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Compare 1085 Villas in Castel San Gimignano with updated reviews, rates, and availability.

Villa Casa al Sole Large Private Pool, WiFi
Beautiful villa with private pool, terrace, and garden

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (19)
"This is a beautiful villa with plenty of space for our large group. It is in a remote location and very quiet. It was perfect for short trips to local towns and then a swim in the afternoon. We spent most evenings on the patio enjoying the Tuscan sunsets. We would definitely stay again! "
Villa Casa al Sole Large Private Pool, WiFi
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Private pool

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Archipettoli - a historical manor house with stunning panoramic views
Pool

Archipettoli - a historical manor house with stunning panoramic views

10.0 out of 10, Exceptional, (34)
"What a wonderful privilege to stay in a house with such history and beauty inside and out! Beautifully restored, comfortable and charming. We were very happy to spend several evenings there, including one where our hosts arranged for a cook to come in, at our request (wonderful food!). The sunsets were stunning, and we got a beautiful vista and breezes. We did take advantage of the great location though, with day trips to Florence, Siena, Volterra and Panzano.Giampaulo and his wife were easy to...
Archipettoli - a historical manor house with stunning panoramic views
Beautiful Villa With Panoramic Views near San Gimignano
Collinella 14. A fully restored 3 bedroom, 2 bathroom semi detached house.

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"We had a wonderful stay and this property provided a nice central location from which to explore the region. Information from Steve was timely and extremely helpful. "
Beautiful Villa With Panoramic Views near San Gimignano
Villa luna with pool and garden near the center of Siena
Outdoor dining

Villa luna with pool and garden near the center of Siena

9.0 out of 10, Wonderful, (27)
"The home had everything we needed. The view from the villa was truly picturesque. A+++++!"
Villa luna with pool and garden near the center of Siena
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Exterior

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Pool

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

10.0 out of 10, Exceptional, (113)
"From the first contact until our checkout, the communication was excellent. The Villa was very well decorated and provided an excellent venue for our 12 person group. The chef and hostess prepared a delicious meal and extraordinary service. The Villa provided an excellent place to rest for our group. Everyone had their own bedroom and bathroom. Caterina, Gabriel and Carolina were EXCELLENT to work with! I would definitely recommend this Villa to anyone looking for a central location in...
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Villa Simo, absolute tranquility

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (67)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
View of the Villa from garden-pool

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
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa seen from the pool

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

10.0 out of 10, Exceptional, (56)
"Stay was excellent, a great house. Owners were super helpful. A property with over 100 olive trees. If I return this is where I will be 😎"
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa with private swimming pool in quiet area, private garden, panoramic views
Pool

Villa with private swimming pool in quiet area, private garden, panoramic views

10.0 out of 10, Exceptional, (8)
"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
Pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
The property has a private road and gate

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
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Our Anglican Church friends (three couples) from Texas began our Italy tour in Rome and then continued to Florence for a few days. We spent our final four days at the beautiful Villa Santa Chiara, a short walk from the gates of downtown Siena, Italy. This wonderful villa could accommodate more people than our group of six, but it was an excellent choice for our three couples. Each couple had their own private apartment with a bathroom, kitchen, and spacious living area. The villa was...
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Pool

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (29)
"Lovely rustic property in scenic location, large garden grounds and decent swimming pool. Property worked well for our family of 7 adults ranging three generations."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Il Boschetto an oasis of peace and nature in Siena
Exterior

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (31)
"The location was excellent, 30 minute walk (2.1 km) to the main gate of Siena or 15 minute bus ride (bus stop 25 meters from the house). The home is beautiful, lots of amenities, it was very rustic. The pool area could use a good trimming, the online photos showed the property better than it actually was but not too far off."
Il Boschetto an oasis of peace and nature in Siena
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Pool

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.6 out of 10, Exceptional, (17)
"Our 2-wk. reservation (Oct. 5-19) was actually increased by a week Sept. 28-Oct. 5, making it a 3-wk reservation, however, due to a medical issue, we had to return to the USA 10 days early. Gabriella was a wonderful property manager assisting us with seeking medical and hospital care. Lovely property and location."
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax
Pool

Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax

9.8 out of 10, Exceptional, (63)
"Stay was wonderful. Host met us upon arrival and explained everything to us. The only small comment would be that a regular toaster would be nice. "
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax
Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
Pool with seating area Villa Casa Collina

Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service

Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
Macia Viva, Castellina in Chianti, Siena and Chianti
Pool

Macia Viva, Castellina in Chianti, Siena and Chianti

8.0 out of 10, Very Good, (2)
"The views were beyond compare! Proximity to Castellina in Chianti was wonderful and the management team were responsive to a few issues. My main comment would be, especially considering the rental cost, that the furniture and kitchen supplies (dishes etc) needs upgrading and the quality of the beds/linens should be improved. Overall however, it was a lovely stay! Grazie."
Macia Viva, Castellina in Chianti, Siena and Chianti
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 Castel San Gimignano

Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (146)
"Spectacular view from our balcony! Close to the Duomo and Piazza del Campo, great restaurants and shopping. Highly recommend!"
The price is SAR 512
SAR 579 total
includes taxes & fees
6 Jan - 7 Jan
Il Battistero Siena - Residenza d'Epoca
La Terrazza Sul Campo Rooming House
Exterior

La Terrazza Sul Campo Rooming House

9.6 out of 10, Exceptional, (221)
"Excellent location. Excellent service. Great view from the balcony. "
The price is SAR 393
SAR 448 total
includes taxes & fees
9 Jan - 10 Jan
La Terrazza Sul Campo Rooming House
ApartHotel Anghel
Room

ApartHotel Anghel

8.2 out of 10, Very Good, (307)
"Nice place, quiet and clean!"
The price is SAR 280
SAR 324 total
includes taxes & fees
16 Jan - 17 Jan
ApartHotel Anghel
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.