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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 1327 Villas in Castel San Gimignano with updated reviews, rates, and availability.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (47)
"Nice house with a beautiful pool , well located to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (34)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Outdoor pool, a heated pool

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (87)
"Fantastic location, stunning views, and amazing pool"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Outdoor pool

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (39)
"The villa is quiet and so picturesque. The views are incredible. The accommodations comfortable and the outdoor space absolutely amazing!"
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Authentic Tuscan country house, dating back to around the year 1000
Outdoor pool

Authentic Tuscan country house, dating back to around the year 1000

9.6 out of 10, Exceptional, (50)
"We spent our last week of our 3 weeks in Italy in Marila’s home and are so happy we did! The location was fantastic, the home was perfect for us and Marilia was a warm and gracious host. We asked her to help with booking a chef to come in to teach a class, a wine tour and restaurant suggestions and all were fantastic. We would love to go back again!!"
Authentic Tuscan country house, dating back to around the year 1000
Villa with view and private pool
Outdoor pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"The villa is perfect & very comfortable. The location is awesome being a short drive from Volterra and also very central to all of the Tuscan towns. We would definitely stay again!"
Villa with view and private pool
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor 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
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (84)
"This house is beautiful, perfectly situated, and well maintained! Alessandro was so kind and we enjoyed every moment of our stay! "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (96)
"Clean, very convenient, friendly.... Everything was super!"
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Exterior

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

9.8 out of 10, Exceptional, (67)
"We loved our stay here. It was a little challenging to find the first time but so nice and quiet. Everything was as just as described. It was a wonderful experience."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Terrace/patio

Casa Farsetti - Exclusive villa with private pool between Siena and Florence

9.4 out of 10, Exceptional, (20)
"A true hidden gem outside of Firenze. Old but very charming building in a beautiful scenery!"
Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Beautiful Villa With Panoramic Views near San Gimignano
Outdoor pool

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"Nice area! We enjoyed the terasse and the pool a lot "
Beautiful Villa With Panoramic Views near San Gimignano
Exclusive Farmhouse Pool & View of San Gimignano
Outdoor pool

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Fridge, microwave, oven, stovetop

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
Outdoor pool

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

Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena
Villa Casa al Sole Large Private Pool, WiFi
Pool

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"Outstanding Villa. Vert comfortable and great location. Loved this place."
Villa Casa al Sole Large Private Pool, WiFi
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
Property grounds

Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay at Le Vecchie Villa near Radda Italy. The views from our villa were magnificent, olive trees and vineyards surrounding the property. It's a bit of a steep climb on the unpaved road to the property so drive slow and steady. I'd recommend guests get a vehicle with a sufficient ground clearance to avoid the ruts on the road. We experienced some rain, so it was nice to stay in for the day and play games and sample our many Italian food delights purchased at the local Coop grocery...
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
Villa San Miniato Corniano: Iconic 5 Bedrooms Farmhouse with Pool
Pool

Villa San Miniato Corniano: Iconic 5 Bedrooms Farmhouse with Pool

10.0 out of 10, Exceptional, (6)
"We had a very warm welcome by Manuel who could not of been more helpful. The property is full of character and as with the beautiful grounds you can spend quality time with family and friendsjust have time with yourself enjoying the scenery. I would just like to say (on behalf of our party) a big thank you to all concerned for making our stay so memorable and would recommend the Villa."
Villa San Miniato Corniano: Iconic 5 Bedrooms Farmhouse with Pool
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
Suite | Minibar, soundproofing, iron/ironing board, free WiFi

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (154)
"Fabulous property and staff. Rita was so helpful when our car had to be towed, we wouldn't have been able to continue our trip with out her and the other team members help. The people here are amazing."
The price is AED 746
AED 837 total
includes taxes & fees
28 Apr - 29 Apr
Il Battistero Siena - Residenza d'Epoca
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Camping Boschetto Di Piemma
Outdoor pool

Camping Boschetto Di Piemma

3.0 star property
8.8 out of 10, Excellent, (74)
"Great experience, close to a beautiful city and castle on a hill. "
The price is AED 169
AED 198 total
includes taxes & fees
6 May - 7 May
Camping Boschetto Di Piemma
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.