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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Castel San Gimignano holiday rentals

Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.290.717 ₫
4.873.029 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Antico Borgo il Cardino
Garden

Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (17 reviews)
"Wonderful and unique place to stay. Staff were terrific. The church bells ring through the night so bring earplugs if you’re a light sleeper!"
Canada
Brendan
The price is 1.873.454 ₫
2.183.651 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Antica Dimora Leones
Free WiFi

Casa di Alice

Casa di Alice
Barberino Tavarnelle
8.0 out of 10, Very good, (1 review)
"Very good "
Canada
richard
The price is 2.786.207 ₫
3.187.420 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Casa di Alice
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is 2.953.907 ₫
3.371.890 ₫ total
includes taxes & fees
13 Jun - 14 Jun
Il Pozzo di Sant'Andrea
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.314.206 ₫
2.944.051 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Tuscasì Aparthotel
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is 5.075.305 ₫
5.674.780 ₫ total
includes taxes & fees
2 Jun - 3 Jun
Villa Montecastello
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is 3.385.208 ₫
3.815.673 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Casa di Campagna in Toscana
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is 4.540.358 ₫
5.055.689 ₫ total
includes taxes & fees
28 May - 29 May
Palazzo Pacini
Seasonal outdoor pool, pool umbrellas, pool loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (42 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
The price is 1.927.103 ₫
2.303.701 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Villa San Filippo
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is 2.911.558 ₫
3.325.306 ₫ total
includes taxes & fees
28 May - 29 May
Fullino Nero
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is 2.359.114 ₫
2.656.322 ₫ total
includes taxes & fees
29 May - 30 May
Chianti Village Morrocco
Seasonal outdoor pool, pool loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is 4.102.649 ₫
4.604.858 ₫ total
includes taxes & fees
28 May - 29 May
Residence Arianna
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is 4.682.716 ₫
5.273.655 ₫ total
includes taxes & fees
9 Jun - 10 Jun
La Coroncina Lodging
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is 3.678.983 ₫
4.138.703 ₫ total
includes taxes & fees
18 Jun - 19 Jun
Tenuta Sant'Ilario
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (244 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is 3.639.726 ₫
4.126.291 ₫ total
includes taxes & fees
11 Jun - 12 Jun
La Terrazza Sul Campo Rooming House
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (31 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is 6.516.986 ₫
7.229.858 ₫ total
includes taxes & fees
27 Jun - 28 Jun
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.
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Top Castel San Gimignano Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"Lovely old hotel with a lot of character. Beautiful grounds and an excellent restaurant. We had a lovely stay here."
David 1-night trip
Posted 1 hour ago
Villa Scacciapensieri Boutique Hotel

Frequently asked questions

Can I find a holiday rental in Castel San Gimignano?

Yes, there are holiday rentals close to the most popular sights in Castel San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Castel San Gimignano is known for its coffee shops and local tours. Make sure you have time to check out the wineries while you're in the area.

How many holiday rentals will I find in Castel San Gimignano?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Castel San Gimignano stay.

What can I see and do in Castel San Gimignano?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Castelvecchio Natural Reserve. In the wider area, you’ll find Sovestro in Poggio Winery and Piazza della Cisterna.

What are holiday rentals like in Castel San Gimignano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castel San Gimignano. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for families.