A city with historic towers and a vineyard.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Castel San Gimignano holiday rentals

A garden with a stone pathway, wooden benches, and various potted plants.

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (87 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ฿5,066
฿5,760 total
includes taxes & fees
28 Oct - 29 Oct
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ฿5,007
฿5,583 total
includes taxes & fees
25 Oct - 26 Oct
Palazzo Pacini
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

3. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is ฿3,081
฿3,577 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
An open wooden door leading to an outdoor patio with a table and chairs.

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is ฿3,064
฿4,497 total
includes taxes & fees
8 Nov - 9 Nov
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

5. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is ฿4,573
฿5,218 total
includes taxes & fees
18 Oct - 19 Oct
B&B Palazzo Tortoli
A narrow street with stone buildings, a tower, and an archway.

6. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is ฿3,534
฿4,075 total
includes taxes & fees
3 Nov - 4 Nov
Materia Rooms San Gimignano
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is ฿1,782
฿2,073 total
includes taxes & fees
13 Oct - 14 Oct
Camping Boschetto Di Piemma
A building with a wooden door, windows with shutters, and flower boxes.

8. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is ฿2,561
฿3,004 total
includes taxes & fees
1 Nov - 2 Nov
Donna Nobile
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

9. Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is ฿3,534
฿4,075 total
includes taxes & fees
18 Oct - 19 Oct
Affittacamere Le Ginestre
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

10. Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is ฿4,302
฿4,845 total
includes taxes & fees
19 Oct - 20 Oct
Tenuta Quadrifoglio
A stone building with outdoor seating and a view of the countryside.

11. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ฿5,685
฿6,366 total
includes taxes & fees
14 Oct - 15 Oct
Antico Borgo Poggiarello
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

12. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is ฿3,535
฿4,002 total
includes taxes & fees
1 Nov - 2 Nov
Tenuta Sant'Ilario
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

13. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Lovely stay at a little gem in Volterra. Enrico the owner has created a great concept with different apartments around the city and the restaurant is serving delicious local plant based food. Don’t miss the cheesecake ❤️"
Sweden
Mia
The price is ฿4,003
฿5,681 total
includes taxes & fees
13 Oct - 14 Oct
AlbergoDiffusoVolterra
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

14. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿5,811
฿6,467 total
includes taxes & fees
19 Oct - 20 Oct
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

Hotel Italia

Hotel Italia

10/10 Excellent
"Staff and hotel was great."
Suzanne 1-night trip
Posted 8 hours ago
Hotel Italia

Find out more about Castel San Gimignano

Search for holiday rentals in Castel San Gimignano on Expedia! You can easily find your home rentals, villas, holiday apartments in Castel San Gimignano using one of the methods below:

  • View our selection of featured holiday rentals in Castel San Gimignano
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Look no further and take a look at our great range of rental properties in Castel San Gimignano!

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 Val di Merse. In the wider area, you’ll find Sovestro in Poggio Winery and Casa e Torre Campatelli.

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.