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Compare 647 Villas in Montecastelli with updated reviews, rates, and availability.

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (92)
"Lovely large 4 bedroom house with spectacular views of San Gimignano. Really enjoyed our stay and highly recommend this rental. Everything was perfect including the pool. Alessandro "
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (79)
"This was our second villa rental in the San Gimignano area, our first at Alessandro's villa and it was amazing! Alessandro was very responsive and helpful from the moment we booked the year prior, until the day we checked out. We were a group of 6 adults and had plenty of room. The villa has every amenity you might need during your stay. At check in Alessandro provided us with helpful information about the surrounding area. The villa is in a beautiful setting surrounded by vineyards and olive...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
15th century barn fully renovated in a stylish style with gorgeous swimming pool
10.0 out of 10, Exceptional, (4)
"The renovated barn has been lovingly and tastefully transformed into a beautiful Tuscan villa—the perfect base for our family’s first visit to the area. The space is truly unique in all the ways it has incorporated modern design and amenities while preserving the rustic charm of the structure. The rooms and furnishings are comfortable, and the kitchen is a great place to prepare a meal with fresh local ingredients. The location was ideal for our itinerary, as we could easily visit Siena and San...
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Villa luna with pool and garden near the center of Siena
8.8 out of 10, Excellent, (25)
"Wonderful location. Loved the view, the pool, the outdoor bbq area"
Villa luna with pool and garden near the center of Siena
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Casa Martina-Detached house, fenced garden and swimming pool for exclusive use!
9.4 out of 10, Exceptional, (8)
"The house is superb. The patio is covered and lit romantically. It offers insect repellent light. The pool is clean and shady during the day (chairs, not the pool itself). It is also fenced, as is the whole property, which helps if you travel with children or pets (dogs have their own outside bar installed). Rooms are spacious and have misquote nets which is extremely rare. They are also air conditioned. Kitchen is well equipped. The owners are extremely nice and welcoming. They will take care...
Casa Martina-Detached house, fenced garden and swimming pool for exclusive use!
Villa with private swimming pool in quiet area, private garden, panoramic views
10.0 out of 10, Exceptional, (7)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
Villa with view and private pool
10.0 out of 10, Exceptional, (19)
"We thoroughly enjoyed our stay at the villa. It was relaxing and comfortable and well stocked. Gullia did an amazing job giving suggestions of places to go and things to do. We wish the pool would have been heated bc the weather was chilly during our stay but everything else was perfect."
Villa with view and private pool
Historic villa in the heart of Tuscany. Surrounded by nature.
9.8 out of 10, Exceptional, (37)
"We had such a lovely week. The house was amazing and the host was so helpful. We had two local ladies come and make a feast - definitely have them bring the local wine and dessert. Watching the sunset above the pool was wonderful and the ping pong table was a big hit with our teens. Getting there was a little tough and it was a little far away from some of the places we wanted to visit- not because they were far, but due to the winding roads that slow travel. To get there we mapped to the...
Historic villa in the heart of Tuscany. Surrounded by nature.
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
9.0 out of 10, Wonderful, (2)
"Très belle maison et cadre agréable "
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
10.0 out of 10, Exceptional, (42)
"Great villa"
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
8.8 out of 10, Excellent, (13)
"Schöne super große Unterkunft auf einem umzäunten Gelände. Pool ist super und ebenfalls umzäunt. Kleine Grillstelle und Outfoorküche die wir immer genutzt haben"
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
3-person apartment in Tuscan farmhouse
10.0 out of 10, Exceptional, (3)
"Nice appartment. Great views of Tuscan countryside. Close to Riparbella which has restaurants and shops and about 10km to the coast."
3-person apartment in Tuscan farmhouse
panoramica casa con piscina privata
7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
panoramica casa con piscina privata
Beautiful Villa With Panoramic Views near San Gimignano
9.6 out of 10, Exceptional, (69)
"The villa is in a lovely location with stunning views across Tuscan countryside and mountains. Some great sunsets while barbecuing in the evening. It was very comfortable and the air conditioning in the bedrooms was great and essential during a very hot August. It was smaller than we expected, fine for the two of us but would have been quite crowded with 4 or 6. The swimming pool was lovely but was shared with more villas than we had expected, not a problem in the morning or late evening but...
Beautiful Villa With Panoramic Views near San Gimignano
villa con vista panoramica
9.0 out of 10, Wonderful, (2)
"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"
villa con vista panoramica
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
10.0 out of 10, Exceptional, (111)
"Owners arranged chef prepared dinner one night. They also did a cooking class/dinner another night. Both were amazing. Property is as spectacular as you can imagine and centrally located. Rent a car to get around. Owners helped make other arrangements for our daily excusions."
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
10.0 out of 10, Exceptional, (38)
"Villa Sarah was lovely and the setting was spectacular. The outdoor spaces and pool were great for cooking and relaxing. The view was postcard perfection! The staff gave us great recommendations and helped to organize transportation. We had a welcome dinner at the Villa which was a highlight."
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
VILLA ELEONORA Indipendent villa with private garden and private outdoor pool
9.2 out of 10, Wonderful, (15)
"We had a memorable vacation at this villa. It was everything that we expected and more. The villa is very well situated within Tuscany. Sienna, Florence, San Gimignano, Colle Di Val D'Elsa and Volterra are all within easy reach by car or by train. The villa is huge and the views to the rear are breath-taking. The villa was clean and tidy with everything that we needed close at hand. Luca was extremely welcoming and was always on hand if we needed him. Thank you for your hospitality. This is a...
VILLA ELEONORA Indipendent villa with private garden and private outdoor pool
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Montecastelli

Camping Boschetto Di Piemma
3.0 star property
9.0 out of 10, Wonderful, (68)
"Nice quiet spot in the woods but very close to San Gimignano. Very clean. Comfortable beds. They don’t provide towels or soaps, but that is clear up front. You can rent towels if you want and they sell soap/ shampoo in the office. "
The price is SAR 210
SAR 231 total
includes taxes & fees
1 Oct - 2 Oct
Camping Boschetto Di Piemma
ApartHotel Anghel
8.2 out of 10, Very Good, (303)
"Nice place, quiet and clean!"
The price is SAR 401
SAR 451 total
includes taxes & fees
14 Oct - 15 Oct
ApartHotel Anghel
panoramica casa con piscina privata
7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
panoramica casa con piscina privata
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.