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Conveniently located 2 km (5121 ft) from Il Castagno, Italy and only 6 km (4 mi) from Cortona. Villa Eleonora is a nice holiday home (170 sq m) with WiFi internet, air conditioning and private pool. The property can accommodate up to eight guests comfortably in four bedrooms with five bathrooms.
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 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 hectic day of sightseeing. For your pleasure, on the grounds there is a patio and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, 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.
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 6 km (4 mi), Montepulciano 30 km (19 mi), Arezzo 33 km (21 mi), Perugia 49 km (30 mi) and Assisi 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 holiday that is not a problem at Villa Eleonora. 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: 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) 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).
Additional Services
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 exact tour and number of people.
Baby Sitting - A babysitter can be scheduled at Villa Eleonora. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa Eleonora
Book your vacation for the period from 28 March 2026 to 02 May 2026 and save 10% (minimum 5 nights). Offer valid until 02 May 2026.
Conveniently located 2 km (5174 ft) from Ossaia, Italy and only 5 km (3 mi) from Cortona. Villa Ivana - Cortona is a beautiful vacation rental (1052 sq m) with WiFi internet, air conditioning and private pool. The property can accommodate up to 18 people comfortably in nine bedrooms with ten bathrooms. 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.
What to Expect
Upon arrival at Villa Ivana - Cortona you’ll find a nice clean well-maintained property ideal for a peaceful 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. For your pleasure, on the grounds there is a patio and barbecue grill.
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 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
Conveniently located 8 km (5 mi) from Montepulciano, Italy in the tourist area "Orcia Valley" and only 36 km (22 mi) from Montalcino. Villa Pianoia is a beautiful holiday home (450 sq m) with air conditioning, WiFi internet and hot tub. The property can sleep up to 16 guests comfortably in seven bedrooms with nine bathrooms.
It is a luxury historic villa that has recently been renovated.
In case of reduced occupancy of 12 guests or fewer, some rooms will remain closed.
The Experience
Upon arrival 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 garden where you can relax while enjoying a nice cold beverage after a busy day of shopping. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. For your pleasure, on the grounds there is a patio, barbecue grill and hot tub. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 16 people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 36 km (22 mi), Cortona 39 km (24 mi), Arezzo 58 km (36 mi), Siena 73 km (46 mi) and Perugia 74 km (46 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 189 km (117 mi), Venice 370 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 136 km (84 mi), Roma Ciampino (cia) 190 km (118 mi), Pisa (psa) 198 km (123 mi), Roma Fiumicino (fco) 200 km (124 mi) and Bologna (blq) 222 km (138 mi).
Special Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a fun way to spend time with friends and family while discovering the techniques needed 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. Inquire for more details and the supplemental costs.
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 individual tour and number of people.
Villa Pianoia
Book 60 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 Petrosa: Your Private Escape Overlooking the is located 2 km (1 mi) from Montepulciano, Italy and only 31 km (19 mi) from Cortona in the tourist area "Orcia Valley". Holiday rental Villa Petrosa: Your Private Escape Overlooking the is a lovely stone building that includes WiFi internet, private pool and air conditioning. The property can accommodate up to ten people comfortably in five bedrooms with six bathrooms.
The 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 hills perfect for a relaxing holiday 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. For your pleasure, on the grounds there is a barbecue grill and patio. 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, 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 patio 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 31 km (19 mi), Montalcino 38 km (24 mi), Arezzo 50 km (31 mi), Siena 66 km (41 mi) and Perugia 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 189 km (117 mi), Venice 365 km (227 mi) and Milan 409 km (254 mi).
Additional Information
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) 128 km (79 mi), Pisa (psa) 190 km (118 mi), Roma Ciampino (cia) 198 km (123 mi), Roma Fiumicino (fco) 211 km (131 mi) and Bologna (blq) 214 km (133 mi).
Special Services
Cooking Lessons - Learn from a local chef the techniques required to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while learning the secrets required to prepare delicious Tuscan meals when you return home. For more details and the additional cost, please contact us.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Inquire for more details, including the extra cost and how to schedule this service.
Villa Petrosa: Your Private Escape Overlooking the
Property Summary
Nestled just 900 metres from the historic centre of Montepulciano, in the heart of Tuscany, Italy, Villa Incanto is an exceptional country house that offers a refined and immersive holiday experience for those seeking elegance, privacy, and natural beauty. The property is composed of 2 stone buildings that have been recently and carefully renovated, blending modern elegant details with traditional architectural character to create an atmosphere of timeless sophistication. Surrounded by a generous yard filled with olive trees, a variety of flowers, and ancient roses, the estate provides a serene and picturesque setting that reflects the very essence of the Tuscan countryside. Guests can enjoy the convenience of on-site parking, stay seamlessly connected with Internet WiFi available throughout all rooms, and take advantage of the private swimming pool, which offers breathtaking views of Montepulciano. A tennis court is also available on the property, adding a further dimension of leisure and recreation to the stay. From the villa, the remarkable skyline of Montepulciano, long celebrated as the pearl of the 15th century and one of the most beautiful cities in the Tuscan region, can be admired in all its splendour.
Outdoors
The outdoor spaces of Villa Incanto are thoughtfully designed to complement the natural landscape and invite guests to fully embrace the beauty of the surrounding environment. The private swimming pool is the centrepiece of the exterior, positioned to capture sweeping views of Montepulciano and equipped with sunbeds and an umbrella to ensure comfort during warm sunny days. A covered gazebo furnished with garden furniture provides a shaded and elegant space for relaxation or informal gatherings in the open air. Several of the suites benefit from direct access to the garden, ensuring an exceptional level of privacy and a seamless connection between the interior living spaces and the lush outdoor surroundings. The garden itself, abundant with olive trees, diverse flowering plants, and ancient roses, creates a tranquil and fragrant atmosphere that enhances every moment spent outdoors. A barbecue is also available, making al fresco dining a natural and pleasurable part of the villa experience.
Other Information
Villa Incanto has been carefully restored to preserve its authentic stone character while introducing a series of refined interior comforts that cater to the expectations of discerning guests. The bathrooms are finished with natural rocks or mosaic detailing, and showers are equipped with hydromassage jets, reflecting the high standard of craftsmanship applied throughout the renovation. Air conditioning is available to ensure comfort during warmer months, while a beautiful working fireplace adds warmth and atmosphere during cooler evenings. The dining room is a particularly striking space, featuring large glass windows that frame extraordinary views of the surrounding landscape, making every meal a visually memorable occasion. Internet WiFi is accessible in all rooms, ensuring guests remain connected throughout their stay without compromising the sense of retreat that the property naturally provides.
Distances and Attractions
Villa Incanto enjoys an outstanding location that places guests within easy reach of some of the most celebrated destinations in central Italy. Montepulciano itself is just 900 metres away, offering an extraordinary concentration of Renaissance architecture, world-renowned Vino Nobile wine, fine dining, and cultural heritage that has earned it the historic title of "the pearl of the 15th century." The villa's position is equally ideal for exploring the wider beauty of both Tuscany and the neighbouring Umbria region, accessible comfortably by car. The nearby town of Chianciano Terme, one of the closest towns to the property, is well known for its celebrated thermal baths and also hosts a train station from which guests can conveniently travel to Florence or Rome, making longer excursions across Italy entirely feasible. Villa Incanto
Conveniently located 2 km (1 mi) from Pergo, Italy and only 7 km (4 mi) from Cortona. Holiday rental Villa Gelsomino is a nice stone building (260 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to eight guests comfortably in four bedrooms with three bathrooms.
The Experience
When you arrive you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid 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. Outside you will also find a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 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 holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 7 km (4 mi), Arezzo 34 km (21 mi), Montepulciano 35 km (22 mi), Perugia 53 km (33 mi) and Gubbio 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (142 mi), Rome 217 km (135 mi), Venice 378 km (235 mi) and Milan 422 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Gelsomino. 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: 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) 142 km (88 mi), Pisa (psa) 203 km (126 mi), Bologna (blq) 223 km (139 mi), Roma Ciampino (cia) 226 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
More Services
Cooking Lessons - Learn 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 required to prepare mouth-watering 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 requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the additional costs.
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 ask prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - A babysitter can be arranged at Villa Gelsomino. If you're traveling with kids and would like some alone time, talk to the owner directly about this option upon arrival.
Villa Gelsomino
Conveniently located 3 km (2 mi) from Pergo, Italy and only 8 km (5 mi) from Cortona. Villa Il Borgo is a beautiful stone building (240 sq m) with air conditioning, WiFi internet and private pool. The property can accommodate up to eight guests comfortably in four bedrooms with four bathrooms.
The Property is composed of the main Villa and an annex.
What to Expect
Upon arrival at Villa Il Borgo 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 relax while enjoying a nice cold beverage after a busy day of visiting museums. Outdoors you will also find a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, 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 patio where you can enjoy the weather while dining outdoors.
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 8 km (5 mi), Arezzo 35 km (22 mi), Montepulciano 37 km (23 mi), Perugia 54 km (34 mi) and Gubbio 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 137 km (85 mi), Viareggio 224 km (139 mi), Forte Dei Marmi 231 km (143 mi), Rome 219 km (136 mi), Venice 380 km (236 mi) and Milan 422 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Il Borgo. 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: 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) 142 km (88 mi), Pisa (psa) 205 km (127 mi), Roma Ciampino (cia) 228 km (142 mi), Bologna (blq) 229 km (142 mi) and Roma Fiumicino (fco) 240 km (149 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be arranged at the property. It's a fun way to spend time with friends and family while discovering the techniques vital to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. 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 available, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
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.
Villa Il Borgo
Villa Bartolomeo is located 3 km (2 mi) from Bivio Di San Biagio, Italy and only 5 km (3 mi) from Montepulciano in the tourist area "Orcia Valley". Villa Bartolomeo 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 six bathrooms.
The Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of shopping.
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: Montepulciano 5 km (3 mi), Cortona 36 km (22 mi), Montalcino 36 km (23 mi), Arezzo 55 km (34 mi) and Siena 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 127 km (79 mi), Viareggio 211 km (131 mi), Forte Dei Marmi 221 km (137 mi), Rome 186 km (115 mi), Venice 366 km (228 mi) and Milan 414 km (257 mi).
Additional Information
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) 133 km (82 mi), Pisa (psa) 195 km (121 mi), Roma Ciampino (cia) 195 km (121 mi), Roma Fiumicino (fco) 207 km (129 mi) and Bologna (blq) 219 km (136 mi).
Additional Services
Cooking Lessons - Learn from a local chef the techniques required 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 vital to prepare sumptuous 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 mouth-watering meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the supplemental costs.
Villa Benefizio
Castello D'Ombrone is a lovely holiday rental with private pool, WiFi internet and air conditioning. The property can sleep up to 18 people comfortably in nine bedrooms with eight bathrooms. Conveniently located 6 km (3 mi) from Buonconvento, Italy in the tourist area "Orcia Valley" and only 18 km (11 mi) from Montalcino. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
The property is located within a wildlife reserve, which is why wild animals can sometimes be seen on the grounds. However, they usually do not come close to the houses.
What to Expect
When you arrive at Castello D'Ombrone you’ll find a beautiful clean well-maintained property perfect for a peaceful vacation 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 18 km (11 mi), Siena 35 km (21 mi), Montepulciano 45 km (28 mi), Arezzo 68 km (42 mi) and Cortona 71 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 102 km (63 mi), Viareggio 196 km (122 mi), Forte Dei Marmi 203 km (126 mi), Rome 221 km (137 mi), Venice 353 km (219 mi) and Milan 394 km (245 mi).
Additional Information
Check-In Time: 15:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 29 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) 117 km (72 mi), Pisa (psa) 150 km (93 mi), Bologna (blq) 201 km (125 mi), Roma Ciampino (cia) 230 km (143 mi) and Roma Fiumicino (fco) 242 km (151 mi).
Special 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 pleasant way to spend time with friends and family while learning the techniques needed to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Maid Service - If you'd like maid service during your visit that can be organized by the owner. Ask for more details about the supplemental cost.
Borgo Castelrotto
Villa Monticchiello is a stunning property set in one of most amazing Tuscan area Val D’Orcia protected by the UNESCO; the villa is on a little hill and offers amazing views of the characteristics surrounding hills and the wonderful historic city of Pienza famous for its unique Pecorino cheese some of the most important Tuscan wineries are born in this area including probably the most famous Brunello di Montalcino, the villa has also easy access to the little hamlet of Monticchiello which offers some grocery and restaurant of course.
The villa has a spectacular perfectly maintained garden which surrounds the property and offers to its guests a private swimming pool of 15x5 mt depth from 0.90 to 1.70 mt. equipped with sun beds.
there is a covered area with a barbecue fireplace and pizza oven where to prepare al fresco meals set in a unique position which would offer guests some of the most unforgettable sunsets.
The paved portico is elegantly equipped with garden sofas and chairs in order to offer a relaxing outdoor area where to enjoy a glass of Brunello wine admiring the landscape. Villa Montichiello
Case Sant'anna is a beautiful holiday rental (300 sq m) with WiFi internet, hot tub and air conditioning. The property can sleep up to 18 people comfortably in nine bedrooms with eight bathrooms. Case Sant'anna is located 9 km (6 mi) from Terontola, Italy and only 12 km (8 mi) from Cortona. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
Outdoor Jacuzzi, Included in rental price. Open during the same period of the swimming pool.
Please note that the garden is not fenced.
Truffle hunting experience in the proximity of the property, to be requested at the time of booking
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property ideal for a peaceful vacation in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. Also available outside are a barbecue grill, patio and hot tub.
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: Cortona 12 km (8 mi), Montepulciano 26 km (16 mi), Arezzo 36 km (22 mi), Perugia 52 km (32 mi) and Montalcino 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 211 km (131 mi), Forte Dei Marmi 218 km (135 mi), Rome 206 km (128 mi), Venice 367 km (228 mi) and Milan 410 km (255 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Case Sant'anna. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:30 - 21:00
Check-Out Time: 06:00 - 10:00
Pool Open: 20 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) 131 km (82 mi), Pisa (psa) 192 km (119 mi), Roma Ciampino (cia) 215 km (134 mi), Bologna (blq) 218 km (135 mi) and Roma Fiumicino (fco) 228 km (141 mi).
Case Sant'anna
Conveniently located 550 m (1795 ft) from Il Passaggio, Italy and only 6 km (4 mi) from Cortona. Villa Mimosa is a lovely property (175 sq m) with WiFi internet, air conditioning and private pool. The property can sleep up to ten people comfortably in five bedrooms with two bathrooms.
The Experience
After arriving you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid vacation 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. Also available outdoors are a patio and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
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: Cortona 6 km (4 mi), Arezzo 34 km (21 mi), Montepulciano 35 km (22 mi), Perugia 53 km (33 mi) and Gubbio 63 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (142 mi), Rome 217 km (135 mi), Venice 378 km (235 mi) and Milan 421 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Mimosa. 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: 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) 142 km (88 mi), Pisa (psa) 203 km (126 mi), Bologna (blq) 223 km (139 mi), Roma Ciampino (cia) 226 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
Additional Services
Cooking Lessons - Discover 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 pleasant way to spend time with friends and family while discovering the secrets vital to prepare mouth-watering Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will organize 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.
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service after arriving.
Villa Mimosa
Conveniently located 1 km (4646 ft) from Terontola, Italy and only 10 km (6 mi) from Cortona. Holiday home Villa Lilli & Spa is a beautiful stone building (200 sq m) that includes air conditioning, hot tub and private pool. The property can sleep up to six people comfortably in three bedrooms with three bathrooms.
What to Expect
After arriving at Villa Lilli & Spa you’ll find a nice clean well-maintained property with views of the city and the mountains perfect for a relaxing 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. For your pleasure, on the grounds there is a barbecue grill, hot tub 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 six people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting 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 10 km (6 mi), Montepulciano 28 km (18 mi), Arezzo 35 km (21 mi), Perugia 44 km (27 mi) and Montalcino 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (138 mi), Rome 211 km (131 mi), Milan 416 km (258 mi) and Naples 402 km (249 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) 134 km (83 mi), Pisa (psa) 197 km (122 mi), Roma Ciampino (cia) 220 km (136 mi), Bologna (blq) 221 km (137 mi) and Roma Fiumicino (fco) 232 km (144 mi).
Additional Services
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
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 supplemental cost and how to organize this service.
Villa Lilli & Spa
Holiday rental Case Sant'anna 14 is a beautiful property (230 sq m) that includes hot tub, air conditioning and WiFi internet. The property can accommodate up to 14 guests comfortably in seven bedrooms with six bathrooms. Conveniently located 9 km (6 mi) from Terontola, Italy and only 12 km (8 mi) from Cortona. There is a golf course nearby if you'd like to get in a round or two while on holiday.
The Experience
The property Case Sant'Anna is completely independent.
Truffle hunting experience in the proximity of the property, to be requested at the time of booking
Outdoor Jacuzzi, included in the rental price. Open during the same period of the swimming-pool.
After arriving you’ll find a lovely clean well-maintained property perfect for a splendid vacation 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. Also available outdoors are a patio, barbecue grill and hot tub. 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 patio 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 12 km (8 mi), Montepulciano 26 km (16 mi), Arezzo 36 km (22 mi), Perugia 52 km (32 mi) and Montalcino 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 211 km (131 mi), Forte Dei Marmi 218 km (135 mi), Rome 206 km (128 mi), Venice 367 km (228 mi) and Milan 410 km (255 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Case Sant'anna 14. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 21:00
Check-Out Time: 06:00 - 10:00
Pool Open: 20 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) 131 km (82 mi), Pisa (psa) 192 km (119 mi), Roma Ciampino (cia) 215 km (134 mi), Bologna (blq) 218 km (135 mi) and Roma Fiumicino (fco) 228 km (141 mi).
Case Sant'anna 14
Capanna Al Lago is located 8 km (5 mi) from Siena, Italy and only 35 km (22 mi) from Greve In Chianti in the tourist area "Siena And Surroundings". Capanna Al Lago is a lovely stone building (200 sq m) with air conditioning, hot tub and private pool. The property can sleep up to six people comfortably in three bedrooms with three bathrooms.
The Experience
After arriving at Capanna Al Lago you’ll find a nice clean well-maintained property with views of the lake 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. Outdoors you will also find a patio, playground, barbecue grill and hot tub. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to six 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: Greve In Chianti 35 km (22 mi), San Gimignano 36 km (22 mi), Montalcino 48 km (30 mi), Florence 66 km (41 mi) and Montepulciano 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 66 km (41 mi), Viareggio 160 km (99 mi), Forte Dei Marmi 167 km (104 mi), Rome 244 km (151 mi), Venice 316 km (196 mi) and Milan 360 km (224 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 10 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) 79 km (49 mi), Pisa (psa) 114 km (71 mi), Bologna (blq) 165 km (103 mi), Roma Ciampino (cia) 253 km (157 mi) and Roma Fiumicino (fco) 265 km (165 mi).
Additional Services
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Capanna Al Lago. Inquire for more details, including the extra cost and how to arrange this service.
Capanna Al Lago
Book your vacation for the period from 08 April 2026 to 23 April 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 15 August 2026 to 23 August 2026 and save 10% (minimum 3 nights).
Conveniently located 2 km (1 mi) from Montanare, Italy in the tourist area "Cortona And Surroundings" and only 9 km (6 mi) from Cortona. Casale Montanare is a lovely stone building (220 sq m) with WiFi internet and private pool. The property can accommodate up to ten people comfortably in five bedrooms with six bathrooms.
The swimming pool site is a short walk up a beautiful garden path, 70 mt distant from the villa.
Your Experience
After arriving you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the mountains and the hills perfect for a relaxing vacation 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany. 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 ten people.
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 9 km (6 mi), Arezzo 37 km (23 mi), Montepulciano 37 km (23 mi), Perugia 55 km (34 mi) and Gubbio 63 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 136 km (84 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (143 mi), Rome 217 km (135 mi), Venice 375 km (233 mi) and Milan 420 km (261 mi).
Additional Information
Check-In Time: 15:00 - 17:00
Check-Out Time: 07:00 - 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) 141 km (88 mi), Pisa (psa) 203 km (126 mi), Roma Ciampino (cia) 226 km (141 mi), Bologna (blq) 227 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
Special Services
Cooking Lessons - Learn 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 sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your 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 suggestions for the various courses and the wine. Inquire for more details and the extra costs.
Il Rifugio
Property Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky is a lovely property (200 sq m) that includes hot tub, WiFi internet and air conditioning. The property can sleep up to eight people comfortably in four bedrooms with three bathrooms. Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky is located in Siena, Italy and only 38 km (24 mi) from San Gimignano in the tourist area "Siena And Surroundings".
The Experience
When you arrive at Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky you’ll find a beautiful clean well-maintained property with views of the hills perfect for a relaxing 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 for a perfect ending to another day in Tuscany. Outside you will also find a hot tub, patio and barbecue grill. 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.
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: San Gimignano 38 km (24 mi), Greve In Chianti 40 km (25 mi), Montalcino 43 km (27 mi), Montepulciano 62 km (39 mi) and Florence 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (42 mi), Viareggio 162 km (101 mi), Forte Dei Marmi 169 km (105 mi), Rome 239 km (148 mi), Venice 318 km (198 mi) and Milan 362 km (225 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 30 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) 81 km (50 mi), Pisa (psa) 116 km (72 mi), Bologna (blq) 167 km (104 mi), Roma Ciampino (cia) 248 km (154 mi) and Roma Fiumicino (fco) 261 km (162 mi).
More Services
Tours - Custom tours can be organized 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.
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky
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).
Villa Torre del Chianti is a unique property in the heart of the Chianti reagion in Tuscany, a step away from Radda in Chianti, surrounded by the world wide famous Chianti wineries. A peaceful location where guests can admire of the harmonious Chianti hills that are offering spectacular views with unique sunsets. From the villa is easy to access most of the historic cities and towns of Tuscany such as Florece, Siena, San Gimignano, the area is full of castles and antique monasteries producing local food and wine on where client can organize day trips.
The villa has a private fenced garden which surround the entire property, the villa owner also produce wine and can organize tasting at the property or to the wineries with the visit of the fields. The garden features a magnificent private swimming pool of 12x6 mt. depth 1.40 to 2.00 mt. (pool can be heated upon request) equipped with elegant sun beds umbrella and gazebo, there is also a playground for children. There is a covered are with table chairs and Barbeque where to enjoy al fresco meals. Villa Torre del Chianti
Property Pozza Di Volpaia is a lovely stone building (300 sq m) that includes private pool and WiFi internet. The property can accommodate up to 11 people comfortably in six bedrooms with five bathrooms. Pozza Di Volpaia is located in the centre of Volpaia, Italy and only 23 km (14 mi) from Greve In Chianti in the tourist area "Chianti".
The Experience
This property is located in the fortified medieval hamlet of Volpaia, in the Chianti Classico area, in a secluded position ensuring complete privacy. It is just a 300 m walk to the centre of the hamlet, with 2 restaurants, one of which managed by the Castello di Volpaia farm, where it is possible to taste the local cuisine. Cooking classes are also arranged, on request, by the English-speaking local office.
Upon arrival at Pozza Di Volpaia you’ll find a lovely clean well-maintained property with views of the hills perfect 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 busy day of sightseeing. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 11 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Tuscan weather.
Places Nearby
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 23 km (14 mi), Siena 41 km (26 mi), San Gimignano 51 km (32 mi), Florence 53 km (33 mi) and Arezzo 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 53 km (33 mi), Viareggio 149 km (93 mi), Forte Dei Marmi 156 km (97 mi), Rome 257 km (159 mi), Venice 305 km (190 mi) and Milan 348 km (216 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) 70 km (43 mi), Pisa (psa) 114 km (71 mi), Bologna (blq) 150 km (93 mi), Roma Ciampino (cia) 272 km (169 mi) and Roma Fiumicino (fco) 284 km (177 mi).
Additional Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, ask about the cooking lessons that can be arranged 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.
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 specific tour and number of people.
Maid Service - Upgrade your vacation with maid service. This service can be arranged by the owner. Ask for more details about the extra cost.
Cleaning service is included 4 hours a day 5 days a week. Pozza Di Volpaia