A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

San Gimignano Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for San Gimignano holiday rentals

1. 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 NZ$239
includes taxes & fees
6 Oct - 7 Oct
Materia Rooms San Gimignano

2. 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 NZ$268
includes taxes & fees
29 Sept - 30 Sept
Palazzo al Torrione 2

3. 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.
The price is NZ$336
includes taxes & fees
19 Oct - 20 Oct
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

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 NZ$269
includes taxes & fees
20 Oct - 21 Oct
B&B Palazzo Tortoli

5. 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 traveller
The price is NZ$101
includes taxes & fees
1 Oct - 2 Oct
Camping Boschetto Di Piemma

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 NZ$177
includes taxes & fees
4 Oct - 5 Oct
Donna Nobile

7. 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 NZ$208
includes taxes & fees
19 Oct - 20 Oct
Affittacamere Le Ginestre

8. 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
The price is NZ$516
includes taxes & fees
29 Sept - 30 Sept
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

9. La Rocca Romantica

La Rocca Romantica
San Gimignano City Centre
The price is NZ$261
includes taxes & fees
11 Oct - 12 Oct
La Rocca Romantica

10. 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 NZ$285
includes taxes & fees
13 Oct - 14 Oct
Antico Borgo il Cardino

11. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is NZ$251
includes taxes & fees
4 Oct - 5 Oct
Casa Vacanze Le Case

12. 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.
The price is NZ$433
includes taxes & fees
29 Sept - 30 Sept
San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

13. IL VECCHIO CONVENTO

IL VECCHIO CONVENTO
San Gimignano City Centre
4.0 out of 10, (3 reviews)
"Unterkunft konnte wegen Wasserschaden nicht bezogen werden. Vermieter hat nicht geholfen eine Alternative zu finden…"
Germany
Bodo
The price is NZ$294
includes taxes & fees
1 Oct - 2 Oct
IL VECCHIO CONVENTO

14. ONE-ROOM FLAT 3 KM FROM SAN GIMIGNANO

ONE-ROOM FLAT 3 KM FROM SAN GIMIGNANO
San Gimignano
The price is NZ$163
includes taxes & fees
29 Sept - 30 Sept
ONE-ROOM FLAT 3 KM FROM SAN GIMIGNANO

15. Cozy double room with bathroom in the historic center of San Gimignano.

Cozy double room with bathroom in the historic center of San Gimignano.
San Gimignano City Centre
The price is NZ$298
includes taxes & fees
29 Sept - 30 Sept
Cozy double room with bathroom in the historic center of San Gimignano.

16. Nuovissimo Appartamento Appena Fuori Dalle Antiche Mura di SAN Gimignano,

Nuovissimo Appartamento Appena Fuori Dalle Antiche Mura di SAN Gimignano,
San Gimignano
The price is NZ$232
includes taxes & fees
5 Oct - 6 Oct
Nuovissimo Appartamento Appena Fuori Dalle Antiche Mura di SAN Gimignano,

17. THE OLD CONVENT

THE OLD CONVENT
San Gimignano City Centre
The price is NZ$298
includes taxes & fees
29 Sept - 30 Sept
THE OLD CONVENT

18. I'Quercecchio Relax with Sauna - In the Historic Center of SamGimignano

I'Quercecchio Relax with Sauna - In the Historic Center of SamGimignano
San Gimignano City Centre
6.0 out of 10, (3 reviews)
"We did not even get the room we booked. Bait and switch. Owner tried to put us in another dirty, smelly, apartment not near where we booked. Terrible experience. I would not trust them at all!"
United States
Gary
The price is NZ$318
includes taxes & fees
29 Sept - 30 Sept
I'Quercecchio Relax with Sauna - In the Historic Center of SamGimignano

19. IL CASTAGNOLO COUNTRY B&B Torre Becci

IL CASTAGNOLO COUNTRY B&B Torre Becci
San Gimignano
IL CASTAGNOLO COUNTRY B&B Torre Becci

20. Il CASTAGNOLO COUNTRY B&B Torre Pesciolini

Il CASTAGNOLO COUNTRY B&B Torre Pesciolini
San Gimignano
Il CASTAGNOLO COUNTRY B&B Torre Pesciolini
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Gimignano Hotel Reviews

Find out more about San Gimignano

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Gimignano holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Gimignano. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Gimignano. Seeing all the best attractions is bound to make you fall in love with San Gimignano. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Gimignano short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in San Gimignano?

Yes, there are holiday rentals close to the most popular sights in San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to San Gimignano speak positively about the beautiful countryside and wineries in this destination. Make sure you have time to check out the museums and cafés during your trip.

What are some of the best holiday rentals that San Gimignano has to offer?

Casa Vacanze Le Case: This highly rated holiday home rental in San Gimignano offers an outdoor pool, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a stovetop and kitchenware can make your holiday run smoothly. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in San Gimignano?

With 60 Expedia holiday rentals, you're guaranteed to find just the right place for your San Gimignano stay.

What’s there to see and do in San Gimignano?

Cultural attractions include San Gimignano Communal Palace and Medieval Criminal and Torture Museum, whereas Castelvecchio Natural Reserve is one spot to enjoy nature. Other places in town to visit include Piazza della Cisterna and Torre Grossa.

What’s a holiday rental in San Gimignano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Gimignano. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.