Search Vacation Homes in Castel San Gimignano

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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 1145 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)
Holiday home in the Florentine Chianti half an hour from Florence
Interior

Holiday home in the Florentine Chianti half an hour from Florence

9.8 out of 10, Exceptional, (53)
"Montespertoli did not disappoint. This home is very well located to enjoy a small town and have easy access to other small towns, as well as Florence and Lucca-two of our favorites. Wine tasting, gelato, bakery, groceries, post office all within a short walk. The listing was accurate and our family of six had plenty of room to be together or find a quiet space. We especially enjoyed the rooftop patio. Bruno was responsive to questions and recommendations and the check in/check out process was...
Holiday home in the Florentine Chianti half an hour from Florence
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.
Independent house in the hills of the Sienese countryside
Exterior

Independent house in the hills of the Sienese countryside

10.0 out of 10, Exceptional, (73)
"The picture of the farmhouse doesn't do the location justice after you see it in person.. it's a spectacular view! We arrived on a beautiful sunny day and were warmly welcomed by our hosts. After getting a quick tour of where we would be staying for the next week, we were pleasantly surprised by the kind gesture of homemade olive oil and wine left for us to have. Thank you! The location of this property is perfect for visiting the Tuscany countryside. Not only did we visit Siena on a few...
Independent house in the hills of the Sienese countryside
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
The Photographer's House
Point of interest

The Photographer's House

9.8 out of 10, Exceptional, (9)
"The house is spacious, interesting and has everything needed for a holiday. The garden is a huge bonus - room to relax with a view (and grapes on the vine!). It was a joy to stay in an historic house in such an interesting town, with shops and restaurants within easy walking distance. We had a delicious meal at the owner’s restaurant too."
The Photographer's House
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 SAR 669
SAR 900 total
includes taxes & fees
27 Mar - 28 Mar
Chianti Craft House Badia a Passignano
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Point of interest

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (17)
"Beautiful, comfortable and spacious apartment. Very central - so close to Il Campo and the Duomo and restaurants and cafes. Great communications. Good facilities. Fab air conditioning which we really needed. Only issue was the back shower which trickled from the top shower but the other shower was decent. We had a lovely stay at Palazzo Nannini and look forward to returning. Highly recommend."
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
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
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. "
Casa Vacanze Le Case
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
A wonderful country house in the heart of Chianti
Terrace/patio

A wonderful country house in the heart of Chianti

9.8 out of 10, Exceptional, (21)
"Beds need to be looked at"
A wonderful country house in the heart of Chianti
House in a typical village in the heart of Chianti
Pool

House in a typical village in the heart of Chianti

9.6 out of 10, Exceptional, (68)
"Our 2 bedroom apartment was beautiful in every way. Perfect location, accommodations, and atmosphere for a 5 day holiday away from crowds. We loved it. The owners were friendly and helpful."
House in a typical village in the heart of Chianti
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
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
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
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)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is SAR 554
SAR 625 total
includes taxes & fees
27 Mar - 28 Mar
Il Battistero Siena - Residenza d'Epoca
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
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 SAR 288
SAR 502 total
includes taxes & fees
27 Mar - 28 Mar
san gimignano apartment in historical center, courtyard and fast free wifi
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.