Guistrigona Villas with Pool
Results 101 - 120 of 401
Villa sulle Crete
Fabulous independent holiday home with WIFI, A/C, private pool, hot tub and balcony
- 20
- 9
- 9
Description
Villa Sulle Crete is located 6 km (4 mi) from Trequanda, Italy and only 26 km (16 mi) from Montepulciano in the tourist area "Orcia Valley". Villa Sulle Crete is a nice stone building (910 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to 20 guests comfortably in nine bedrooms with nine bathrooms.
What to Expect
When you arrive you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. After a busy day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. 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 holiday. The kitchen includes coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to 20 people. Dine 'al fresco' like a real Tuscan, the fully furnished balcony is the perfect setting to enjoy food, family and the lovely 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: Montepulciano 26 km (16 mi), Montalcino 28 km (18 mi), Siena 40 km (25 mi), Cortona 45 km (28 mi) and Arezzo 48 km (30 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (139 mi), Rome 211 km (131 mi), Venice 369 km (229 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 17:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 25 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) 135 km (84 mi), Pisa (psa) 197 km (122 mi), Roma Ciampino (cia) 220 km (137 mi), Bologna (blq) 221 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Villa Asciano 20
- 4
- 21
- 8
- 4
| Accommodation | |||||
|---|---|---|---|---|---|
| Girasole 801.1 | 4 | 1 | 1 | ||
| Lavanda 801.2 | 6 | 3 | 1 | ||
| Rosmarino 801.3 | 5 | 2 | 1 | ||
| Corbezzolo 801.4 | 6 | 2 | 1 | ||
| All 4 Accommodations | 21 | 8 | 4 |
Description
Property Summary
Manor House "Filicaia" is a beautiful vacation rental located in Cavriglia, Italy, situated at an elevation of 150 meters above sea level. The property comprises five apartments and offers a range of amenities, including a swimming pool, yard, internet WiFi, parking, and the option for an installment plan. Guests can enjoy a comfortable stay with the shared use of a washing machine and heating (charges apply from 01.11 to 07.04). The owner of the property resides on the premises.
Outdoors
The vacation rental boasts a shared swimming pool that measures 12 x 6 meters with a depth of 120-200 cm, available for seasonal use from 07.May to 24.Sep. Guests can unwind in the garden area, complete with outdoor shower facilities, garden furniture, and a barbecue area.
Other Information
The property is conveniently located just 3.8 km from the center of San Giovanni Valdarno, 18 km from the center of Gaiole in Chianti, and 26 km from the center of Radda in Chianti.
Distances and Attractions
Surrounding attractions within driving distance include the Castello di Meleto, Greve in Chianti, Castellina in Chianti, Panzano in Chianti, Firenze, and Siena. With its prime location and proximity to nearby villages and attractions, Manor House "Filicaia" offers the perfect holiday rental for exploring the Tuscan countryside. San Giovanni 801
Villa Pietrafitta
Wonderful private holiday rental with WIFI, private pool, TV and patio, near Greve In Chianti
- 12
- 6
- 6
Description
Conveniently located 5 km (3 mi) from Castellina In Chianti, Italy in the tourist area "Siena And Surroundings" and only 17 km (11 mi) from Greve In Chianti. Holiday home Villa Pietrafitta is a nice stone building (200 sq m) that includes private pool and WiFi internet. The property can sleep up to 12 guests comfortably in six bedrooms with six bathrooms.
What to Expect
Upon arrival you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid vacation in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, 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. Outside you will also find a barbecue grill and patio. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished patio is the perfect setting to enjoy food, family and the nice Tuscan weather.
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: Greve In Chianti 17 km (11 mi), Siena 26 km (16 mi), San Gimignano 33 km (20 mi), Florence 46 km (28 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 46 km (28 mi), Viareggio 140 km (87 mi), Forte Dei Marmi 147 km (91 mi), Rome 267 km (166 mi), Milan 340 km (211 mi) and Naples 458 km (284 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:00 - 10:00
Pool Open: 3 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) 59 km (36 mi), Pisa (psa) 105 km (65 mi), Bologna (blq) 145 km (90 mi), Roma Ciampino (cia) 276 km (171 mi) and Genova (goa) 278 km (173 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a enjoyable way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the 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 mouth-watering 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.
Villa Pietrafitta
Book your vacation for the period from 02 May 2026 to 30 May 2026 and save 20% (minimum 7 nights).
Book your vacation for the period from 01 August 2026 to 31 August 2026 and save 15% (minimum 7 nights).
- 6
- 2
- 2
Description
Conveniently located 2 km (1 mi) from Levane, Italy in the tourist area "Arno Valley" and only 27 km (17 mi) from Arezzo. Casina Dell'acquaborra is a beautiful stone building (140 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to six guests comfortably in two bedrooms with two bathrooms.
The First Floor of the property is empty and not accessible to guests.
The property has an automatic locking system that is activated by a switch inside the house.
Your Experience
When you arrive at Casina Dell'acquaborra you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid vacation in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. There is a kitchen including coffee machine, microwave and refrigerator, as well as, plenty of tableware and cutlery for up to six people. If you prefer to dine 'al fresco', there is a fully furnished garden 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: Arezzo 27 km (17 mi), Greve In Chianti 40 km (25 mi), Siena 50 km (31 mi), Cortona 51 km (32 mi) and Montepulciano 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 67 km (42 mi), Viareggio 151 km (94 mi), Forte Dei Marmi 161 km (100 mi), Rome 249 km (155 mi), Venice 312 km (194 mi) and Milan 356 km (221 mi).
Additional Information
Check-In Time: 15:00 - 21:00
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) 75 km (46 mi), Pisa (psa) 135 km (84 mi), Bologna (blq) 161 km (100 mi), Roma Ciampino (cia) 258 km (160 mi) and Roma Fiumicino (fco) 271 km (168 mi).
Casina Al Vento
Villa Ida
Private Vacation home with WIFI, A/C, pool, TV, patio, pets allowed, near Greve In Chianti
- 6
- 2
- 2
Description
Villa Ida is located 4 km (3 mi) from Castellina In Chianti, Italy and only 19 km (12 mi) from Greve In Chianti in the tourist area "Siena And Surroundings". Vacation rental Villa Ida is a beautiful stone building (120 sq m) that includes air conditioning and WiFi internet. The property can sleep up to six people comfortably in two bedrooms with two bathrooms.
The pool is shared with another villa for 5 people, which is only used occasionally.
Your Experience
After arriving 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 peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, 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. Outdoors you will also find a barbecue grill and patio.
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 19 km (12 mi), Siena 26 km (16 mi), San Gimignano 32 km (20 mi), Florence 48 km (30 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 48 km (30 mi), Viareggio 142 km (88 mi), Forte Dei Marmi 149 km (93 mi), Rome 266 km (165 mi), Milan 342 km (212 mi) and Naples 457 km (284 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Ida. 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) 61 km (38 mi), Pisa (psa) 107 km (66 mi), Bologna (blq) 147 km (91 mi), Roma Ciampino (cia) 275 km (171 mi) and Genova (goa) 280 km (174 mi).
A Casa Dell'ida
- 8
- 3
- 3
Description
Villa Dell'acquaborra is a nice stone building (220 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to eight people comfortably in three bedrooms with three bathrooms. Conveniently located 2 km (1 mi) from Levane, Italy in the tourist area "Arno Valley" and only 27 km (17 mi) from Arezzo.
The property has an automatic locking system that is activated by a switch inside the house.
The Experience
Upon arrival at Villa Dell'acquaborra you’ll find a lovely clean well-maintained property perfect for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of sightseeing. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 27 km (17 mi), Greve In Chianti 40 km (25 mi), Siena 50 km (31 mi), Cortona 51 km (32 mi) and Montepulciano 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 67 km (42 mi), Viareggio 154 km (96 mi), Forte Dei Marmi 161 km (100 mi), Rome 249 km (155 mi), Venice 311 km (193 mi) and Milan 352 km (219 mi).
Additional Information
Check-In Time: 15:00 - 21:00
Check-Out Time: 08:00 - 11:00
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) 73 km (45 mi), Pisa (psa) 135 km (84 mi), Bologna (blq) 159 km (99 mi), Roma Ciampino (cia) 258 km (160 mi) and Roma Fiumicino (fco) 271 km (168 mi).
Villa Al Vento
Casa Fioraie
Private Holiday home with WIFI, A/C, private pool, TV, patio, panoramic view, near Greve In Chianti
- 6
- 2
- 2
Description
Holiday home in a strategic position in Castellina in Chianti.
Casa Fioraie is the ideal place to spend a relaxing and fun holiday.
The house offers two bedrooms (with air conditioning) as well as a large outdoor area, perfect for organizing barbecues and enjoying the wonderful panoramic view of the surrounding hills. In the garden there is a beautiful private pool that allows guests to relax and cool off in the summer season.
The property, thanks to its spacious interiors and its large exteriors, guarantees a pleasure and safe stay. All the areas, including the swimming pool, are carefully sanitized and sterilized for the health and tranquility of guests.
The Chianti Classico area in which Casa Fioraie is located is one of the most renowned places in Italy and in the world for its characteristic villages, food and wine culture, splendid cities of art and breathtaking scenery.
You reach the house through a gravel road of about 500 meters in good condition but not suitable for particularly sporty vehicles.
At guests' disposal: 2 air-conditioned bedrooms, double sofa bed for 2 people, possibility of accommodating 4/6 people, panoramic private pool (10 x 4.5 meters, maximum depth: 1.60 meters, minimum depth: 1, 20 meters), barbecue, outdoor area equipped with sofas and table with chairs for outdoor dining, Wi-Fi internet connection.
Distances: a Restaurant / Bar is located at 850 meters from the house, Castellina in Chianti (all kinds of shops) at 6 km, Poggibonsi at 14 km, Radda at 18 km, San Gimignano at 25 km, Siena at 30 km, Florence at 50 km, Pienza at 85 km, Montepulciano at 95 km, Cortona at 105 km, the Tuscan coast (Cecina or Castiglioncello) is at 100 km away.
Please carefully check if there are any extra costs to be paid on site! Casa Fioraie
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 Anita - Castellina in Chianti - Granaio, Tosc
Private Holiday home with pool, WIFI, A/C, TV, veranda, panoramic view, close to San Gimignano
- 4
- 2
- 1
Description
Casa Anita - Castellina In Chianti - Granaio, Tosc is a nice stone building (70 sq m) with air conditioning and WiFi internet. The property can sleep up to four people comfortably in two bedrooms with one bathroom. Casa Anita - Castellina In Chianti - Granaio, Tosc is located 14 km (9 mi) from Castellina In Chianti, Italy and only 24 km (15 mi) from San Gimignano in the tourist area "San Gimignano And Surroundings".
Your Experience
Upon arrival you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. For your enjoyment you will find a 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 four people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: San Gimignano 24 km (15 mi), Greve In Chianti 27 km (17 mi), Siena 45 km (28 mi), Florence 52 km (32 mi) and Montalcino 81 km (50 mi).
Some other major tourist destinations you should consider visiting are: Florence 52 km (32 mi), Viareggio 143 km (89 mi), Forte Dei Marmi 153 km (95 mi), Rome 280 km (174 mi), Venice 299 km (186 mi) and Milan 346 km (215 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 18 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) 65 km (40 mi), Pisa (psa) 99 km (61 mi), Bologna (blq) 151 km (94 mi), Genova (goa) 284 km (176 mi) and Roma Ciampino (cia) 289 km (179 mi).
Additional Services
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Casa Anita - Castellina In Chianti - Granaio, Tosc
Villa Crispinino
Private Accommodation with WIFI, private pool, A/C, patio, pets allowed, panoramic view, near Arezzo
- 9
- 4
- 4
Description
This is an independent villa boasting beautiful views and its own swimming pool. Its dominating position, overlooking the Val di Chiana, is not far from the town of Civitella.
The villa itself has been recently refurbished however, it still holds its original character such as terracotta floors, wooden beams and stone arches.
Outside there is a large terrace and a large garden, both offering privacy and somewhere to relax in the open air. The property is surrounded by fencing.
Villa Crispinino is perfectly positioned for anyone hoping to visit Tuscany’s famous sites. About 20 km from the property, in the town of Arezzo, you can catch a train to destinations such as Rome, Florence, Orvieto and Siena.
Access to the property is via a dirt road (in great condition).
Distances: The nearby town of Civitella (4 km) can offer you food shops while Battifolle (10 km) can offer a large selection of shops. Arezzo lies 20 km away and slightly further afield are the cities of Siena (50 km), Florence (80 km), Assisi and Perugia (90 km).
Available to guests: Large, well-kept and furnished garden, swimming pool reserved exclusively for guests (10 x 5 m - depth 1.4 m) and barbecue.
The rental has free WI-FI and a Play Station.
Parking available on the grounds of the property.
Extra Services: Upon request, two children’s cots are available at no extra charge.
Please carefully check if there are any extra costs to be paid on site! Villa Crispinino
Book your vacation for the period from 04 April 2026 to 30 May 2026 and save 10% (minimum 7 nights).
Book 15 days or less before the arrival date and receive a 15 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Podere Sangiovese, Pool and View in Chianti
Unique independent house with private pool, WIFI, pets allowed and panoramic view
- 9
- 5
- 3
Description
Conveniently located 6 km (4 mi) from Castellina In Chianti, Italy in the tourist area "Siena And Surroundings" and only 27 km (17 mi) from Greve In Chianti. Podere Sangiovese, Pool and View in Chianti is a nice vacation rental (200 sq m) with private pool and WiFi internet. The property can sleep up to nine people comfortably in five bedrooms with three bathrooms.
The Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. 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, stove and refrigerator, as well as, plenty of tableware and cutlery for up to nine people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the nice Tuscan weather.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 27 km (17 mi), Siena 28 km (17 mi), San Gimignano 30 km (18 mi), Florence 61 km (38 mi) and Montalcino 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 61 km (38 mi), Viareggio 154 km (96 mi), Forte Dei Marmi 161 km (100 mi), Rome 263 km (163 mi), Venice 307 km (191 mi) and Milan 357 km (222 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Podere Sangiovese, Pool and View in Chianti. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 15:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 13 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) 73 km (45 mi), Pisa (psa) 108 km (67 mi), Bologna (blq) 160 km (99 mi), Roma Ciampino (cia) 272 km (169 mi) and Roma Fiumicino (fco) 284 km (177 mi).
Podere Sangiovese, Pool and View in Chianti
Civitella
Unique independent house with hot tub, WIFI, private pool, TV, panoramic view, close to Arezzo
- 8
- 4
- 2
Description
Independent house with private swimming pool located in a very scenic area in Valdichiana and surrounded by the countryside of Arezzo. Hectares of woodlands that circle the property ensure maximum privacy and a closeness with nature. The interior is in a rustic style. Outside, the guests can enjoy a private garden and a beautiful swimming pool with a great view and wooden solarium furnished with tables and chairs. Beside the swimming pool there is also a hot tub to enjoy.
This is an ideal set-up for those looking to spend a holiday in absolute tranquility.
The house is accessed via a stretch of roughly 4km of dirt road which is not adapted to low-lying/sports cars.
Distances: Civitella della Chiana with food stores and restaurants - 6 km, Battifolle with a wide variety of shops - roughly 15 km, Arezzo (train station) - 25 km, Monte San Savino - 25 km, Siena – roughly 75 km, Florence (airport) - 80 km, Perugia - 100 km.
Available: outdoor private and furnished area with tables, chairs and sun umbrellas, swimming pool reserved for the exclusive use of guests (9 x 3 m - depth 1,1 m – open from 01/04 to 15/10), outdoor shower with hot water (solar heated), barbecue, wood-burning pizza oven.
Onsite parking.
Please carefully check if there are any extra costs to be paid on site! Civitella
Medieval Castle Living: Vineyards, Swimming Pool &
Fantastic holiday home with private pool, WIFI, A/C, balcony and panoramic view, close to Siena
- 12
- 6
- 6
Description
Vacation rental Medieval Castle Living: Vineyards, Swimming Pool & is a beautiful stone building (800 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to 12 guests comfortably in six bedrooms with six bathrooms. Conveniently located 4 km (2 mi) from Sovicille, Italy in the tourist area "Siena And Surroundings" and only 14 km (8 mi) from Siena.
Nestled in the lush greenery of the Montagnola Senese, this magnificent property is a masterfully preserved 13th-century castle located just a 15-minute drive from the historic heart of Siena. The estate has been meticulously restored by its owners, who reside in the main tower in a secluded area that remains entirely private and separate from guest accommodations.
The estate is thoughtfully designed to offer both community and privacy. The first floor of the main castle features two charming apartments. Adjacent to the castle is a separate cottage housing two additional apartments, providing an ideal retreat for couples or guests seeking extra seclusion. With fully equipped kitchens in every unit and expansive common areas, the property perfectly balances independent living with shared moments.
Surrounded by rolling vineyards producing a refined selection of "Super Tuscan" wines, the estate invites you to embrace the slow pace of Italy. The grounds are a masterpiece of landscape design, featuring manicured lawns, traditional terracotta planters, and vibrant blooms. At the heart of the garden lies a generous swimming pool, fully outfitted with elegant sun loungers and umbrellas.
This elegant and spacious holiday home is perfectly suited for a luxurious escape with family or friends. The property comfortably accommodates up to twelve guests (with capacity for an additional two guests upon request).
The Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and playground. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished balcony is the perfect setting to enjoy food, family and the lovely Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 14 km (8 mi), San Gimignano 46 km (28 mi), Montalcino 49 km (31 mi), Greve In Chianti 53 km (33 mi) and Montepulciano 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 170 km (105 mi), Forte Dei Marmi 177 km (110 mi), Rome 248 km (154 mi), Venice 322 km (200 mi) and Milan 372 km (231 mi).
Additional Information
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 88 km (55 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 257 km (160 mi) and Roma Fiumicino (fco) 270 km (168 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a pleasant way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will organize the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the additional costs.
Meals - If you'd like to have meals provided during your visit, either half-board or full-board is available. If you prefer only breakfast be provided, that can be scheduled as well. Inquire about the additional costs.
Tours - The owner can arrange 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.
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.
Exclusive Estate Inclusions : elevate your stay, we offer these bespoke services upon reservation:
When you choose the Castle Experience, your stay includes a curated selection of authentic local luxuries:
- Gourmet Farm-to-Table Breakfast: Start your morning in the castle’s elegant common wing with a signature breakfast prepared by the Castellana (the Lady of the Castle). Every ingredient is organic and locally sourced ("Km 0"), with each dish prepared à la minute to your preference upon your arrival at the table.
- Estate Wine Tasting: Enjoy an exclusive guided tour of the castle with a private tasting in the castle’s historic cellar. This experience can be scheduled at your convenience with a simple advance reservation.
Bespoke Guest Experiences (Optional)
To further enhance your Tuscan retreat, we are pleased to arrange the following premium services:
- Dining with the Castellana: Enjoy an elegant, candlelit dinner hosted in the castle's private courtyard—an intimate glimpse into authentic noble life.
- Culinary Arts: Participate in private cooking classes or enjoy professionally catered buffet dinners.
- Outdoor Adventures: Explore the region with curated wine tours, guided bike excursions, or scenic hiking trips through the Montagnola Senese.
- Tuscan Traditions: Experience the thrill of a professional truffle hunting.
Medieval Castle Living: Vineyards, Swimming Pool &
Book now and save 10%. Offer valid until 10 May 2026 and for a minimum stay of 2 nights.
Villa le Caggia
Independent Villa with private pool, WIFI, hot tub, A/C, TV, patio, panoramic view, near Siena
- 16
- 7
- 7
Description
Property Villa Le Caggia is a nice stone building (500 sq m) that includes WiFi internet, hot tub and private pool. The property can sleep up to 16 people comfortably in seven bedrooms with seven bathrooms. Villa Le Caggia is located 6 km (4 mi) from Arnano, Italy and only 19 km (12 mi) from Siena in the tourist area "Siena And Surroundings".
What to Expect
When you arrive you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid vacation in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a patio, hot tub, playground and barbecue grill. There is a kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 16 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 19 km (12 mi), San Gimignano 33 km (20 mi), Greve In Chianti 53 km (33 mi), Montalcino 55 km (34 mi) and Florence 68 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (43 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 170 km (106 mi), Rome 254 km (158 mi), Venice 319 km (198 mi) and Milan 362 km (225 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Le Caggia. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 15:00 - 22:00
Check-Out Time: 00:00 - 10:00
Pool Open: 15 March - 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) 83 km (52 mi), Pisa (psa) 116 km (72 mi), Bologna (blq) 168 km (104 mi), Roma Fiumicino (fco) 250 km (155 mi) and Roma Ciampino (cia) 264 km (164 mi).
More 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 discovering the secrets required to prepare mouth-watering 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 delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the 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.
Maid Service - Upgrade your vacation with maid service. This service can be arranged by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Villa Le Caggia. Inquire for more details, including the supplemental cost and how to arrange this service.
The villa is equipped with an electric fence that is activated at night to protect the outdoor areas from wild animals.
Pets are welcome (even more than one), but we cannot guarantee that dogs will not wander off. Villa Le Caggia
Villa Aiale
Independent Accommodation with private pool, WIFI, A/C, TV, patio, panoramic view, near Montalcino
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- 7
- 8
Description
Villa Aiale is located 2 km (1 mi) from Bibbiano, Italy and only 21 km (13 mi) from Montalcino in the tourist area "Orcia Valley". Holiday rental Villa Aiale is a nice property (500 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to 14 people comfortably in seven bedrooms with eight bathrooms.
What to Expect
When you arrive at Villa Aiale you’ll find a lovely clean well-maintained property with views of the hills perfect for a relaxing holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. Outdoors 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 and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people.
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: Montalcino 21 km (13 mi), Siena 38 km (24 mi), Montepulciano 53 km (33 mi), Arezzo 77 km (48 mi) and Cortona 78 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 106 km (66 mi), Viareggio 200 km (124 mi), Forte Dei Marmi 207 km (129 mi), Rome 229 km (142 mi), Milan 400 km (249 mi) and Naples 420 km (261 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
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) 119 km (74 mi), Pisa (psa) 154 km (96 mi), Bologna (blq) 205 km (128 mi), Roma Fiumicino (fco) 232 km (144 mi) and Roma Ciampino (cia) 238 km (148 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 discovering the techniques needed to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your 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 - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Maid Service - If you'd like maid service during your visit that can be arranged by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Ask for more details, including the supplemental cost and how to organize this service.
Villa Aiale
Casale Il Giglio
Unique private villa rental with WIFI, private pool, TV, pets allowed and panoramic view
- 10
- 5
- 5
Description
Property Summary
Civitella In Val Di Chiana, Italy is home to a charming cottage that has recently undergone renovations. Divided into two spacious parts, each with its own private garden spanning 400 square meters, this property offers a peaceful retreat surrounded by a large fenced garden shared with the owner's nearby residence. The cottage boasts well-maintained interiors, featuring terracotta and parquet flooring, beamed ceilings, stone archways, and bedrooms equipped with ceiling fans and wrought iron beds. A highlight is the refreshing swimming pool, complemented by an outdoor hot water shower, offering stunning views of the sunflower fields that characterize the Tuscan landscape. Additionally, guests can enjoy private gated access and a video entry phone for added security and convenience during their vacation rental stay.
Outdoors
The outdoor spaces of this property are truly remarkable. Guests can indulge in a refreshing swim in the stunning swimming pool, complete with an outdoor hot water shower while taking in the breathtaking views of the sunflower fields, a quintessential part of the Tuscan landscape. As the sun sets, the famous Gargonza castle provides a picturesque backdrop. The property also features a spacious, fenced garden of 800 square meters, providing ample space for outdoor activities and relaxation. The uniquely shaped pool is surrounded by various amenities, including an outdoor shower, table tennis, boules, and comfortable garden furniture, ensuring a delightful holiday rental experience.
Other Information
The charming working farm "Casale il Giglio" offers a cozy and authentic experience for guests. Renovated in 2004, this property is conveniently located just 5 kilometers from the center of Monte San Savino. Guests can enjoy a range of amenities during their stay, including WiFi, table football, and bicycles (4). Heating is available for an additional fee from November 1st to April 15th. The property is well-suited for families and seniors, and the owner resides on the same premises.
Distances and Attractions
The property's prime location offers easy access to numerous attractions in the surrounding areas. Lucignano is just 12 kilometers away, while Rapolano Terme is 28 kilometers from the property. Cortona (32 km), Montepulciano (37 km), and Gaiole in Chianti (45 km) are also within convenient driving distances. Guests should note that having a car is recommended to fully explore the region's charms during their vacation rental stay. With its proximity to renowned destinations, this property provides an ideal base for discovering the rich cultural heritage and natural beauty of Tuscany. Casale Il Giglio
Le Terrazze
Amazing private holiday rental with A/C, private pool, hot tub, WIFI, TV, patio and pets allowed
- 6
- 3
- 3
Description
Property Summary
Le Terrazze is a charming rustic house with two storeys, terraced and located just 4 kilometers away from the center of Monte San Savino and 5 kilometers away from the center of Civitella Val di Chiana in Italy. It boasts a beautiful garden with a lawn and trees, as well as a large seasonal swimming pool measuring 12 x 5 meters. Guests can enjoy internet access, parking on the premises, and the option for breakfast and half board meals for an additional fee. The vacation rental also offers a pre-arrival grocery service for added convenience.
Outdoors
The property is situated on a massive 2-hectare lot that features a natural pond for shared use. The private property is fenced and covers an area of 600 square meters. Guests can enjoy the outdoor shower, table tennis, arbour, and garden furniture in the spacious outdoor area.
Other Information
The nearest shop, restaurant, and bar are all just 600 meters away, while the railway station "Albergo" is only 1 kilometer away. For those interested in horseback riding, a riding stable is located just 700 meters from the property. Farm products are available for local sale, and a permit is required for fishing, with an additional fee. The owner of the property lives on the same lot, and there are animals in the neighborhood.
Distances and Attractions
Nearby attractions include Arezzo, which is just 15 kilometers away, Montepulciano, located 40 kilometers away, and well-known lakes such as Trasimeno, easily accessible at just 50 kilometers away. Additionally, a lovely lake is situated just 500 meters away from the property. Le Terrazze
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- 4
- 3
Description
Property Summary
Casa Clotilde is a charming, renovated country house located in the tranquil countryside just 4 km from the center of Monte San Savino and 5 km from the center of Civitella In Val Di Chiana, Italy. This vacation rental features a private, fenced garden of 350 m2 with a lawn and trees, as well as a large swimming pool (13 x 7 m) available from 09.Apr. to 30.Sep. with a depth of 120 - 180 cm, ideal for both adults and children. Guests can enjoy internet access and central heating system within the house.
Outdoors
The property boasts a private, fenced garden of 350 m2 with a lawn and trees, as well as a large swimming pool (13 x 7 m) that is available from 09.Apr. to 30.Sep. The pool has a depth of 120 - 180 cm, making it ideal for both adults and children. The garden also features an outdoor shower, volleyball court, arbour, garden furniture and a barbecue, providing plenty of opportunities for outdoor activities and relaxation.
Other Information
Breakfast and half board are available upon request at an extra cost, as well as a pre-arrival grocery service. The property also has a roofed parking area for two cars. For those who enjoy fishing, a permit is required and the property offers the option of purchasing local farm products.
Distances and Attractions
Nearby attractions include the beautiful city of Arezzo, situated only 15 km away, and the picturesque town of Montepulciano, which can be reached in 40 km. There is also an equestrian center in Arezzo, just 10 km away, making it a convenient location for those interested in horseback riding. Casa Clotilde
Il Borgo di Gebbia
Independent Holiday rental with private pool, WIFI, TV, terrace, panoramic view, near Arezzo
- 10
- 5
- 6
Description
Property Summary
Nestled within a picturesque Tuscan village and perched atop a hill overlooking the breathtaking landscapes of the Val Di Chiana countryside, Il Borgo di Gebbia is a charming country house that offers an exceptional vacation rental experience in Civitella In Val Di Chiana, Italy. Thoughtfully renovated in 2014, this elegant retreat sits 500 meters above sea level, providing a tranquil and private atmosphere that perfectly complements the natural beauty of its surroundings. The property extends across more than 2 hectares of land, ensuring ample space and a genuine sense of seclusion. Guests benefit from convenient on-site parking, allowing for effortless arrivals and easy exploration of the surrounding region. Reliable internet and WiFi connectivity are available throughout the property, keeping you connected whenever needed. The fenced above-ground swimming pool, measuring 7 x 4 meters with a depth of 120 cm, serves as a centerpiece of outdoor leisure and is open seasonally from May to September, offering a refreshing retreat during the warmer months.
Outdoors
The outdoor spaces at Il Borgo di Gebbia are a true reflection of the Tuscan countryside that surrounds them. The above-ground swimming pool, enclosed by a safety fence, provides a secure and inviting environment for relaxation and recreation throughout its seasonal availability from May to September. Set against the backdrop of rolling hills and open countryside, the expansive grounds spanning over 2 hectares invite you to explore, unwind, and fully immerse yourself in the serene natural environment. The elevated position of the property, at 500 meters above sea level, ensures that the outdoor areas are graced with sweeping panoramic views of the Val Di Chiana valley, making every moment spent outside a genuinely memorable experience.
Other Information
Il Borgo di Gebbia offers a selection of thoughtful services designed to enhance your stay. Weekly room cleaning is included, ensuring that the property remains comfortable and well-maintained throughout your visit. For those who wish to enjoy home-cooked meals without the effort, a cook can be arranged upon request for an additional fee. Breakfast service is also available at an extra charge, providing a convenient and pleasant way to start each morning.
Distances and Attractions
Il Borgo di Gebbia enjoys an enviable location that places a wealth of Tuscan destinations and local amenities within easy reach. The center of Civitella in Val di Chiana, a quaint village offering a genuine glimpse into traditional Tuscan life, is just 3.5 km from the property. Everyday conveniences are close at hand, with the nearest shop located 3.5 km away and a supermarket reachable within 8 km. A restaurant can be found within just 2 km of the property, making dining out a simple and enjoyable option. For those who enjoy an active lifestyle, tennis courts are situated 14 km away, horseback riding opportunities are available 6 km from the property, and an 18-hole golf course can be found 23 km away. The renowned thermal baths of Rapolano Terme are located 44 km from Il Borgo di Gebbia, while the Castiglion del Lago bathing lake is 69 km away. The historic city of Arezzo lies 23 km from the property, and the celebrated city of Siena is 52 km away. Art and history enthusiasts will appreciate the proximity of Cortona at 42 km, Castelnuovo Berardenga at 36 km, and the charming towns of Gaiole in Chianti, Montepulciano, and Pienza, all within 63 km. Florence, the magnificent capital of Tuscany, is located 84 km away and is easily accessible by car, making it an ideal destination for a day trip. Il Borgo di Gebbia
- 4
- 2
- 2
Description
Property Summary
Nestled in the picturesque rolling landscape of Castellina in Chianti, Italy, Villa Elisa is a beautiful and comfortable holiday rental set in a sunny, elevated residential area surrounded by other villas and the serene Tuscan countryside. Located approximately 2 kilometres from the centre of Castellina in Chianti, this charming property offers a peaceful retreat with easy access to the region's most celebrated destinations. The villa benefits from reliable WiFi connectivity, keeping you effortlessly connected throughout your stay. Parking is conveniently available directly at the property, accommodating up to 2 cars, making it ideal for guests arriving by road. The shared fenced garden, adorned with flowers and mature trees, provides a welcoming outdoor setting where you can fully appreciate the tranquillity of the Chianti countryside.
Outdoors
The outdoor spaces at Villa Elisa are designed to complement the natural beauty of the surrounding Tuscan landscape. The shared garden, enclosed by a fence for added privacy and security, is thoughtfully landscaped with a variety of flowers and trees that create a colourful and relaxing atmosphere throughout the seasons. For a more indulgent outdoor experience, the property features a private hot tub, offering you the perfect opportunity to unwind and enjoy the warmth of the Italian sun or the stillness of a quiet evening under the Chianti sky. The elevated position of the property ensures exceptional light and pleasant breezes, enhancing every moment spent outdoors.
Other Information
Villa Elisa is equipped with air conditioning, ensuring your comfort during the warmer months of the Tuscan summer. Baby equipment is included as part of your stay, making the property a convenient and welcoming choice for families travelling with young children. Please be aware that groups of teenagers are accommodated on request only. It is also worth noting that part of the house remains closed and unoccupied during your stay, and the owner resides in a separate semi-detached house on the property.
Distances and Attractions
Villa Elisa enjoys a privileged location that places you within easy reach of some of Tuscany's most iconic towns and attractions. A bus stop named "Chiantigiana" is situated just 100 metres from the property, offering a convenient public transport option for those wishing to explore the region without a car. Everyday essentials are readily accessible, with a shop, grocery store, and supermarket all located 2 kilometres away. The charming hilltop town of Radda in Chianti is just 10 kilometres from the villa, while the medieval village of Greve in Chianti and the lively town of Gaiole in Chianti are both approximately 15 kilometres away. The magnificent city of Siena, with its world-renowned Piazza del Campo and Gothic cathedral, lies 20 kilometres from the property, and the extraordinary art city of Florence can be reached in approximately 65 kilometres, making Villa Elisa an ideal base for discovering the very best of Tuscany. Villa Elisa
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- 2
- 1
Description
Property Summary
Nestled in a secluded and quiet area, the newly renovated Country house "Olivo" is a charming and detached vacation rental located just 500m from the center of Castellina In Chianti, Italy. The property boasts a beautifully maintained 500m2 garden that is fully fenced, providing a safe and secure place for guests to relax and unwind. It offers amenities such as a Swimming Pool, Yard, Internet Wifi, and Parking, making it an ideal holiday rental for those seeking a comfortable and convenient stay in the stunning Tuscan countryside.
Outdoors
The property's outdoor area is a true highlight, featuring a refreshing swimming pool (8 x 3 m, depth 130cm) available for use during the seasonal months from 01.Apr. to 31.Oct. Guests can enjoy an outdoor shower, pergola, garden furniture, and barbecue, creating the perfect setting for alfresco dining and socializing in the beautifully maintained 500m2 fully fenced garden.
Other Information
Heating is available from 01.11. to 07.04. and must be paid for on-site. The property is conveniently located within walking distance of grocery stores and supermarkets, allowing guests to easily stock up on essentials. For those seeking relaxation and rejuvenation, the thermal baths "Rapolano Terme" are just 52km away.
Distances and Attractions
Strategically positioned just 26km from the center of Siena and 48km from the center of Florence, Country house "Olivo" serves as an excellent base for exploring the breathtaking Tuscan countryside. Nearby attractions within a short driving distance include San Donato in Poggio, Radda in Chianti, Panzano in Chianti, Greve in Chianti, Monteriggioni, San Gimignano, Siena, and Volterra, offering a range of activities such as hiking, cycling, and exploring the picturesque towns and villages. Olivo
