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Compare 608 Villas in Montecastelli with updated reviews, rates, and availability.

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
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
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 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
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
9.8 out of 10, Exceptional, (16)
"It was a perfect stay! Very helpful hosts with great local suggestions."
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
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
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
10.0 out of 10, Exceptional, (96)
"The spacious accommodation on the first floor offered captivating views over the Tuscan countryside to San Gimignano on the horizon.The garden with its spacious swimming pool and outdoor eating area was greatly enjoyed by everyone. San Gimignano itself was a lovely town to explore with great restaurants and cafes. And the meal prepared for us by Barbara was very special."
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
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 Osservatorio for up to 11 with private pool, 15mins to San Gimignano
10.0 out of 10, Exceptional, (41)
"Fantastic Villa, suitable for all ages ( our guest ranged from 12 to 80 years). Great location, near to all local attractions. Would recommend to family and friends."
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
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
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)
"We had an incredible time at Villa Sarah. As amazing as the photos are, they do not do justice to the beauty of the villa and the surrounding countryside. The view from the pool is unlike anything else you will experience and is alone worth the price of the villa. We rented the villa for 7 nights with 10 adults and 2 children, which were easily accommodated. Gabriel, Caterina, and team were incredibly responsive and easy to work with and they were able to recommend a number of activities...
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
Villa Costa, Stunning Villa in the heart of Tuscany.
10.0 out of 10, Exceptional, (31)
"I stayed at this property for 1 week with my parents, my sisters and their husbands and 3 children (aged 1-6) and all I can say is what a wonderful villa. The layout was ideal for us. 3 bedrooms were located upstairs accessed by the external stairs, 2 had en-suites and the other had a bathroom next door) and there was also a seating area up there. One bedroom was based downstairs off the main living area with a bathroom next door. And the other bedroom was in the annexe which was accessed...
The price is AED 1,558
AED 1,775 total
includes taxes & fees
23 Oct - 24 Oct
Villa Costa, Stunning Villa in the heart of Tuscany.
San Gimignano - Panoramic garden and beautiful pool!
9.8 out of 10, Exceptional, (36)
"This magnificent villa and the hosts, Cristina and Simone, surpassed our expectations and made a blissful stay in beautiful San Gimignano. The 300+ year old home was clean, charming and authentic and the grounds were well maintained and serene. The views of the countryside were breathtaking! At our request, the hosts arranged for a chef, Patrizia, to come to prepare dinner on 3 evenings. She was delightful and used fresh produce and ingredients from her own farm in the multi-course meals she...
San Gimignano - Panoramic garden and beautiful pool!
Delightful villa in the heart of Tuscany
10.0 out of 10, Exceptional, (53)
"We LOVED staying at villa le Bolli. We had an intimate wedding here and it was absolutely beautiful. The property is clean with great upkeep and amazing views. Pierre went above and beyond to meet our needs. Would love to return for an anniversary."
Delightful villa in the heart of Tuscany
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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 AED 201
AED 222 total
includes taxes & fees
24 Sep - 25 Sep
Camping Boschetto Di Piemma
ApartHotel Anghel
8.2 out of 10, Very Good, (303)
"Nice place, quiet and clean!"
The price is AED 329
AED 372 total
includes taxes & fees
21 Oct - 22 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.