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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for San Gimignano villas

A stone building with a large glass door, a wooden deck, and a stone wall.

1. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is CA $7,899
CA $8,492 total
includes taxes & fees
Oct 12 - Oct 13
Villa "Arnilù" with Private Pool & Wi-Fi
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

2. 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 CA $231
CA $259 total
includes taxes & fees
Oct 6 - Oct 7
Villa Montecastello
A two-story building with a garden, a gazebo, and a statue.

3. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is CA $6,892
CA $6,897 total
includes taxes & fees
Oct 7 - Oct 8
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is CA $176
CA $210 total
includes taxes & fees
Oct 4 - Oct 5
Rooster House, cooking classes and opera
A covered balcony with a brick railing, a bench, and a view of lush greenery.

5. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is CA $737
CA $932 total
includes taxes & fees
Oct 4 - Oct 5
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A villa with a swimming pool, surrounded by lush greenery and hills.

6. Villa Belvedere with Private Pool and Volterra Views

Villa Belvedere with Private Pool and Volterra Views
Gambassi Terme
The price is CA $3,047
CA $3,052 total
includes taxes & fees
Oct 6 - Oct 7
Villa Belvedere with Private Pool and Volterra Views
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

7. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is CA $217
CA $310 total
includes taxes & fees
Oct 7 - Oct 8
Villa Le Polle di Meletro
A person in a swimming pool with a view of a vineyard and hills.

8. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveller
The price is CA $2,282
CA $2,969 total
includes taxes & fees
Oct 24 - Oct 25
"A Casa di Franca Villa con piscina"
A rural property with stone buildings, a garden, and a view of rolling hills.

9. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is CA $1,645
CA $1,802 total
includes taxes & fees
Oct 4 - Oct 5
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A building with a large entrance, potted plants, and a statue in the foreground.

10. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is CA $2,887
CA $2,890 total
includes taxes & fees
Nov 1 - Nov 2
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and vineyards.

11. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is CA $9,596
CA $9,602 total
includes taxes & fees
Oct 15 - Oct 16
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

12. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is CA $2,727
CA $3,121 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A two-story building with a red roof, multiple windows, and a gravel driveway.

13. Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is CA $2,264
CA $2,661 total
includes taxes & fees
Oct 6 - Oct 7
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

14. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is CA $2,647
CA $3,030 total
includes taxes & fees
Nov 1 - Nov 2
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

15. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is CA $321
CA $529 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
A stone building with a swimming pool, wooden deck, and a tall tree.

16. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is CA $1,800
CA $2,571 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A villa with a swimming pool, surrounded by lush greenery and hills.

17. Villa Linchiano with Private Pool for 11 Guests

Villa Linchiano with Private Pool for 11 Guests
Gambassi Terme
The price is CA $2,239
CA $2,244 total
includes taxes & fees
Oct 26 - Oct 27
Villa Linchiano with Private Pool for 11 Guests
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

18. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $20,835
CA $20,835 total
includes taxes & fees
Oct 6 - Oct 7
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

19. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is CA $10,418
CA $11,217 total
includes taxes & fees
Oct 7 - Oct 8
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

20. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is CA $2,212
CA $2,218 total
includes taxes & fees
Oct 4 - Oct 5
Molino In Chianti - Villa with Private Pool
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 San Gimignano Hotel Reviews

Hotel Leon Bianco

Hotel Leon Bianco

10/10 Excellent
"It was a joy to come back to San Gimignano and stay at Leon Bianco. I once stayed here as a child with my father on a trip and it was so nice to return again. Thank you to the family who keeps this hotel nice over the years, it is a historic building, right in Piazza Cisterna in the center of all. At night the town is beautiful. Short walk to the wall to see the view of Toscana countryside. Good breakfast and helpful staff to keep the luggage. Ciao Gimignano!"
Anthony 1-night trip
Posted 7 hours ago
Hotel Leon Bianco

Find out more about San Gimignano

San Gimignano Villas information

Number of reviews
214
Accommodation
67 Villas
Lowest Price
CA $210
Highest Price
CA $20,835

Frequently asked questions

How much do villas in San Gimignano cost?
Prices for villas in San Gimignano range between CA $210 and CA $20,835 per night. No matter your budget, you're sure to find a place that fits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in San Gimignano?
San Gimignano has 67 villas to pick from. Find a place that's perfect quickly and easily by checking the "Villa" box under the "Property type" tab in our filter tool.
Why book your villa in San Gimignano with Expedia?
Expedia makes it a breeze to find your dream villa in San Gimignano. Taking the kids on vacation? Use our filters to look for stays with amenities like WiFi and a pool. If you have a set budget, decide on how much you'd like to spend and the star rating of the property. We'll help you find a perfect place that matches your style and taste.
How can I find cheap villas in San Gimignano?
The best way to locate cheap villas in San Gimignano is with Expedia's user-friendly filter tool. Narrow your search by star rating, budget and amenities to grab unbeatable rates in just a couple of clicks.
What is there to do near my villa in San Gimignano?
There are loads of awesome things to do and see in San Gimignano. Don't miss leading attractions like Sant'Agostino Church, Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery and Tenuta Torciano Winery. Ornithological Museum, Historical Torture Museum and Torre Grossa are also on many to-do lists.

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