A city with historic towers and a vineyard.

Castel San Gimignano Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Castel San Gimignano vacation rentals

Exterior

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ￥26,793
￥30,391 total
includes taxes & fees
Sep 6 - Sep 7
Antico Borgo il Cardino
Property grounds

2. Edera cozy house in Tuscan village

Edera cozy house in Tuscan village
Castel San Gimignano
Edera cozy house in Tuscan village
Property grounds

3. Double bedroom loggia overlooking the pool

Double bedroom loggia overlooking the pool
Castel San Gimignano
Double bedroom loggia overlooking the pool
Terrace/patio

4. 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 ￥17,998
￥20,166 total
includes taxes & fees
Sep 2 - Sep 3
Palazzo Pacini
Balcony

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ￥17,221
￥24,459 total
includes taxes & fees
Sep 14 - Sep 15
Palazzo al Torrione 2
Family Apartment, 5 Bedrooms, Garden View, Garden Area (10 people) | Terrace/patio

6. 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 ￥34,173
￥38,509 total
includes taxes & fees
Sep 4 - Sep 5
Borgo al Cerro
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

7. 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 ￥30,040
￥33,963 total
includes taxes & fees
Aug 27 - Aug 28
B&B Palazzo Tortoli
Outdoor pool

8. 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 ￥19,418
￥22,279 total
includes taxes & fees
Aug 28 - Aug 29
Casa Vacanze Le Case
Villa, Air conditioning, Courtyard View | Exterior

9. 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 ￥30,452
￥34,049 total
includes taxes & fees
Aug 16 - Aug 17
Villa Montecastello
Outdoor dining

10. Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Colle Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"Schöne Zimmer, Dusche sehr modern und sehr sauber, Fernseher mit Internet-Anschluss sehr gut"
Germany
Rupert H.
The price is ￥66,605
￥74,823 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Property grounds

11. san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is ￥19,695
￥29,625 total
includes taxes & fees
Aug 15 - Aug 16
san gimignano apartment in historical center, courtyard and fast free wifi
La Torre Grossa | In-room safe, desk, laptop workspace, WiFi (free)

12. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is ￥19,331
￥22,183 total
includes taxes & fees
Aug 18 - Aug 19
Materia Rooms San Gimignano
Interior

13. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is ￥42,295
￥67,672 total
includes taxes & fees
Sep 12 - Sep 13
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Porch

14. 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 ￥13,363
￥15,618 total
includes taxes & fees
Aug 15 - Aug 16
Donna Nobile
Superior Mobile Home | Terrace/patio

15. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (88 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is ￥7,689
￥9,009 total
includes taxes & fees
Sep 9 - Sep 10
Camping Boschetto Di Piemma
Aerial view

16. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ￥31,911
￥35,470 total
includes taxes & fees
Sep 8 - Sep 9
Riserva di Fizzano Residence
Property grounds

17. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
San Gimignano City Centre
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
The price is ￥21,497
￥47,172 total
includes taxes & fees
Aug 20 - Aug 21
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
Garden view

18. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (47 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ￥17,343
￥20,180 total
includes taxes & fees
Sep 7 - Sep 8
Villa San Filippo
Property grounds

19. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
The price is ￥49,650
￥71,901 total
includes taxes & fees
Aug 15 - Aug 16
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
1 bedroom

20. Casa Vacanze Etrusco – Leccio Apartment

Casa Vacanze Etrusco – Leccio Apartment
San Gimignano
The price is ￥35,792
￥36,711 total
includes taxes & fees
Aug 20 - Aug 21
Casa Vacanze Etrusco – Leccio Apartment
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 Chiusarelli

Hotel Chiusarelli

8/10 Good
"It’s a nice enough property, but certainly not four or five star. I did enjoy my stay. The staff were phenomenal. The room was fine. I only was there for one night. The breakfast was so no food at all."
Joseph 1-night trip
Posted 13 hours ago
Hotel Chiusarelli

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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  • Enter your travel dates to view the best deals on holiday rentals in Castel San Gimignano while they last

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 vacation rental in Castel San Gimignano?

Yes, we have vacation rentals close to top local attractions 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 coffeehouses and local tours. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation rentals in Castel San Gimignano?

Holiday house with private pool and fenced garden: This vacation home rental outside of Castel San Gimignano is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Sovestro in Poggio Winery and Casa e Torre Campatelli.

What are vacation rentals like in Castel San Gimignano?

Vacation rentals are privately owned accommodations you can book for several days or more in Castel San Gimignano. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.