A city with historic towers and a vineyard.

Holiday Rentals in Castel San Gimignano

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castel San Gimignano holiday rentals

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is €116
includes taxes & fees
10 Dec - 11 Dec
Palazzo Pacini
An open wooden door leading to an outdoor patio with a table and chairs.

2. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Very friendly host 🙌 and great location"
Denmark
Klaus
The price is €123
includes taxes & fees
14 Nov - 15 Nov
Palazzo al Torrione 2
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

3. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 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 €91
includes taxes & fees
12 Nov - 13 Nov
Casa Vacanze Le Case
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, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is €108
includes taxes & fees
1 Dec - 2 Dec
B&B Palazzo Tortoli
A historic stone building with a prominent tower, arched windows, and a tiled roof.

5. 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 €109
includes taxes & fees
12 Nov - 13 Nov
Materia Rooms San Gimignano
A building with a wooden door, windows with shutters, and flower boxes.

6. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is €80
includes taxes & fees
8 Dec - 9 Dec
Donna Nobile
A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

7. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is €49
includes taxes & fees
15 Nov - 16 Nov
Sportland
A narrow alleyway with brick walls, wooden barrels, and potted plants.

8. Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.

Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.
San Gimignano City Centre
9.8 out of 10, Exceptional, (44 reviews)
"P. Buonaccorsi is a unique property that is centrally located in San Gimignano. It is well maintained and restored and a very beautiful residence. Senora and Bianca were perfect hosts. The town was perfectly located in Tuscany and within easy day-trips to Florence, Siena, and Massa Marittima."
United States
Glenn
The price is €148
includes taxes & fees
12 Nov - 13 Nov
Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

9. 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 €109
includes taxes & fees
12 Nov - 13 Nov
Affittacamere Le Ginestre
A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

10. 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 €129
includes taxes & fees
12 Nov - 13 Nov
Tenuta Quadrifoglio
A vineyard with a stone building, a metal gate, and purple plants in the foreground.

11. 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, (17 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
The price is €250
includes taxes & fees
12 Nov - 13 Nov
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

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 €166
includes taxes & fees
12 Nov - 13 Nov
AlbergoDiffusoVolterra
An ancient stone structure with a central archway, surrounded by a cobblestone plaza and historic buildings in the background.

13. Apartment in San Gimignano in the heart of the city for 3 people: fast Wi-Fi, concierge service.

Apartment in San Gimignano 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)
"Beautiful bit of Italian history! Bianca was a gracious very helpful asset to the charming accommodation."
United States
Julie B.
The price is €209
includes taxes & fees
12 Nov - 13 Nov
Apartment in San Gimignano in the heart of the city for 3 people: fast Wi-Fi, concierge service.
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

14. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
9.6 out of 10, Exceptional, (5 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
Borgo Antico Residence
A modern bedroom with a bed, bedside tables, a bench, and artwork on the wall.

15. Vale's House

Vale's House
Certaldo
The price is €137
includes taxes & fees
10 Dec - 11 Dec
Vale's House
A kitchen with a brick wall, modern appliances, and an arched doorway leading to a dining area.

16. Casa Masoni – Your Elegant and Welcoming Home in Tuscany

Casa Masoni – Your Elegant and Welcoming Home in Tuscany
Colle val d'Elsa
9.8 out of 10, Exceptional, (9 reviews)
"Very close from Siena, San Gimignano and Chianti and Colle Val d' Elsa alta a really nice village to visit. 15' walking from the house. Deanna is a perfect anfitriona helping with everything for your stay."
Spain
Jorge S.
The price is €304
includes taxes & fees
13 Nov - 14 Nov
Casa Masoni – Your Elegant and Welcoming Home in Tuscany
An outdoor patio with a round wooden table, a wicker chair, and a potted plant.

17. Casa Bardi: Superior Apartment with Sauna + Parking

Casa Bardi: Superior Apartment with Sauna + Parking
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Of all the places we have stayed, this is by far the best experience ever. Diego was communicative from the start, provided loads of information about the village; reccomendations on where to eat, what to do…. What really impressed us was his attentiveness and care for our comfort and the San Gimignano experience. He met us near the condo and guided us to a safe, private, free parking spot a very short distance to our beautiful “rustic” condo, inside the outer walls of San Gimignano we had a...
United States
LESLIE P.
The price is €287
includes taxes & fees
17 Nov - 18 Nov
Casa Bardi: Superior Apartment with Sauna + Parking
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

18. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is €109
includes taxes & fees
1 Dec - 2 Dec
Antica Pieve B&B
A two-story stone house with a swimming pool, surrounded by greenery and a clear sky.

19. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
9.8 out of 10, Exceptional, (10 reviews)
"Tutto perfetto: accoglienza, pulizia, bellezza. Proprietari gentilissimi. Un luogo che resta nel cuore. Ci ritorneremo.."
Italy
giuseppe z.
The price is €233
includes taxes & fees
12 Nov - 13 Nov
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
A table with breakfast items and a view of rolling hills.

20. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is €73
includes taxes & fees
15 Nov - 16 Nov
Chianti Village Morrocco
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

Palazzo Ravizza

Palazzo Ravizza

8/10 Good
"Convenient place to stay with car to tour Tuscany. Breakfast was good. Room cleaned daily. Charming old building. Hotel works closely with you to navigate the ZTL; you need to be able to walk up some stairs from car park down the hill after dropping your bags at the main door. Away from the bustle around the piazzas: quiet. You need to not mind walking up and down hills to enjoy Siena and most of the historic towns in Tuscany. Staff at front desk fluent in English."
Mark 3-night trip
Posted 14 hours ago
Palazzo Ravizza

Find out more about Castel San Gimignano

Everything you need to know about Castel San Gimignano holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castel San Gimignano holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castel San Gimignano holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castel San Gimignano holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castel San Gimignano holiday rentals we have selected for you start as low as €65 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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. 

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.

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

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

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.