Colombaio Vacation Villa Rentals
Results 181 - 200 of 454
Villa degli Olivi
Private Property with A/C, WIFI, private pool, TV, terrace, pets allowed, near Arezzo
- 14
- 7
- 7
Description
Villa degli Olivi is a beautiful holiday villa with attractive architectural features situated just outside Castiglion Fiorentino, a typical Tuscan town on the hills of the Valdichiana, surrounded by age-old olive groves and ancient cypress trees. The origins of the town date back in history. Today it's a quiet town which offers its visitors numerous cultural and eno-gastronomic events planned throughout the whole year.
The villa is situated on the slopes of a hill looking onto the Valdichiana below and is certainly the ideal spot for anyone wanting to spend their holiday in a charming country villa, without sacrificing any of the comforts of modern life. The internal fittings, equipment and furnishings of the house are of an high standard and ensure the maximum comfort.
Around the villa a large park of centuries-old olive trees, completely fenced in with a fence and equipped with gazebo, garden furniture, barbecue and wood-burning oven will be the ideal place to spend relaxing evenings in good company. For the amusement of adults and children there are: the beautiful fenced-in infinity pool (size m. 6 x 12, depth m. 1,20-3,00 - open from 01st May to 30th September), the table tennis and approx. 2 km far the private tennis court (size 18x36 m.) to be shared only with the guests of other 3 villas COLLINA DEI FIORI, CASALE IL TRECENTO and VILLA GIOTTO. Villa degli Olivi
- 3
- 10
- 3
- 3
| Accommodation | |||||
|---|---|---|---|---|---|
| Il Susino | 2 | 1 | 1 | ||
| Il Ciliegio | 4 | 1 | 1 | ||
| Il Pesco | 4 | 1 | 1 | ||
| All 3 Accommodations | 10 | 3 | 3 |
Description
Pozzonovo is an old farmhouse divided into 3 comfortable apartments and is the result of the skilful and careful renovation of a stone building. The three units have independent entrances and in the garden their own area equipped with a table, chairs, sun umbrella and barbecue, perfect for enjoying your meals in the open air.
You will find the farmhouse immersed in the Valdichiana countryside and, at the same time, close to the village of Castiglion Fiorentino, which can be easily reached on foot with a walk of about 1.5 km. From the railway station in Castiglion Fiorentino it will be easy to travel by train for day trips to Florence, Rome and other interesting cities in central Italy.
We advise you to immerse yourself in the life of the small village, its shops, bars and restaurants; you will get a glimpse of country life that still harks back to ancient traditions and customs.
The stone walls, wooden and brick ceilings and simple but comfortable furnishings give the apartments a special charm. You will immediately feel at home, welcomed by a warm atmosphere and by Mrs Rita, the owner, who is always ready to assist her guests in times of need.
Together with the owner, you will be able to make use of the large outdoor area, a cool, large 6 x 12 m swimming pool (depth 0.90-1.40 m - open from 01 May to 30 September) located in front of the house, the badminton court, table tennis and bowling green.
Internet access available only in the garden. Pozzonovo
Villetta di Cortona
Private House with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view
- 4
- 2
- 2
Description
Villetta Di Cortona is a nice holiday rental (90 sq m) with WiFi internet, private pool and air conditioning. The property can accommodate up to four people comfortably in two bedrooms with two bathrooms. Villetta Di Cortona is located 12 km (7 mi) from Cortona, Italy and only 22 km (14 mi) from Montepulciano.
The Experience
After arriving you’ll find a nice clean well-maintained property perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of visiting museums. Outdoors you will also find a patio and barbecue grill.
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: Montepulciano 22 km (14 mi), Perugia 49 km (30 mi), Arezzo 49 km (30 mi), Montalcino 57 km (35 mi) and Siena 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 121 km (75 mi), Viareggio 207 km (129 mi), Forte Dei Marmi 214 km (133 mi), Rome 202 km (126 mi), Venice 364 km (226 mi) and Milan 407 km (253 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villetta Di Cortona. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 19:00
Check-Out Time: 06:00 - 09:00
Pool Open: 15 April - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 128 km (79 mi), Pisa (psa) 188 km (117 mi), Roma Ciampino (cia) 212 km (131 mi), Bologna (blq) 212 km (132 mi) and Roma Fiumicino (fco) 224 km (139 mi).
The garden is fully enclosed.
Up to 3 dogs are accepted. Villino Cortona
Book your vacation for the period from 04 April 2026 to 16 May 2026 and save 25% (minimum 3 nights).
Book your vacation for the period from 26 September 2026 to 28 November 2026 and save 25% (minimum 3 nights).
- 6
- 4
- 2
Description
Valdambra Villa is located in the centre of Vepri, Italy and only 29 km (18 mi) from Arezzo in the tourist area "Arno Valley". Property Valdambra Villa is a lovely stone building (170 sq m) that includes private pool, WiFi internet and hot tub. The property can accommodate up to six guests comfortably in four bedrooms with two bathrooms.
This villa can accommodate up to a maximum of 6 guests, infants included.
The owners live near the property and will always be available for any request.
What to Expect
Upon arrival at Valdambra Villa you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of shopping. For your pleasure, on the grounds there is a hot tub and barbecue grill. Dining 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 and refrigerator, as well as, plenty of tableware and cutlery for up to six people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the perfect setting to enjoy food, family and the beautiful Tuscan weather.
Places Nearby
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Siena 40 km (25 mi), Greve In Chianti 48 km (30 mi), Montepulciano 55 km (34 mi) and Cortona 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 160 km (99 mi), Forte Dei Marmi 170 km (105 mi), Rome 232 km (144 mi), Venice 319 km (198 mi) and Milan 363 km (225 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 83 km (52 mi), Pisa (psa) 144 km (89 mi), Bologna (blq) 168 km (104 mi), Roma Ciampino (cia) 241 km (150 mi) and Roma Fiumicino (fco) 253 km (157 mi).
Villa Vepri
Villa Margherita
Unique independent accommodation with WIFI, private pool, TV, patio, pets allowed and panoramic view
- 4
- 2
- 2
Description
Charming independent villa with private swimming-pool situated in panoramic location, on the hills around the beautiful medieval town of Cortona, approx. 750 m above sea level. This property is surrounded by beautiful woods and offers tastefully furnished interiors and a cosy atmosphere. The location is ideal to enjoy the peace of the Tuscan landscape and at the same time to visit the most important historical cities of the area.
The access to the property is via an unpaved but well-maintained road.
Distances: the small village of Portole with food shops 6 km away, Cortona with al kinds of shops 13 km, Città di Castello and Arezzo approx. 40 km. Lake Trasimeno is about 30 km away.
At guests’ disposal: furnished garden, beautiful irregular-shaped swimming-pool (ca. 7 x 14 m – maximum depth 2,4 m), veranda equipped with tables and chairs for “al fresco” dining, barbecue. Use of a washing-machine and ironing facilities. Parking with the grounds.
Extra Services: Baby bed available on request. Upon request chef service available for nice Tuscan dinners.
Please carefully check if there are any extra costs to be paid on site! Villa Margherita
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 7 nights minimum and can not be combined with any other special offers.
- 5
- 2
- 1
Description
Beautiful country house situated in the heart of the renowned Chianti Classico region, approx. 20 km from Siena away. The house interiors are tastefully furnished with a charming combination of old materials and refined details. Outside guests can enjoy use of a personal, furnished, panoramic garden ideal for al-fresco dining and of a nice pool to be shared with the guests of 5 additional, nearby units.
The house's central location is convenient for visiting Tuscany's most important places of interest such as Siena, Florence, San Gimignano and the entire Chianti area with its characteristic villages (Castellina, Greve, Radda, Gaiole, etc.) and wine estates.
Distances: Villa a Sesta (a small hamlet of houses with 4 restaurants) circa 600 meters away, Castelnuovo Berardenga with shops of all kinds 7 km, Gaiole 15 km, Radda 20 km away, Castellina 30 km, Rapolano (renowned spas) 20 km away, Siena 23 km, San Gimignano 57 km away, Cortona 65 km, Florence and Arezzo 70 km away.
At guests’ disposal: personal, furnished, covered outdoor area ideal for al-fresco dining, swimming-pool (12 x 4 m – min. depth 1,2 m – max. depth 1,6 m – open from 01/05 through 30/9– from 9:00 to 19:00) to be shared with the guests of 5 additional, nearby units.
The house provides free WI-FI internet (STARLINK), wired wireless stereo system, alarm system and safe.
Personal parking in front of the house.
Additional services: Baby bed upon request. Air conditioning in the whole house (€15,-/day - payment on the spot).
Please carefully check if there are any extra costs to be paid on site! Villa Nova
Book your vacation for the period from 01 April 2026 to 31 May 2026 and save 15% (minimum 3 nights).
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 4 nights minimum and can not be combined with any other special offers.
Case Sant'Anna
Wonderful independent house with A/C, WIFI, hot tub, private pool, TV, patio, close to Cortona
- 18
- 9
- 8
Description
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
Villa Noceta
Superb independent vacation home with A/C, private pool, WIFI, TV, panoramic view, close to Cortona
- 10
- 5
- 5
Description
Beautiful villa with private pool situated in Tuscany, a short distance away from the town of Castiglion Fiorentino. This vacation villa is on a hill top and offers beautiful, extensive vies over the surrounding landscape and the castle of Montecchio. Outside, guests can enjoy use of a well-groomed garden, of furnished areas ideal for al-fresco dining and of a nice private, very panoramic pool set on a higher level in respect to the villa. This villa has been completely restored and turned into a charming country accommodation offering tastefully furnished interiors.
The villa comprises a main building for 8 persons and an outbuilding situated by the pool for 2 persons (with 1 bedroom, 1 bathroom, changing room for the pool and bathroom with shower).
The house's central location is convenient for visiting Tuscany's most important places of interest such as Siena, Florence, Arezzo, Perugia San Gimignano, the entire Chianti Classico area and the Val d’Orcia region.
Distances Castiglion Fiorentino with shops of all kinds and railway station (trains to Rome, Perugia, Orvieto, Florence, Siena) 3 km away, the lovely town of Cortona 10 km, Arezzo 20 km away, Montepulciano 40 km, Rapolano Terme (spas) 50 km, Perugia 60 km away, Siena 80 km, Florence 95 km, Orvieto 100 km away, San Gimignano 120 km.
At guests’ disposal: large, fenced-in garden with private swimming-pool (12 x 5,5 m – min. depth 1,2 m – max. depth 1,9 m), furnished outdoor area ideal for al-fresco dining, barbecue.
Free WI-FI internet provided.
Parking within the grounds.
Additional Services: Baby bed and high-chair available upon request.
Pets are permitted.
Please carefully check if there are any extra costs to be paid on site! Villa Noceta
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.
Casa alla Minuccia di Villa a Sesta
Superb independent villa with pool, A/C, WIFI, TV, patio and panoramic view, close to Siena
- 4
- 2
- 3
Description
Casa Alla Minuccia Di Villa a Sesta is a beautiful holiday home (130 sq m) with WiFi internet and air conditioning. The property can accommodate up to four people comfortably in two bedrooms with three bathrooms. Casa Alla Minuccia Di Villa a Sesta is located 710 m (2323 ft) from Villa A Sesta, Italy and only 22 km (14 mi) from Siena in the tourist area "Siena And Surroundings".
The swimming-pool is to be shared with the other 6 apartments.
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property ideal 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Outdoors you will also find a patio and barbecue grill.
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: Siena 22 km (14 mi), Greve In Chianti 40 km (25 mi), Montepulciano 54 km (34 mi), Montalcino 55 km (34 mi) and Arezzo 64 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 94 km (58 mi), Viareggio 189 km (117 mi), Forte Dei Marmi 196 km (122 mi), Rome 231 km (143 mi), Venice 345 km (214 mi) and Milan 388 km (241 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) 109 km (68 mi), Pisa (psa) 143 km (89 mi), Bologna (blq) 194 km (120 mi), Roma Ciampino (cia) 240 km (149 mi) and Roma Fiumicino (fco) 252 km (157 mi).
Casa Minuccia
- 15
- 9
- 8
Description
Conveniently located 3 km (2 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 27 km (16 mi) from Arezzo. Holiday rental Villa Gelsi is a nice stone building (230 sq m) that includes private pool, air conditioning and WiFi internet. The property can sleep up to 15 people comfortably in nine bedrooms with eight bathrooms.
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property perfect for a relaxing 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 unwind at the end the day.
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 27 km (16 mi), Montepulciano 31 km (19 mi), Perugia 51 km (32 mi), Montalcino 65 km (40 mi) and Assisi 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 212 km (131 mi), Rome 211 km (131 mi), Milan 405 km (251 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) 123 km (76 mi), Pisa (psa) 186 km (115 mi), Bologna (blq) 210 km (130 mi), Roma Ciampino (cia) 220 km (136 mi) and Roma Fiumicino (fco) 232 km (144 mi).
Villa Gelsi
Villa i Cocciai
Wonderful private accommodation with private pool, A/C, WIFI, TV, terrace and panoramic view
- 8
- 4
- 4
Description
Villa i Cocciai is located in Cortona, Italy and only 29 km (18 mi) from Arezzo in the tourist area "Cortona And Surroundings". Vacation rental Villa i Cocciai is a beautiful stone building (185 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with four bathrooms.
What to Expect
When you arrive at Villa i Cocciai you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax 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 terrace where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Montepulciano 30 km (18 mi), Perugia 52 km (32 mi), Montalcino 64 km (40 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 222 km (138 mi), Rome 210 km (130 mi), Venice 371 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 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) 187 km (116 mi), Bologna (blq) 211 km (131 mi), Roma Ciampino (cia) 218 km (135 mi) and Roma Fiumicino (fco) 231 km (143 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques required 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 discovering the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - A babysitter can be scheduled at Villa i Cocciai. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa i Cocciai
Casa Cristina
Wonderful independent vacation rental with private pool, WIFI, TV, terrace and panoramic view
- 4
- 1
- 1
Description
Holiday rental Casa Cristina is a nice property that includes WiFi internet and private pool. The property can accommodate up to four guests comfortably. Conveniently located 7 km (4 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 34 km (21 mi) from Arezzo.
Casa Cristina is the annex of a larger villa where the owners live, but at the same time it's totally independent and exclusively for the use of guests with private garden and pool only available to occupants of the cottage.
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 and the mountains perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of sightseeing. 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 four people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the ideal setting to enjoy food, family and the nice Tuscan weather.
Places Nearby
Most people enjoy visiting 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 34 km (21 mi), Montepulciano 37 km (23 mi), Perugia 59 km (37 mi), Montalcino 71 km (44 mi) and Gubbio 75 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 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
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 (138 mi), Roma Ciampino (cia) 226 km (140 mi) and Roma Fiumicino (fco) 238 km (148 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed 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 learning the secrets required to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service after arriving.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Casa Cristina
Casa i Pini
Pretty private villa rental with A/C, WIFI, private pool, TV, pets allowed and panoramic view
- 8
- 4
- 4
Description
Casa i Pini is located 7 km (4 mi) from Cortona, Italy and only 29 km (18 mi) from Montepulciano in the tourist area "Cortona And Surroundings". Casa i Pini is a beautiful stone building (180 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to eight people comfortably in four bedrooms with four bathrooms.
The accommodation consists of a main building and an annex and can accommodate up to 8 people: 6 in the main house (180 sq m) and 2 in the annex (50 square meters).
What to Expect
Upon arrival at Casa i Pini you’ll find a nice clean well-maintained property with views of the hills ideal for a peaceful 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 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 and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
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 29 km (18 mi), Arezzo 32 km (20 mi), Perugia 54 km (34 mi), Montalcino 58 km (36 mi) and Siena 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 122 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 204 km (127 mi), Venice 361 km (224 mi) and Milan 406 km (252 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Casa i Pini. 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 April - 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) 127 km (79 mi), Pisa (psa) 190 km (118 mi), Roma Ciampino (cia) 213 km (132 mi), Bologna (blq) 214 km (133 mi) and Roma Fiumicino (fco) 225 km (140 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while learning the techniques vital to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary 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 upon arrival or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - A babysitter can be scheduled at Casa i Pini. If you're traveling with kids and would like some alone time, speak to the owner directly about this option upon arrival.
Casa i Pini
Villa Oleandro
Pretty private vacation rental with private pool, WIFI, TV, terrace, pets allowed, panoramic view
- 7
- 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
Tenuta Pomona
Superb independent villa rental with WIFI, A/C, private pool, TV, patio and panoramic view
- 8
- 4
- 3
Description
Property Tenuta Pomona is a nice stone building (189 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms. Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 28 km (18 mi) from Arezzo.
The accommodation consists of the main villa in stone, which can comfortably accommodate up to 6 people and a dependance, where 2 additional guests can stay.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the city and the hills ideal for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can relax 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 coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 28 km (18 mi), Montepulciano 33 km (20 mi), Perugia 55 km (34 mi), Montalcino 67 km (42 mi) and Assisi 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (74 mi), Viareggio 205 km (127 mi), Forte Dei Marmi 212 km (132 mi), Rome 213 km (132 mi), Venice 362 km (225 mi) and Milan 405 km (251 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 186 km (116 mi), Bologna (blq) 210 km (131 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 232 km (144 mi).
More Services
Tours - The owner can organize 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.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Tenuta Pomona. Ask for more details, including the extra cost and how to arrange this service.
Baby Sitting - A babysitter can be organized at Tenuta Pomona. If you're traveling with kids and would like some alone time, talk to the owner directly about this option when you arrive.
Tenuta Pomona
Orangerie degli Ulivi
Unique private villa with A/C, WIFI, private pool, terrace, pets allowed, panoramic view
- 4
- 2
- 1
Description
Conveniently located in Cortona, Italy in the tourist area "Cortona And Surroundings" and only 29 km (18 mi) from Arezzo. Vacation rental Orangerie Degli Ulivi is a lovely stone building (60 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to four people comfortably in two bedrooms with one bathroom.
The owner lives on the property, but both the pool and the garden are for the guests' exclusive use; only the parking space is to be shared.
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid vacation 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 visiting museums. 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 four people. If you prefer to dine 'al fresco', there is a fully furnished terrace 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: Arezzo 29 km (18 mi), Montepulciano 31 km (19 mi), Perugia 52 km (33 mi), Montalcino 66 km (41 mi) and Gubbio 71 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 206 km (128 mi), Forte Dei Marmi 213 km (132 mi), Rome 211 km (131 mi), Venice 359 km (223 mi) and Milan 404 km (251 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Orangerie Degli Ulivi. 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: 1 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 125 km (77 mi), Pisa (psa) 187 km (116 mi), Bologna (blq) 211 km (131 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a pleasant 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 holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
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.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Orangerie Degli Ulivi. Ask for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be arranged at Orangerie Degli Ulivi. If you're traveling with kids and would like some alone time, talk to the owner directly about this option upon arrival.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Orangerie Degli Ulivi
La Montanina
Fabulous private vacation rental with private pool, A/C, WIFI, TV, veranda and panoramic view
- 4
- 2
- 2
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
Villa Il Sasso
Beautiful independent vacation home with private pool, A/C, WIFI, TV, terrace and panoramic view
- 13
- 7
- 5
Description
Villa Il Sasso is located in Cortona, Italy and only 29 km (18 mi) from Montepulciano in the tourist area "Cortona And Surroundings". Vacation rental Villa Il Sasso is a beautiful stone building (450 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to 13 people comfortably in seven bedrooms with five bathrooms.
Your Experience
Upon arrival at Villa Il Sasso you’ll find a lovely clean well-maintained property with views of the hills and the city ideal for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. 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 13 people. If you prefer to dine 'al fresco', there is a fully furnished terrace where you can enjoy the weather while dining outdoors.
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: Montepulciano 29 km (18 mi), Arezzo 30 km (18 mi), Perugia 51 km (32 mi), Montalcino 63 km (39 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 127 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 221 km (137 mi), Rome 209 km (130 mi), Venice 370 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 30 April - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 135 km (84 mi), Pisa (psa) 195 km (121 mi), Roma Ciampino (cia) 218 km (136 mi), Bologna (blq) 219 km (136 mi) and Roma Fiumicino (fco) 231 km (143 mi).
More Services
Tours - The owner can schedule 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.
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 when you arrive.
Villa Il Sasso
- 7
- 4
- 2
Description
Villa Elena is located 15 km (9 mi) from Cortona, Italy and only 19 km (12 mi) from Montepulciano. Vacation rental Villa Elena is a nice property (120 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to seven people comfortably in four bedrooms with two bathrooms.
What to Expect
When you arrive you’ll find a nice clean well-maintained property with views of the hills perfect 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. Also available outdoors are a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to seven people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
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 19 km (12 mi), Perugia 49 km (30 mi), Arezzo 53 km (33 mi), Montalcino 55 km (34 mi) and Assisi 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 212 km (132 mi), Forte Dei Marmi 219 km (136 mi), Rome 207 km (129 mi), Milan 412 km (256 mi) and Naples 398 km (247 mi).
Additional Information
Pool Open: 1 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 130 km (81 mi), Pisa (psa) 193 km (120 mi), Roma Ciampino (cia) 216 km (134 mi), Bologna (blq) 217 km (135 mi) and Roma Fiumicino (fco) 229 km (142 mi).
More Services
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Elena
Book your vacation for the period from 04 April 2026 to 30 May 2026 and save 10% (minimum 7 nights). Offer valid until 30 May 2026.
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.
