (100 sq m) that includes WiFi internet. The property can sleep up to five guests comfortably in three bedrooms with two bathrooms. Conveniently located in Vivo D'orcia, Italy in the tourist area "Orcia Valley" and only 34 km (21 mi) from Montalcino.
The pool is shared with the following properties: EAS183985 - EAS 183984 - EAS 183374.
It is possible to book a kit for children which includes: cot with sheets and blanket, changing mat, highchair, baby bathtub and potty, dining set (upon payment)
What to Expect
Upon arrival at Casa Di Giulio you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid holiday 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 unwind at the end the day.
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 34 km (21 mi), Montepulciano 38 km (24 mi), Siena 76 km (47 mi), Cortona 90 km (56 mi) and Perugia 96 km (60 mi).
Some other major tourist destinations you should consider visiting are: Florence 172 km (107 mi), Viareggio 239 km (148 mi), Forte Dei Marmi 250 km (156 mi), Rome 205 km (128 mi), Venice 415 km (258 mi) and Milan 457 km (284 mi).
Additional Information
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) 179 km (111 mi), Roma Ciampino (cia) 215 km (133 mi), Pisa (psa) 215 km (134 mi), Roma Fiumicino (fco) 227 km (141 mi) and Bologna (blq) 264 km (164 mi).
Casa Di Giulio
Book your vacation for the period from 01 April 2026 to 27 June 2026 and save 10% (minimum 4 nights).
Book your vacation for the period from 22 August 2026 to 31 October 2026 and save 10% (minimum 4 nights).
Book your vacation for the period from 22 August 2026 to 31 October 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 01 April 2026 to 27 June 2026 and save 15% (minimum 7 nights).
Villa dei Ciliegi
Private Holiday villa with private pool, WIFI, A/C, patio, panoramic view, close to Cortona
- 8
- 4
- 3
Description
Conveniently located 2 km (5068 ft) from Creti, Italy in the tourist area "Cortona And Surroundings" and only 15 km (9 mi) from Cortona. Property Villa Dei Ciliegi is a lovely property (180 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms.
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 ideal for a splendid 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 unwind at the end the day. Also available outside are a barbecue grill and patio.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 15 km (9 mi), Montepulciano 25 km (16 mi), Arezzo 34 km (21 mi), Montalcino 52 km (32 mi) and Perugia 59 km (37 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 150 m (475 ft).
Some other major tourist destinations you should consider visiting are: Florence 116 km (72 mi), Viareggio 202 km (126 mi), Forte Dei Marmi 210 km (130 mi), Rome 198 km (123 mi), Venice 355 km (221 mi) and Milan 400 km (248 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Dei Ciliegi. If you have a large dog or multiple pets, please inquire for permission prior to booking.
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) 121 km (75 mi), Pisa (psa) 183 km (114 mi), Roma Ciampino (cia) 207 km (128 mi), Bologna (blq) 208 km (129 mi) and Roma Fiumicino (fco) 219 km (136 mi).
Special Services
Cooking Lessons - Discover from a local chef the techniques needed 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 fun way to spend time with friends and family while learning the secrets needed to prepare mouth-watering Tuscan meals when you return home. For more details and the extra cost, please contact us.
Tours - The owner can arrange custom tours for your group. To learn 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.
Villa Dei Ciliegi
Book 7 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Casa Insieme
Pretty independent vacation rental with A/C, private pool, WIFI, terrace and panoramic view
- 12
- 6
- 5
Description
Casa Insieme is a nice stone building (490 sq m) with air conditioning, private pool and WiFi internet. The property can accommodate up to 12 people comfortably in six bedrooms with five bathrooms. Conveniently located 9 km (5 mi) from Asciano, Italy in the tourist area "Orcia Valley" and only 29 km (18 mi) from Siena.
The Experience
After arriving at Casa Insieme you’ll find a beautiful clean well-maintained property with views of the hills ideal 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 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 well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, toaster 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 terrace is the perfect setting to enjoy food, family and the lovely 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: Siena 29 km (18 mi), Montalcino 38 km (23 mi), Montepulciano 44 km (27 mi), Arezzo 53 km (33 mi) and Cortona 54 km (34 mi).
Some other major tourist destinations you should consider visiting are: Florence 98 km (61 mi), Viareggio 192 km (119 mi), Forte Dei Marmi 199 km (124 mi), Rome 221 km (137 mi), Venice 349 km (216 mi) and Milan 390 km (242 mi).
Additional Information
Check-In Time: 15:00 - 19:00
Check-Out Time: 09:00 - 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) 111 km (69 mi), Pisa (psa) 146 km (91 mi), Bologna (blq) 197 km (123 mi), Roma Ciampino (cia) 230 km (143 mi) and Roma Fiumicino (fco) 242 km (151 mi).
Additional Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the specific 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 additional cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Casa Insieme. Inquire for more details, including the additional cost and how to schedule this service.
Casa Insieme
Casale della Torre
Stunning private holiday villa with private pool, A/C, WIFI, TV and panoramic view
- 10
- 5
- 5
Description
Stunning farmhouse with pool dating back to the early 1400s near Cortona, the historical Tuscany hill town with Etruscan roots.
The property is made up of two close stone houses that are rented together to one group of family or friends at a time. The two units have 3 bedrooms and 2 bedrooms, respectively; in total they can comfortably accommodate up to 10 people in tastefully furnished Tuscan-style interiors.
Outdoors there is a large garden lush with plants and flowers, which hosts a lovely private pool and scenic sunbathing area. It is the perfect place for relaxing and cooling off on hot summer days, while taking in the stunning Tuscan landscape. The furnished areas with table, chairs, small armchairs and a barbecue await for comfortable outdoor meals.
Casale della Torre is an ideal base for exploring the entire Cortona area, and is within easy reach of Tuscany and Umbria’s historical areas like Arezzo, Siena, Lake Trasimeno, the Val d'Orcia, Perugia, Gubbio and Assisi.
At guests’ disposal : 5 bedrooms, 5 bathrooms; sleeps 10; air conditioning; private pool (12 x 6 m - minimum depth 1,20 m - maximum depth 2,20 m); sunbathing area with sun loungers and umbrellas; large garden furnished with table and chairs for dining outdoors; barbecue and wood burning oven; laundry room with washing machine and dryer located in an external room; parking on the grounds; panoramic views; Wifi internet.
Distances: Cortona (shops of all kinds) just 1,5 km away, Lake Trasimeno 22 km, Arezzo 33 km, Perugia 50 km, Siena 78 km, Florence (airport) 131 km.
The owners are pleased to offer their guests a barbecue dinner on the property, and access to seasonal produce in the vegetable garden.
Additional dinners can be organized (prices upon request) with local products from the owner’s farm.
Please carefully check if there are any extra costs to be paid on site! Casale Della Torre
Funghi 1
Amazing independent vacation rental with WIFI, private pool, pets allowed and panoramic view
- 9
- 3
- 2
Description
Welcoming, independent stone house with private pool situated a short distance away from the charming town of Pitigliano. This property comprises 2 units rentable only together as a private villa. Outside, guests can enjoy use of a large, well-groomed garden with a nice pool for the sole use of guests.
The property owners live nearby and run a farming estate. A second private villa with pool (of the same owner) is approx. 50 m away and it is available for rent under the name “Funghi 2”.
The nearby town of Pitigliano dating back to the Etruscan time and still preserving its ancient charm, is one of the most beautiful places of interest of the area. The small towns of Sovana and Sorano worth a visit too.
Distances: Pitigliano with shops of all kinds 5 km away, Sovana 12 km, Sorano 15 km, Lake Bolsena 35 km away, Orvieto 50 km, Talamone (beaches) 65 km away, Pienza 75 km, Montalcino 80 km away.
At guests’ disposal: large, fenced-in garden with private, irregular-shaped swimming-pool (circa 8,8 x 3,8 m – min. depth 0,2 m – max. depth 1,3 m), barbecue.
Free WI-FI internet available.
Additional Services: Baby bed upon request. Maid service available by arrangement at € 10,- / per hour (to be paid locally).
Small and medium-sized pets are permitted.
Please carefully check if there are any extra costs to be paid on site! Funghi 1
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.
- 4
- 2
- 3
Description
Beautiful country house situated on the hills of the famous Chianti Classico region, about 20 km from Siena.
This property offers a panoramic view over Chianti area and guarantees privacy and comfort as well as a swimming pool and a large garden with a barbecue area. The interiors are tastefully furnished using materials from Tuscany.
This property is situated in very strategic location that allows you to visit the beauties of the area and discover the most important vineyards of Chianti Classico.
At guests' disposal: private outdoor area, equipped for outdoor dining, swimming pool area shared with the guests of other five adjacent units (fully fenced, so safe for children), large area of gravel equipped with sun loungers and umbrellas, internet connection WI-FI (free of charge), tv satellite tipping, air conditioning in the bedrooms.
Distances: Villa a Sesta (small village of houses with 4 restaurants) approximately 600 meters, Castelnuovo Berardenga with all kinds of shops 7 km, 15 km Gaiole, Radda is 20 km, 30 km Castellina, Rapolano (renowned establishments spa) 20 km, Siena 23 km, San Gimignano 57 km away, Cortona 65 km, Florence and Arezzo 70km, Volterra 81 km, Florence 80 km, Pisa 172 km, Lucca 150 km, Rome 230 km
Please carefully check if there are any extra costs to be paid on site! Casa Maria Luisa
Book 15 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 7 nights minimum and can not be combined with any other special offers.
- 6
- 2
- 2
Description
Dive in the pool of a rental house in Tuscany! Nice villa, share of a house situated in panoramic location on the hills surrounding Cortona. The rental villa, offering extensive views over the Chiana Valley and Lake Trasimeno, has been skilfully restored and turned into 2 comfortable accommodations (one is occupied by the owners). Tuscany country-style, comfortable furnishing.
Distances: a food shop is 2 km away, the charming medieval town of Cortona with all kinds of shops 4 km, Foiano della Chiana with golf course approx. 15 km, Arezzo 30 km, Perugia 45 km. Lake Trasimeno with equipped beaches is in a 20-minute drive. Some beautiful renowned towns like Assisi, Montepulciano, Chianciano Terme and Chiusi are within 40 km. A tennis court is at 2 km. A road passes close by the villa.
At guests’ disposal: large furnished garden, shared swimming pool (9 x 5 m – maximum depth 2,3 m – open from 01/05 to 30/09), barbecue, bread oven. Iron available. Parking within the grounds.
Extra services: Maid service available by arrangement (payment on site).
Please carefully check if there are any extra costs to be paid on site! Casa Ivan
Funghi 2
Unique independent vacation rental with private pool, WIFI, pets allowed and panoramic view
- 7
- 3
- 2
Description
Welcoming, independent stone house with private pool situated a short distance away from the charming town of Pitigliano. This property comprises 2 units rentable only together as a private villa. Outside, guests can enjoy use of a large, well-groomed garden with a nice pool for the sole use of guests.
The property owners live nearby and run a farming estate. A second private villa with pool (of the same owner) is approx. 50 m away and it is available for rent under the name “Funghi 1”.
The nearby town of Pitigliano dating back to the Etruscan time and still preserving its ancient charm, is one of the most beautiful places of interest of the area. The small towns of Sovana and Sorano worth a visit too.
Distances: Pitigliano with shops of all kinds 5 km away, Sovana 12 km, Sorano 15 km, Lake Bolsena 35 km away, Orvieto 50 km, Talamone (beaches) 65 km away, Pienza 75 km, Montalcino 80 km away.
At guests’ disposal: large, fenced-in garden with private, irregular-shaped swimming-pool (circa 11 x 4,6 m – max. depth 1,2 m), barbecue and bread oven. Laundry with washing-machine.
Free WI-FI internet available.
Additional Services: Baby bed upon request. Maid service available by arrangement at € 10,- / per hour (to be paid locally).
Small and medium-sized pets are permitted.
Please carefully check if there are any extra costs to be paid on site! Funghi 2
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.
Villa Morellino
Wonderful accommodation with WIFI, hot tub, private pool, sauna, A/C, terrace and panoramic view
- 12
- 6
- 8
Description
Villa Morellino is a lovely vacation rental (465 sq m) with WiFi internet, air conditioning and hot tub. The property can accommodate up to 12 people comfortably in six bedrooms with eight bathrooms. Conveniently located 13 km (8 mi) from Grosseto, Italy in the tourist area "Grosseto - Maremma" and only 68 km (42 mi) from Montalcino. Experience the Tuscan coast, it's just a short distance to the sea from the holiday home (20 km 12 mi).
Your Experience
Upon arrival at Villa Morellino you’ll find a beautiful clean well-maintained property with views of the hills and the sea ideal for a relaxing 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 shopping. Also available outside are a barbecue grill and hot tub.
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 68 km (42 mi), Siena 87 km (54 mi), Montepulciano 104 km (65 mi), Civitavecchia 108 km (67 mi) and San Gimignano 124 km (77 mi).
Some other major tourist destinations you should consider visiting are: Florence 154 km (96 mi), Viareggio 187 km (116 mi), Forte Dei Marmi 199 km (124 mi), Rome 188 km (117 mi), Venice 401 km (249 mi) and Milan 441 km (274 mi).
Additional Information
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): Pisa (psa) 164 km (102 mi), Firenze Peretola (flr) 167 km (104 mi), Roma Fiumicino (fco) 171 km (106 mi), Roma Ciampino (cia) 193 km (120 mi) and Bologna (blq) 254 km (158 mi).
More Services
Cooking Lessons - Learn from a local chef the techniques vital 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 learning the secrets vital to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
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.
Villa Monte Bottigli
Casa di Pietro in Vivo D'Orcia, Pool
Amazing vacation home with pool, WIFI, TV and panoramic view
- 4
- 2
- 2
Description
Casa Di Pietro In Vivo D'orcia, Pool is a nice stone building (80 sq m) with WiFi internet. The property can sleep up to four guests comfortably in two bedrooms with two bathrooms. Conveniently located in Vivo D'orcia, Italy in the tourist area "Orcia Valley" and only 34 km (21 mi) from Montalcino.
Your Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
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 34 km (21 mi), Montepulciano 38 km (24 mi), Cortona 69 km (43 mi), Siena 76 km (47 mi) and Arezzo 100 km (62 mi).
Some other major tourist destinations you should consider visiting are: Florence 172 km (107 mi), Viareggio 239 km (148 mi), Forte Dei Marmi 250 km (155 mi), Rome 205 km (128 mi), Milan 459 km (285 mi) and Naples 396 km (246 mi).
Additional Information
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) 177 km (110 mi), Roma Ciampino (cia) 214 km (133 mi), Pisa (psa) 215 km (134 mi), Roma Fiumicino (fco) 227 km (141 mi) and Bologna (blq) 264 km (164 mi).
Casa Di Pietro In Vivo D'orcia, Pool
Book your vacation for the period from 01 May 2026 to 01 June 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 11 May 2026 to 25 May 2026 and save 10% (minimum 4 nights).
Book your vacation for the period from 14 June 2026 to 23 June 2026 and save 10% (minimum 4 nights).
Book your vacation for the period from 22 August 2026 to 31 October 2026 and save 10% (minimum 4 nights).
