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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 1130 Vacation Homes in Castel San Gimignano with updated reviews, rates, and availability.

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Terrace/patio

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)

9.8 out of 10, Exceptional, (47)
"It was amazing. House is beautiful and very clean with a gorgeous view. Sara and family were very helpful to us. "
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Casa Vacanze Le Case
Outdoor pool

Casa Vacanze Le Case

9.0 out of 10, Wonderful, (7)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
The price is AED 343
AED 397 total
includes taxes & fees
16 Apr - 17 Apr
Casa Vacanze Le Case
Nobleman holiday house in Tuscany with private swimming pool, A/C and Wi-Fi
Outdoor dining

Nobleman holiday house in Tuscany with private swimming pool, A/C and Wi-Fi

9.2 out of 10, Wonderful, (31)
"We had a great time in Radicondoli. Really enjoyed the village and both restaurants were fantastic. People were very friendly and our host was great. Highly recommend the coffee shop for breakfast and took full advantage of the laundromat in town. Views from the patio were amazing. Look forward to returning and highly recommend. "
Nobleman holiday house in Tuscany with private swimming pool, A/C and Wi-Fi
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Outdoor pool

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (21)
"We have just returned from a wonderful 10 night stay at Porcilia. The property was exactly as advertised and Francesca was a very welcoming and helpful host. The property was clean and well equipped. The pool was excellent and loved by all our party! The pool and the grounds were all very well maintained! We would highly recommend a stay at Porcilia!!"
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
The Porchereccia delle Bartaline
Exterior

The Porchereccia delle Bartaline

9.4 out of 10, Exceptional, (14)
"Great place and being in person is better than the on-line pictures. Beautiful views over looking the valley and vineyards below. Centrally located for plenty of great roadtrips. Enjoy!"
The Porchereccia delle Bartaline
Farmhouse in the heart of the real chiantishire
Exterior

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (131)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Pool

Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.

9.8 out of 10, Exceptional, (59)
"My wife and I had a wonderful time. Our host Marilia is lovely and gave very helpful recommendations for vineyards, restaurants and cooking classes in the area. The view and surrounding area is breathtaking!"
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Outdoor pool

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

9.8 out of 10, Exceptional, (72)
"The house is picture perfect - and the views are absolutely stunning. As others have said, to get to it, you need to drive down a bit of bumpy dirt road (so having a SUV would be a wise choice), but once you get there l, the pure serenity and peacefulness of the Tuscan hills await you. It was so relaxing and quiet and really felt like you had it all to yourself. The house itself was great - 4 large bedrooms and 2 large bathrooms (especially for European standards) provided plenty of space to...
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Property grounds

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany

9.6 out of 10, Exceptional, (46)
"The villa was a fantastic opportunity to get away from the hustle of city life. The local town was old world and friendly. The restaurant, La Toppa, was amazing. The owner of the restaurant & villa ands his family was very friendly, responsive and helpful. Wonderful stay in Tuscany. "
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Chianti Craft House Badia a Passignano
Point of interest

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"The apartment is at the heart of the small village, central to several great restaurants and practically across the street from the incredible 11th century abbey. The place was very clean and has been recently renovated, but still had a very historic feel to it. Emanuel, our host, was very friendly and gracious. He offered several personal recommendations to restaurants and a wine tasting at a nearby castle, all of which were great! Would definitely stay here again!"
The price is AED 619
AED 869 total
includes taxes & fees
7 Apr - 8 Apr
Chianti Craft House Badia a Passignano
Charming apartment in the Historic Center of Siena
TV

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"This is a wonderful place. It was clean and spacious. It was well stocked. It even had bread and jam for us. It had a kitchen well-stocked with pots, pans, silverware and plates. The owner, Daniella, runs the clothing store in the same building and was very accessible and helpful. It is close by restaurants and shops and was even a nice sized Pam Local supermarket just a few doors away."
Charming apartment in the Historic Center of Siena
Volterra Countryside House
Fridge, microwave, oven, stovetop

Volterra Countryside House

9.6 out of 10, Exceptional, (14)
"Lots of room on 3 floors very close to all the sites"
Volterra Countryside House
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Outdoor dining

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Holiday house with private pool and fenced garden
A heated pool

Holiday house with private pool and fenced garden

10.0 out of 10, Exceptional, (49)
"We really enjoyed our 10 day stay, beds were comfortable and everything was clean, the pool was fantastic with an amazing view. Lots of space for two couples to relax and unwind yet within an hour of all the major towns and attractions. Jurgen was responsive to our needs and even helped us with the pizza oven. We will definitely consider staying here again."
Holiday house with private pool and fenced garden
Beautiful stone house with garden and private pool.
Property grounds

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.
Tuscan house in an ancient village near San Gimignano - Il Fienile
Pool

Tuscan house in an ancient village near San Gimignano - Il Fienile

9.8 out of 10, Exceptional, (51)
"Excellent and quick contact with property owner. She was very responsive when I had to make very rapid arrangements (less than 72 hours) after a different VRBO didn't work out. Upon our arrival, Roberto (the property manager - lovely gentleman - very prompt and responsive), helped us to understand the property and it's layout. We felt well-prepared and faced no difficulties during our stay. Roberto speaks Italian and English and we speak mostly English with just enough Italian to be...
Tuscan house in an ancient village near San Gimignano - Il Fienile
Detached villa with panoramic garden
Outdoor pool

Detached villa with panoramic garden

9.8 out of 10, Exceptional, (52)
"We had a great stay at the house of Marisa and Paolo. Both were very welcoming, and we spent a perfect week in Chiusdino. The house provided everything we needed for our family of four. From the garden we had a beautiful view towards the hills. And the swimming pool was great to cool down and escape from the summer heat. Chiusdino provides a couple of good restaurants which are all in walking distance. We usually had our morning coffee in the bellavista bar, which rightfully has this name. For...
Detached villa with panoramic garden
Le Macine, a wonderful ancient restored watermill with Pool
Pool

Le Macine, a wonderful ancient restored watermill with Pool

9.6 out of 10, Exceptional, (74)
"House was so cute, owner was there when we arrived and was very responsive to any questions. Great location to many of the surrounding towns."
Le Macine, a wonderful ancient restored watermill with Pool
detached villa with private pool and garden
Pool

detached villa with private pool and garden

8.8 out of 10, Excellent, (19)
"We loved this property- very well equipped, lovely pool and great views. And, only a few minutes walk into the village with lovely bars restaurants and shops. A perfect location. The only thing that might cause an issue for some ( not for us) , is that the third bedroom is a mezzanine floor within the second bedroom with a very steep staircase. The only access to the bathroom from these rooms is either through the main bedroom or through the patio door and around the outside of the property. ...
detached villa with private pool and garden
Charming ancient farm house in Chianti
Interior

Charming ancient farm house in Chianti

9.6 out of 10, Exceptional, (43)
"The primary reason for not recommending this property is due to our dealings with the host but there are other issues with the property. As has been said by other reviewers this property is very cluttered with very little space for renters to put any of their own things. The appliances are old, much of the china is chipped and we ended up buying our own pans rather than use the old aluminium ones in the property! The internet did not work at all for us, and Mariangela. who checked us in, told us...
Charming ancient farm house in 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
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (153)
"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 561
AED 633 total
includes taxes & fees
8 Apr - 9 Apr
Il Battistero Siena - Residenza d'Epoca
san gimignano apartment in historical center, courtyard and fast free wifi
Outdoor dining

san gimignano apartment in historical center, courtyard and fast free wifi

9.6 out of 10, Exceptional, (28)
"Amazing place with great location "
The price is AED 358
AED 569 total
includes taxes & fees
9 Apr - 10 Apr
san gimignano apartment in historical center, courtyard and fast free wifi
Riserva di Fizzano Residence
Outdoor pool, pool umbrellas, sun loungers

Riserva di Fizzano Residence

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay and experience. The property is well maintained and very peaceful. Everyone on the staff is friendly and very excited to have you as a guest. Food was wonderful. 5 stars all around. Convenient location for day trips or to just relax by the pool. Highly recommend"
Riserva di Fizzano Residence
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.