Le Caselle Villas with Pool
Results 281 - 300 of 414
Villa Badiuzza
Beautiful private holiday rental with private pool, WIFI, TV and patio, close to Florence
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Description
Villa Badiuzza is located 3 km (2 mi) from Moriano, Italy and only 24 km (15 mi) from Florence in the tourist area "Florence And Surroundings". Vacation rental Villa Badiuzza is a beautiful stone building (500 sq m) that includes private pool and WiFi internet. The property can accommodate up to 16 people comfortably in eight bedrooms with eight bathrooms.
What to Expect
When you arrive at Villa Badiuzza you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of shopping. Also available outdoors are a barbecue grill and patio.
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: Florence 24 km (15 mi), Greve In Chianti 32 km (20 mi), Arezzo 64 km (40 mi), San Gimignano 67 km (42 mi) and Siena 87 km (54 mi).
Some other major tourist destinations you should consider visiting are: Florence 24 km (15 mi), Viareggio 124 km (77 mi), Forte Dei Marmi 131 km (82 mi), Rome 268 km (166 mi), Milan 324 km (201 mi) and Naples 459 km (285 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 43 km (27 mi), Pisa (psa) 105 km (65 mi), Bologna (blq) 129 km (80 mi), Genova (goa) 262 km (163 mi) and Roma Ciampino (cia) 277 km (172 mi).
Villa Moriana
Casa della Selce
Amazing property with WIFI, private pool, TV, pets allowed, panoramic view, close to Montepulciano
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Description
Conveniently located in Foiano Della Chiana, Italy in the tourist area "Cortona And Surroundings" and only 19 km (12 mi) from Montepulciano. Holiday rental Casa Della Selce is a beautiful property (120 sq m) that includes private pool and WiFi internet. The property can sleep up to 12 people comfortably.
On the upper floor is another apartment inhabited by a couple, but has its own separate entrance and they do not share any spaces with guests, except for the parking.
The Experience
When you arrive at Casa Della Selce you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 12 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: Montepulciano 19 km (12 mi), Cortona 21 km (13 mi), Arezzo 29 km (18 mi), Montalcino 47 km (29 mi) and Siena 57 km (35 mi).
Some other major tourist destinations you should consider visiting are: Florence 110 km (69 mi), Viareggio 197 km (122 mi), Forte Dei Marmi 204 km (127 mi), Rome 192 km (119 mi), Venice 350 km (217 mi) and Milan 395 km (245 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Casa Della Selce. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 14:00 - 21:00
Check-Out Time: 09:00 - 11:00
Pool Open: 1 May - 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) 116 km (72 mi), Pisa (psa) 178 km (111 mi), Bologna (blq) 202 km (126 mi), Roma Ciampino (cia) 203 km (126 mi) and Roma Fiumicino (fco) 214 km (133 mi).
Casa Belvedere
Book 20 days or less before the arrival date and receive a 7 % 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.
Chiara House in Galenda, Chianti, Pool and Nature
Wonderful house with pool, WIFI, TV, terrace and panoramic view, close to Greve In Chianti
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Description
Holiday home Chiara House In Galenda, Chianti, Pool And Nature is a lovely property (90 sq m) that includes WiFi internet. The property can sleep up to six guests comfortably in two bedrooms with one bathroom. Conveniently located 13 km (8 mi) from Gaiole In Chianti, Italy in the tourist area "Siena And Surroundings" and only 24 km (15 mi) from Greve In Chianti.
Your Experience
When you arrive you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your enjoyment you will find a pool where you can relax while enjoying a nice cold beverage after a busy day of visiting museums. There is a kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to six people.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 24 km (15 mi), Siena 29 km (18 mi), San Gimignano 44 km (28 mi), Florence 56 km (35 mi) and Montalcino 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 56 km (35 mi), Viareggio 150 km (93 mi), Forte Dei Marmi 157 km (98 mi), Rome 251 km (156 mi), Milan 350 km (217 mi) and Naples 442 km (275 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 69 km (43 mi), Pisa (psa) 115 km (72 mi), Bologna (blq) 155 km (96 mi), Roma Ciampino (cia) 260 km (162 mi) and Roma Fiumicino (fco) 273 km (169 mi).
The swimming pool is shared with four apartments in the village. Chiara House In Galenda, Chianti, Pool And Nature
Book your vacation for the period from 10 April 2027 to 15 November 2027 and save 15% (minimum 5 nights).
Book your vacation for the period from 10 April 2027 to 15 November 2027 and save 25% (minimum 7 nights).
Villa Lucolena
Amazing private villa rental with WIFI, private pool, TV and panoramic view, near Greve In Chianti
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Description
Welcoming villa with private swimming pool in the heart of Chianti. The property is surrounded by farming estates and rolling hills, turning this area in one of the most sought after of Tuscany. From the terrace of this villa rental in Chianti, guests can enjoy panoramic views over the surrounding countryside. The town of Figline Valdarno is just 14km away and is provided with a train station with regular connections to Florence and Arezzo.
Inside, this villa rental is welcoming and perfect for families or small groups of friends.
The guests staying in Villa Lucolena have access to: private swimming pool: 14m x 7m; minimum depth: 1,3m; maximum depth: 2,5m., private garden, wi-fi internet connection (free wi-fi), panoramic terrace furnished for al-fresco dining, barbecue,, marble bathrooms, washing machine, parking
Distances: Lucolena (with food shop) just a few steps away, Greve in Chianti (shops of any kind) 13 km away, Figline Valdarno 14 km away, Florence 35 km away, Siena 45 km away, San Gimignano 60 km away, Arezzo 65 km away, Montalcino (famous for its Brunello wine) 90 km away, Cortona 100 km away, Rome 275 km away.
Please carefully check if there are any extra costs to be paid on site! Villa Lucolena
Villa Patrizia
Superb private villa rental with private pool, hot tub, A/C, WIFI, TV, panoramic view, near Cortona
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Description
Conveniently located 600 m (1953 ft) from Sant'angiolo, Italy in the tourist area "Cortona And Surroundings" and only 3 km (2 mi) from Cortona. Holiday rental Villa Patrizia is a lovely stone building (250 sq m) that includes hot tub, air conditioning and private pool. The property can accommodate up to 12 guests comfortably in five bedrooms with four bathrooms.
Your Experience
Upon arrival you’ll find a nice clean well-maintained property with views of the hills and the mountains ideal for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of 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 12 people.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 3 km (2 mi), Arezzo 31 km (19 mi), Montepulciano 33 km (21 mi), Perugia 51 km (32 mi) and Gubbio 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 134 km (83 mi), Viareggio 220 km (137 mi), Forte Dei Marmi 228 km (141 mi), Rome 216 km (134 mi), Venice 373 km (232 mi) and Milan 418 km (260 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Patrizia. 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 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) 139 km (87 mi), Pisa (psa) 201 km (125 mi), Roma Ciampino (cia) 225 km (140 mi), Bologna (blq) 226 km (140 mi) and Roma Fiumicino (fco) 237 km (147 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be scheduled at the property. It's a fun way to spend time with friends and family while discovering the techniques needed to master Tuscan cuisine. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the additional costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the individual 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 Patrizia. Inquire for more details, including the extra cost and how to arrange this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be scheduled. Speak to the owner directly about this service after arriving.
Villa Patrizia
Fonte della Chiana
Fabulous private property with sauna, private pool, A/C, WIFI, hot tub, TV, close to Cortona
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Description
Fonte Della Chiana is a beautiful stone building (500 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to 17 people comfortably in six bedrooms with six bathrooms. Fonte Della Chiana is located 6 km (4 mi) from Foiano Della Chiana, Italy and only 21 km (13 mi) from Cortona in the tourist area "Cortona And Surroundings".
What to Expect
When you arrive 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, 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. 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 and refrigerator, as well as, plenty of tableware and cutlery for up to 17 people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the lovely Tuscan weather.
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 21 km (13 mi), Arezzo 23 km (14 mi), Montepulciano 27 km (17 mi), Montalcino 52 km (32 mi) and Siena 61 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 102 km (63 mi), Viareggio 189 km (117 mi), Forte Dei Marmi 196 km (122 mi), Rome 200 km (124 mi), Venice 345 km (215 mi) and Milan 387 km (240 mi).
Additional Information
Check-In Time: 17:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 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) 110 km (68 mi), Pisa (psa) 170 km (106 mi), Bologna (blq) 194 km (121 mi), Roma Ciampino (cia) 209 km (130 mi) and Roma Fiumicino (fco) 222 km (138 mi).
Villa Ripa
Villa Giare
Superb private villa with private pool, hot tub, A/C, WIFI and panoramic view, close to Cortona
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Description
Beautiful and charming ancient property situated in quiet and panoramic location in the hills surrounding Cortona. This property has been recently restored with its ancient architectural features preserved and converted into 8 appealing apartments, all of which offer tastefully furnished interiors that allow their guests a combination of old charm and contemporary design.
Splendid extensive views of the surrounding valleys.
From the park and from the apartments you can enjoy a magnificent view surrounding hills.
The garden well kept and maintained, has a gazebo ideal for outdoor living and al fresco dining.
At guests' disposal:
By renting the 8 apartments together it is possible to obtain an independent villa with private swimming-pool. Common room with dining room with fireplace, kitchen, 2 toilets.
Baby bed available free of charge. Barbecue.
The swimming pool, 14 x 7 depth 1.40 offers a splendid view over the valley. Wi-Fi internet connection available free of charge. Mosquito screens in all the units. Parking within the grounds
Distances:
The village of Fratticciola is at only 200 mt with a food shop.
Fratta at 2 km with shops and restaurant.
Camucia at 5 km
Cortona at 8 km
Note: The villa has an outdoor video surveillance system
Please carefully check if there are any extra costs to be paid on site! Villa Giare
Book your vacation for the period from 09 April 2026 to 01 November 2026 and save 5% (minimum 4 nights). Offer valid until 30 April 2026.
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.
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Description
Property Summary
Montefienali is a historical holiday village located 15 km from Gaiole in Chianti, Italy, nestled in the countryside at an elevation of 600 meters above sea level. This renovated 13th-century property offers 25 apartments within a hamlet of 25 houses. Guests can enjoy a natural state property spanning 3 hectares with plants, trees, and a seasonal swimming pool (10 x 15 m) available from May 15 to September 30, with pool opening hours from 9:00 AM to 8:00 PM. The property boasts amenities such as a children's pool, outdoor shower, patio, terrace, garden furniture, and a children's playground with a slide, swing, and sandbox. Laundry facilities (shared) are available on-site. While the property is accessible via a 2 km bumpy motor access road, it offers parking on the premises and is within proximity to shops, groceries, supermarkets, restaurants, bars, and bicycle rentals, making it an ideal vacation rental for families seeking a peaceful retreat in the Tuscan countryside.
Outdoors
Immerse yourself in the natural beauty of Montefienali, surrounded by trees on a fenced 3-hectare property. Soak up the sun by the seasonal swimming pool (10 x 15 m), available from May 15 to September 30, with designated pool opening hours from 9:00 AM to 8:00 PM. Children can make a splash in the dedicated children's pool or enjoy the outdoor playground with a slide, swing, and sandbox. Relax on the patio or terrace, surrounded by lush gardens and equipped with comfortable garden furniture. Outdoor showers are also available for your convenience.
Other Information
Montefienali offers convenient on-site amenities, including a shared washing machine for laundry needs. While the property is situated in a secluded location, it is easily accessible via a 2 km bumpy motor access road, with parking available on the premises. A 50-meter footpath leads from the parking area to the accommodations. The property caters to families, with baby equipment provided. Please note that groups of teenagers are accepted upon request only.
Distances and Attractions
Nestled in the Tuscan countryside, Montefienali is conveniently located near various attractions and amenities. The charming town of Gaiole in Chianti is just 15 km away, offering shops, groceries, and a supermarket. Restaurants and bars can be found within a 3 km radius, while bicycle rentals are available 15 km from the property. Explore the rich history and culture of nearby cities such as Siena (36 km), Arezzo (44 km), and Florence (66 km), all within a reasonable driving distance from your vacation rental. Il Cinghiale
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| Accommodation | |||||
|---|---|---|---|---|---|
| San Regolo 915.1 | 2 | 1 | 1 | ||
| San Regolo 915.2 | 4 | 2 | 2 | ||
| All 2 Accommodations | 6 | 3 | 3 |
Description
Property Summary
Villa San Regolo is a stunning vacation rental located in the picturesque hamlet of San Regolo, just 10 km from the charming town of Gaiole In Chianti, Italy. This resort boasts 6 houses, offering guests a serene and peaceful escape. The property is equipped with a range of amenities, including a swimming pool, internet WiFi, parking facilities, an EV charging station, and the option for an installment plan.
Outdoors
Immerse yourself in the beauty of the Tuscan countryside at Villa San Regolo. The resort features a shared swimming pool (15 x 6 m, with a depth ranging from 120 to 220 cm) available seasonally from May 1st to October 25th. Guests can also enjoy a children's pool, an outdoor shower, and a beautifully maintained garden with furniture, tended to by the owner/gardener.
Other Information
Villa San Regolo offers a range of additional services and facilities to enhance your stay. The complex features a reception area, and guests can indulge in relaxing massages (at an extra cost). Central heating is available, along with laundry facilities, including a shared washing machine. Heating costs are payable on-site (from March 29th to October 31st) and is available from November 1st to March 28th. Bicycles (6) are available for rent (extra charge), and a cook can be arranged upon request (additional cost). Parking is provided on the premises, and an e-charging station is available for electric vehicles.
Distances and Attractions
Villa San Regolo is conveniently located near several attractions and points of interest. The Castello di Brolio is just 2 km away, while Castelnuovo Berardenga is 13 km from the resort. The historic city of Siena is a 20 km drive, and Castellina in Chianti is 27 km away. Other nearby destinations include Greve in Chianti (35 km), Monteriggioni (35 km), and Monte San Savino (39 km). For those seeking a beach getaway, the sandy shores of Castiglione della Pescaia are 115 km from the resort, and the thermal baths of Rapolano Terme are just 26 km away. Gaiole in Chianti 915
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Description
If you have imagined your holiday immersed in the Tuscan countryside, if your dream is to wake up in the morning, open the windows and find yourself surrounded by golden sunflowers and ears of corn, Il Viaggiolo is the house for you. From your windows, from the garden, from the swimming pool you will have, as far as the eye can see, cultivated fields, vineyards, olive groves and rolling hills that change colour with the seasons.
Here and there are ancient villages rich in history and tradition. One of these is Marciano della Chiana (3 km), dominated by its castle, over which the mighty tower stands like a grim sentinel, majestically overlooking the valley below. You could do your shopping in grocery stores and supermarkets in Foiano della Chiana, also about 3 km away.
Il Viaggiolo is an old farmhouse that in recent years has regained its original beauty. The wooden beams, the warm colours used and the stylish furniture give it a cosy and comfortable atmosphere that will make you feel immediately comfortable and welcome. The farmhouse will be the ideal place for your family holidays, the outdoor space, large and safe, will allow your children to run and explore while you enjoy an aperitif by the pool. Or even if you are travelling in a group, Il Viaggiolo will provide you with large and comfortable space for dinners with your friends, or it can also serve as a starting point for your trips to discover the villages and cities of art in central Italy.
The farmhouse is surrounded by a large garden shaded by tall trees, decorated with pots and flowers and equipped with table, chairs, umbrellas, swing and barbecue. Under the large centuries-old oak tree, to the side of the house, there is a small corner designed for relaxing with a good book or for an evening chat with friends and a glass of wine. The beautiful 5 x 10 m swimming pool (depth 1.40 m - open from 01st May to 30th September), for your exclusive use, has sunbeds and umbrellas and a comfortable bathroom with shower. Two covered parking spaces are also available.
Something we are sure you will not forget about your holiday at Viaggiolo is the kindness and courtesy of the owners, who will spoil and pamper you in every possible way. Il Viaggiolo
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Description
Santa Vittoria is located on the first floor of a typical farmhouse in a panoramic position on top of a hill covered with vineyards and olive groves. It is part of an important farm producing excellent wine and fine extra virgin olive oil, which you can taste and buy.
From the windows of the old farmhouse, you will enjoy an incomparable view of the suggestive landscape of the Valdichiana hills, where, scattered here and there, you will glimpse beautiful farmhouses, 19th-century villas and medieval villages dominated by mighty castles. An idyllic setting that will be nourishment for both your eyes and your mind.
Santa Vittoria is an old house with a special appeal. The wooden ceilings, the floors all in Tuscan terracotta and the original period furnishings give it a very rustic and characteristic charm. You will experience your stay in an atmosphere of old, simple and essential things.
On the ground floor of the farmhouse lives, occasionally, the property caretaker who will be a discreet point of reference in case of need.
You will have at your disposal, in front of the house, a large green area equipped with a pergola and garden furniture, perfect for your evenings in the open air. About 250 metres away, near another farmhouse that is also part of the farm, you will find the laundry room and the swimming pool area (size 7x12 m, depth 1.20 - 1.80 - open from 01st May to 30th September) that you can use together with the owner and his guests.
Santa Vittoria is a country house that you will remember, not only for its location, but also for the sensations that a holiday spent here will leave you. Santa Vittoria
Gaiole in Chianti 649
Pretty multi-unit villa with WIFI, private pool, A/C, TV, terrace, pets allowed and panoramic view
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| Accommodation | |||||
|---|---|---|---|---|---|
| Montechioccioli 649.1 | 6 | 2 | 1 | ||
| Montechioccioli 649.2 | 6 | 2 | 1 | ||
| All 2 Accommodations | 12 | 4 | 2 |
Description
Property Summary
Nestled in the picturesque hamlet of Rietine, just 4 km from the centre of Gaiole in Chianti, Italy, Montechioccioli is a charming 3-family house that offers an authentic and rustic holiday rental experience in the heart of Tuscany. Surrounded by rolling vineyards and breathtaking countryside, this property comprises 3 separate apartments, making it an ideal choice for families or groups of friends seeking to immerse themselves in the beauty of the Tuscan landscape. The property features a generous terraced yard spanning 1,000 m2, beautifully landscaped with a variety of plants and trees that frame the surrounding scenery. Guests can take a refreshing dip in the impressive swimming pool, which measures 12 x 6 m with a depth of 170 cm and is available seasonally from 02 May to 03 October. Staying connected is effortless thanks to the internet wifi available throughout the property, while an EV charging station further enhances the convenience and modernity of this countryside retreat. A washing machine is also available for shared use among guests, and parking is provided on the premises.
Outdoors
The outdoor spaces at Montechioccioli are a true highlight of the property, offering guests a wonderful setting in which to unwind and enjoy the Tuscan countryside. The terraced garden, extending across 1,000 m2, is thoughtfully planted with a diverse selection of trees and plants, creating a lush and tranquil environment that invites relaxation at every turn. The swimming pool area, where the pool reaches a depth of 170 cm, is complemented by a dedicated shower and WC facility, ensuring comfort and practicality for all guests. Adjacent to the pool, a terrace equipped with a barbecue provides an ideal space for outdoor dining and socialising, allowing guests to savour al fresco meals while taking in the panoramic views of the surrounding vineyards and hills.
Other Information
The owner of Montechioccioli resides on the same property, ensuring a welcoming and attentive presence throughout your stay. The swimming pool is available on a seasonal basis, open from 02 May to 03 October. A washing machine is available on the premises and is shared among the guests of the 3 apartments. Parking is conveniently provided on site at no additional inconvenience to guests.
Distances and Attractions
Montechioccioli enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations. The centre of Gaiole in Chianti is just 4 km away, offering a charming selection of local restaurants, shops, and services that capture the essence of authentic Chiantishire life. The historic town of Radda in Chianti lies approximately 12 km from the property, providing further opportunities to explore the region's renowned wine culture, medieval architecture, and traditional Tuscan cuisine. For those wishing to venture further afield, the magnificent city of Siena, a UNESCO World Heritage Site famed for its Gothic cathedral and the legendary Piazza del Campo, is located approximately 40 km from the property and makes for an unforgettable day trip. Gaiole in Chianti 649
Special Offer for Montechioccioli 649.1
Apartment:
Montechioccioli 649.2
Last-Minute Offer for Montechioccioli 649.1
Other apartments with last-minute offers:
Montechioccioli 649.2
Villa Michelangelo
House with WIFI, private pool, A/C, hot tub, TV, balcony, panoramic view, near Cortona
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Description
Property Summary
Nestled on a gentle hill in the heart of Foiano Della Chiana, Italy, Villa Michelangelo is a remarkable holiday retreat that invites you to experience the timeless beauty of the Tuscan countryside. From its elevated position, the property offers breathtaking, seemingly infinite views stretching across rolling landscapes adorned with ancient olive groves, traditional wineries, and vibrant wildflowers. The villa provides a generous outdoor yard that perfectly frames the surrounding natural scenery, creating an atmosphere of serene elegance. A private swimming pool allows you to cool off while soaking in the panoramic vistas that define this extraordinary corner of Tuscany. Seamless connectivity is ensured through reliable Internet Wifi, keeping you comfortably in touch with the world beyond, while dedicated parking on the premises offers the convenience and peace of mind you deserve throughout your stay.
Outdoors
The outdoor spaces of Villa Michelangelo are a true celebration of the Tuscan landscape. The private swimming pool serves as the centrepiece of the exterior, perfectly positioned to allow you to enjoy the sweeping views of the countryside while you relax and unwind. The surrounding yard extends gracefully across the hillside, offering generous open spaces where the natural beauty of the olive groves and flowering gardens becomes an integral part of your daily experience. Whether you choose to dine al fresco, lounge in the warmth of the Tuscan sun, or simply take in the tranquil panorama that unfolds before you, the outdoor areas of the villa provide an idyllic setting for every moment of your stay.
Other Information
Villa Michelangelo is thoughtfully designed to ensure a comfortable and seamless experience for all guests. The property's hillside position near Arezzo provides a peaceful and private environment, making it an ideal base from which to explore the wider region. The surrounding landscape of olive groves and wineries adds an authentic Tuscan character to the setting, enhancing the overall atmosphere of the retreat.
Distances and Attractions
Villa Michelangelo's privileged location near Arezzo places you within easy reach of some of the most celebrated destinations in all of Italy. The property serves as an excellent base for day trips throughout Tuscany, allowing you to explore the Renaissance splendour of Florence, the medieval charm of Siena, and the enchanting hilltop town of Cortona. The spiritual city of Assisi, the renowned wine town of Montepulciano, and the celebrated Chianti wine region are all comfortably accessible, offering an extraordinary variety of cultural, historical, and gastronomic experiences. Whether you are drawn to world-class art, ancient architecture, or the celebrated flavours of Tuscan cuisine, the surrounding region promises an abundance of unforgettable discoveries just a short drive from the villa. Villa Michelangelo
Villa Ripa
Accommodation with WIFI, A/C, hot tub, private pool, TV, patio, panoramic view, close to Cortona
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Description
Property Summary
Nestled within 3 hectares of a beautifully maintained natural park adorned with cypress trees, lavender, and roses, Villa la Ripa is an exclusive luxury holiday retreat situated in the heart of Tuscany, Italy. Recently fully renovated, this remarkable property in Foiano Della Chiana seamlessly blends traditional character with contemporary elegance across approximately 800 square metres of interior space. Guests enjoy complimentary Wi-Fi throughout the villa, a private swimming pool measuring 12x4 metres equipped with sun loungers and umbrellas, extensive parking facilities, and a sweeping private yard that creates an atmosphere of complete seclusion and natural beauty.
Outdoors
The expansive private park surrounding the villa provides an extraordinary outdoor experience. A covered built-in patio furnished with a large dining table, chairs, a barbecue, and a pizza oven offers the ideal setting for al fresco meals immersed in nature. At the heart of the park, a glass-walled gym room allows guests to exercise while feeling entirely surrounded by the natural landscape. A soccer field and volleyball court further enrich the outdoor offering, while the pool area invites relaxation in a serene and picturesque environment.
Distances and Attractions
Villa la Ripa is set in the Arezzo countryside, accessed via a characteristic cypress-lined country road. The nearest town, Foiano Della Chiana, is just 6 km away and provides all essential services. Cortona is 20 km distant, Arezzo 25 km, Montepulciano 27 km, and Siena 57 km. Florence Airport is approximately 100 km away, Pisa Airport 166 km, and Rome Airport 223 km. The location is ideal for day trips to Tuscany's most celebrated destinations, including Florence, Arezzo, Siena, Cortona, and the Chianti wine region.
Unit Layout
Villa la Ripa accommodates up to 16 guests across 6 bedrooms and 8 bathrooms, divided between a main building and a separate dependence. The main building spans 3 floors. The ground floor features a large living area with elegant sofas, a dining room, a fully equipped kitchen, and 1 full bathroom. The first floor hosts 5 double bedrooms, each with its own en-suite shower room and minibar fridge; 1 bedroom can be converted into twin beds upon request, and 2 bedrooms can each accommodate an additional single bed. All rooms overlook the park. The basement includes a second kitchen, a spacious open-plan area for activities such as wine tasting and cooking classes, a cellar stocked with fine Tuscan wines including Montalcino, Montepulciano, and Chianti, a living area with sofas, and a billiard table. The basement also houses the spa, featuring a jacuzzi bath, relaxation lounges, a sauna, a Turkish bath, an emotional shower, and changing and massage rooms. The dependence offers a ground-floor kitchen, a living area with a double sofa bed, and a first-floor double bedroom with a private bathroom and walk-in wardrobe.
Amenities Included
The villa is fully equipped with air conditioning and heating available throughout. Each bedroom benefits from individual climate control, while a washing machine is available in the dedicated laundry room. The kitchen is fitted with a dishwasher and microwave among its full complement of appliances. Guests can enjoy the barbecue on the private patio, which serves as a wonderful outdoor entertaining space. Every room is connected to the BOSE music system, controllable via smartphone, and entertainment is provided through satellite television with Netflix included, as well as additional television sets throughout the property. The fireplace in the main living area adds warmth and elegance during cooler evenings. The jacuzzi bathtub within the spa completes an exceptional wellness offering. An alarm system, fire extinguisher, first aid kit, air purification system, and courtesy amenities in each bathroom are also provided.
Other Information
The minimum rental period is 1 week, with Saturday as the changeover day. Check-in is available from 4:00 pm to 7:00 pm, and check-out must be completed before 10:00 am. A refundable security deposit of 1500 euros is payable in cash upon arrival and returned at departure, less any damages or unpaid fees. A tourist tax of 2.50 euros per person per night applies. Use of the spa is available at an additional cost of 400 euros per day. The rental price includes final cleaning, air conditioning and heating, gym access, and pool towels. An emergency contact is provided at check-in, and the team is available to assist with excursions, wine tours, cooking experiences, and further activities throughout the stay. Villa Ripa
Villa Chicco
Private Villa with WIFI, private pool, TV, patio, panoramic view, close to Greve In Chianti
- 5
- 2
- 1
Description
Villa Chicco is located in the centre of Dimezzano, Italy and only 15 km (9 mi) from Greve In Chianti in the tourist area "Chianti". Vacation rental Villa Chicco is a nice stone building (102 sq m) that includes WiFi internet and private pool. The property can sleep up to five guests comfortably in two bedrooms with one bathroom.
What to Expect
Upon arrival you’ll find a beautiful clean well-maintained property with views of the hills 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 hectic day of visiting museums. 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, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to five people.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 15 km (9 mi), Florence 37 km (23 mi), Siena 47 km (29 mi), San Gimignano 53 km (33 mi) and Arezzo 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 37 km (23 mi), Viareggio 146 km (91 mi), Forte Dei Marmi 153 km (95 mi), Rome 272 km (169 mi), Milan 346 km (215 mi) and Naples 463 km (288 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) 64 km (40 mi), Pisa (psa) 127 km (79 mi), Bologna (blq) 151 km (94 mi), Roma Ciampino (cia) 281 km (175 mi) and Genova (goa) 287 km (178 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques vital to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a 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 extra cost, please contact us.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Villa Chicco. Ask for more details, including the supplemental cost and how to organize this service.
The garden is fully enclosed.
Up to 2 dogs are permitted.
Villa Chicco
Book your vacation for the period from 06 September 2024 to 31 December 2027 and save 5% (minimum 7 nights).
Book your vacation for the period from 06 September 2024 to 31 December 2027 and save 10% (minimum 14 nights).
Book 15 days or less before the arrival date and receive a 5 % 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.
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
Conveniently located 710 m (2323 ft) from Villa A Sesta, Italy in the tourist area "Siena And Surroundings" and only 22 km (14 mi) from Siena. 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 guests comfortably in two bedrooms with three bathrooms.
The swimming-pool is to be shared with the other 6 apartments.
Your Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property perfect for a splendid 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. For your pleasure, on the grounds there is a barbecue grill and patio.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: 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
Villa Gelsomino
Independent Vacation home with WIFI, A/C, private pool, TV, patio, panoramic view, near Cortona
- 8
- 4
- 3
Description
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
- 4
- 2
- 3
Description
Comfortable country house in the hills of the renowned Chianti Classico area, about 20 km from Siena. The interiors are tastefully furnished using characteristic Tuscan materials. Outside, there is a private, furnished area where you can eat outdoors and enjoy views of the surrounding landscape. A beautiful pool is just a few meters away and is shared with the guests of the other units.
This property is strategically located right in the middle of the Chianti Classico production area, where there are numerous wineries for wine tasting. In the area there are also many castles (Brolio, Meleto, Bossi . . .) and medieval country churches.
At guests' disposal: private, covered outdoor space with dining area; completely enclosed pool area that is shared with the guests of the 5 adjacent units (12 x 4 m - minimum depth 0,5 m - maximum depth 1,5 m -open 01/05 to 30/9 - can be used from 9:00 to 19:00); Wifi internet; parking outside the grounds; barbecue; garden; air conditioning in the bedrooms
At the disposal of Casa Minuccia guests: Distances: Villa a Sesta (small hamlet with 4 restaurants) about 600 meters away, Castelnuovo Berardenga with shops of all kinds 7 km, Gaiole 15 km, Radda 20 km, Castellina 30 km, Rapolano (renowned thermal spas) 20 km, Siena 23 km, San Gimignano 57 km, Cortona 65 km, Florence and Arezzo 70 km.
Please check carefully for any extras that must be paid at the property! Casa Minuccia
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.
Villa Il Borgo
Private Holiday villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Cortona
- 8
- 4
- 4
Description
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
