A city with historic towers and a vineyard.

Castel San Gimignano Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Castel San Gimignano vacation rentals

A garden with a stone pathway, wooden benches, and various potted plants.

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (88 reviews)
"friendly staff, gorgeous property"
United States
Heidi
$133 nightly
The price is $151
Oct 25 - Oct 26
Total with taxes and fees
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$149 nightly
The price is $167
Oct 25 - Oct 26
Total with taxes and fees
Palazzo Pacini
A view from a window overlooking a rural landscape with fields and a distant mountain range.

3. 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
$123 nightly
The price is $141
Nov 4 - Nov 5
Total with taxes and fees
B&B Palazzo Tortoli
A narrow street with stone buildings, a tower, and an archway.

4. 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
$104 nightly
The price is $120
Nov 23 - Nov 24
Total with taxes and fees
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$117 nightly
The price is $134
Nov 7 - Nov 8
Total with taxes and fees
Palazzo al Torrione 2
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

6. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$47 nightly
The price is $55
Oct 25 - Oct 26
Total with taxes and fees
Camping Boschetto Di Piemma
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

7. 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
$90 nightly
The price is $105
Nov 2 - Nov 3
Total with taxes and fees
Casa Vacanze Le Case
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

8. 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
$97 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
Affittacamere Le Ginestre
A reception desk with the word "SPORTLAND" prominently displayed.

9. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
$45 nightly
The price is $51
Oct 25 - Oct 26
Total with taxes and fees
Sportland
A building with a wooden door, windows with shutters, and flower boxes.

10. 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
$79 nightly
The price is $93
Nov 2 - Nov 3
Total with taxes and fees
Donna Nobile
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

11. 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
$128 nightly
The price is $145
Oct 25 - Oct 26
Total with taxes and fees
Tenuta Quadrifoglio
A stone building with outdoor seating and a view of the countryside.

12. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
Antico Borgo Poggiarello
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

13. 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
$161 nightly
The price is $178
Nov 6 - Nov 7
Total with taxes and fees
AlbergoDiffusoVolterra
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

14. 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
$97 nightly
The price is $110
Nov 3 - Nov 4
Total with taxes and fees
Tenuta Sant'Ilario
Living area

15. La Rocca Romantica

La Rocca Romantica
San Gimignano City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment with unbeatable location. in few steps up will take you to a nearby fortress and great view of the countryside and few steps down take you to the main plaza. hosts were also very friendly and helpful and available to help when needed."
United States
Sinava
$122 nightly
The price is $140
Nov 5 - Nov 6
Total with taxes and fees
La Rocca Romantica
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

16. 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
$178 nightly
The price is $200
Oct 27 - Oct 28
Total with taxes and fees
Villa Montecastello
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

17. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$72 nightly
The price is $83
Nov 20 - Nov 21
Total with taxes and fees
Tuscasì Aparthotel
A table set with breakfast items on a balcony overlooking a historic town.

18. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
$141 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

19. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
$103 nightly
The price is $118
Nov 9 - Nov 10
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

20. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$84 nightly
The price is $99
Oct 28 - Oct 29
Total with taxes and fees
Villa San Filippo
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

NH Siena

NH Siena

10/10 Excellent
"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"
Rakhshan 1-night trip
Posted 11 hours ago
NH Siena

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 $55 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 Val di Merse. 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.