A city with historic towers and a vineyard.

Castel San Gimignano Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$145 nightly
The price is $165
Oct 4 - Oct 5
Total with taxes and fees
Antico Borgo il Cardino
Property grounds

2. Giovanna apartment on two levels overlooking the swimming pool

Giovanna apartment on two levels overlooking the swimming pool
Castel San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect - the best is this wonderful Garden with the views in the toscana"
Germany
Antje F.
Giovanna apartment on two levels overlooking the swimming pool
Terrace/patio

3. 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
$138 nightly
The price is $154
Oct 8 - Oct 9
Total with taxes and fees
Palazzo Pacini
Superior Mobile Home | Terrace/patio

4. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$46 nightly
The price is $54
Sep 15 - Sep 16
Total with taxes and fees
Camping Boschetto Di Piemma
Porch

5. 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
$88 nightly
The price is $102
Sep 10 - Sep 11
Total with taxes and fees
Donna Nobile
Balcony

6. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (112 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
$134 nightly
The price is $154
Sep 20 - Sep 21
Total with taxes and fees
Palazzo al Torrione 2
La Torre Grossa

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
Materia Rooms San Gimignano
Pool

8. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
$131 nightly
The price is $149
Sep 20 - Sep 21
Total with taxes and fees
Casa Vacanze Le Case
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
$152 nightly
The price is $173
Sep 15 - Sep 16
Total with taxes and fees
B&B Palazzo Tortoli
Property grounds

10. 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, (16 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
$269 nightly
The price is $298
Sep 19 - Sep 20
Total with taxes and fees
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
Villa, Air conditioning, Courtyard View | Exterior

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
$172 nightly
The price is $192
Sep 19 - Sep 20
Total with taxes and fees
Villa Montecastello
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio

12. 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
$122 nightly
The price is $140
Sep 16 - Sep 17
Total with taxes and fees
Affittacamere Le Ginestre
Property grounds

13. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
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.
$187 nightly
The price is $193
Oct 9 - Oct 10
Total with taxes and fees
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
Outdoor dining

14. San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (12 reviews)
"Our cosy little part of the palazzo was wonderful and our host sent us to an amazing array of restaurants. We had a wonderful time."
United States
Daniel T.
$244 nightly
The price is $250
Sep 10 - Sep 11
Total with taxes and fees
San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service
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
$149 nightly
The price is $167
Sep 14 - Sep 15
Total with taxes and fees
Tenuta Quadrifoglio
Interior

16. 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.
$420 nightly
The price is $422
Sep 12 - Sep 13
Total with taxes and fees
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Garden view

17. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.8 out of 10, Excellent, (52 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$133 nightly
The price is $153
Oct 4 - Oct 5
Total with taxes and fees
Villa San Filippo
Casa Alberi - Albergo Diffuso Volterra

18. 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
$154 nightly
The price is $170
Oct 1 - Oct 2
Total with taxes and fees
AlbergoDiffusoVolterra
Deluxe Room, Patio

19. 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
$144 nightly
The price is $161
Sep 29 - Sep 30
Total with taxes and fees
Tenuta Sant'Ilario
Food court

20. 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
$135 nightly
The price is $154
Sep 29 - Sep 30
Total with taxes and fees
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The staff were very friendly and helpful. The bar service is the best."
Harley 1-night trip
Posted 6 hours ago
Villa Scacciapensieri Boutique Hotel

Find out more about Castel San Gimignano

Everything you need to know about Castel San Gimignano vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castel San Gimignano vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castel San Gimignano vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castel San Gimignano vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castel San Gimignano. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castel San Gimignano in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $54 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castel San Gimignano rentals

At Expedia, we put the best Castel San Gimignano vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castel San Gimignano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castel San Gimignano vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castel San Gimignano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Villa with large garden in the Chianti hills: This vacation home rental outside of Castel San Gimignano is located in a rural location and has an outdoor pool, a fireplace, 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. You can relax into your vacation with a garden and a selection of books.

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.