A city with historic towers and a vineyard.

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Castel San Gimignano holiday rentals

Exterior

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.726.921 ₫
5.352.094 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino
Terrace/patio

2. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is 2.948.946 ₫
3.304.874 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini
Superior Mobile Home | Terrace/patio

3. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (88 reviews)
The price is 1.372.332 ₫
1.601.054 ₫ total
includes taxes & fees
25 Sept - 26 Sept
Camping Boschetto Di Piemma
La Torre Grossa

4. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is 2.946.178 ₫
3.393.379 ₫ total
includes taxes & fees
18 Sept - 19 Sept
Materia Rooms San Gimignano
Balcony

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (112 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is 2.862.778 ₫
4.063.943 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Palazzo al Torrione 2
Porch

6. 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 2.413.569 ₫
2.807.540 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Donna Nobile
Pool

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is 3.423.815 ₫
3.918.769 ₫ total
includes taxes & fees
25 Sept - 26 Sept
Casa Vacanze Le Case
Family Apartment, 5 Bedrooms, Garden View, Garden Area (10 people) | Terrace/patio

8. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is 5.728.297 ₫
6.453.680 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Borgo al Cerro
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

9. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 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 3.795.172 ₫
4.327.274 ₫ total
includes taxes & fees
27 Aug - 28 Aug
B&B Palazzo Tortoli
Garden view

10. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (49 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is 2.119.213 ₫
2.514.112 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Villa San Filippo
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio

11. 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 3.302.050 ₫
3.784.839 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Affittacamere Le Ginestre
Casa Alberi - Albergo Diffuso Volterra

12. 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 3.098.060 ₫
4.445.435 ₫ total
includes taxes & fees
28 Aug - 29 Aug
AlbergoDiffusoVolterra
Villa, Air conditioning, Courtyard View | Exterior

13. 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 5.053.572 ₫
5.650.480 ₫ total
includes taxes & fees
29 Aug - 30 Aug
Villa Montecastello
Front of property

14. 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 1.737.677 ₫
2.765.914 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Borgo Antico Residence
Garden

15. 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 3.911.636 ₫
4.394.411 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Tenuta Quadrifoglio
Deluxe Room, Patio

16. 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 3.663.229 ₫
4.120.980 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Tenuta Sant'Ilario
Food court

17. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is 4.157.213 ₫
6.739.622 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Borgo Il Poggiaccio
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

Poderi Arcangelo

Poderi Arcangelo

10/10 Excellent
"This is a beautiful place to stay. The pool is wonderful and the breakfast is delicious. The views are outstanding. The only thing I would suggest for our 4 person room is to put a second mirror in the room, outside of the bathroom. That would have made a big difference to 4 people sharing a bathroom."
Lisa 3-night trip
Posted 20 hours ago
Poderi Arcangelo

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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 Alta Val d'Elsa River Park. 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.