A city with historic towers and a vineyard.

Castel San Gimignano Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is S$204
includes taxes & fees
13 Oct - 14 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 S$190
includes taxes & fees
3 Nov - 4 Nov
Palazzo Pacini
An open wooden door leading to an outdoor patio with a table and chairs.

3. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 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 S$192
includes taxes & fees
8 Oct - 9 Oct
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

4. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 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 S$184
includes taxes & fees
7 Oct - 8 Oct
B&B Palazzo Tortoli
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

5. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (90 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is S$72
includes taxes & fees
6 Oct - 7 Oct
Camping Boschetto Di Piemma
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

6. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 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 S$133
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A narrow street with stone buildings, a tower, and an archway.

7. 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 S$155
includes taxes & fees
3 Nov - 4 Nov
Materia Rooms San Gimignano
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, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is S$115
includes taxes & fees
1 Nov - 2 Nov
Donna Nobile
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

9. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is S$130
includes taxes & fees
11 Oct - 12 Oct
Borgo Antico Residence
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

10. 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 S$147
includes taxes & fees
20 Oct - 21 Oct
Affittacamere Le Ginestre
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

11. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is S$240
includes taxes & fees
6 Oct - 7 Oct
Villa Montecastello
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 S$144
includes taxes & fees
1 Nov - 2 Nov
Tenuta Sant'Ilario
A stone building with outdoor seating and a view of the countryside.

13. 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 S$220
includes taxes & fees
11 Oct - 12 Oct
Antico Borgo Poggiarello
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, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is S$260
includes taxes & fees
6 Oct - 7 Oct
Riserva di Fizzano Residence
Living area

15. La Rocca Romantica

La Rocca Romantica
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Very nice apartment with unbeatable location. in few steps up will take you to a nearby fortress and great view of the countryside and few steps down take you to the main plaza. hosts were also very friendly and helpful and available to help when needed."
United States
Sinava
The price is S$211
includes taxes & fees
9 Oct - 10 Oct
La Rocca Romantica
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

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Property was beautiful staff was great last time with my family"
Niurka 3-night trip
Posted 4 hours ago
Salvadonica - Borgo del Chianti

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.