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

Our top choices for San Gimignano villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. 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 NZ$359
includes taxes & fees
25 Oct - 26 Oct
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is NZ$259
includes taxes & fees
22 Nov - 23 Nov
Rooster House, cooking classes and opera
A covered balcony with a brick railing, a bench, and a view of lush greenery.

3. 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 NZ$1,153
includes taxes & fees
23 Oct - 24 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A person in a swimming pool with a view of a vineyard and hills.

4. "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 NZ$3,015
includes taxes & fees
22 Nov - 23 Nov
"A Casa di Franca Villa con piscina"
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

5. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is NZ$372
includes taxes & fees
3 Nov - 4 Nov
Villa Le Polle di Meletro
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

6. 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 NZ$3,575
includes taxes & fees
3 Nov - 4 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A building with a large entrance, potted plants, and a statue in the foreground.

7. 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 NZ$3,202
includes taxes & fees
1 Nov - 2 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

8. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
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 NZ$3,477
includes taxes & fees
1 Nov - 2 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A villa with a swimming pool, surrounded by lush greenery and vineyards.

9. 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 NZ$10,687
includes taxes & fees
25 Oct - 26 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A rural property with stone buildings, a garden, and a view of rolling hills.

10. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is NZ$4,940
includes taxes & fees
23 Oct - 24 Oct
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A stone building with a swimming pool, wooden deck, and a tall tree.

11. 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 NZ$2,948
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 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 NZ$651
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

13. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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 NZ$13,870
includes taxes & fees
23 Oct - 24 Oct
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A courtyard with a building, potted plants, and a grassy area.

14. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is NZ$4,212
includes taxes & fees
1 Nov - 2 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A modern poolside area with a clear view of the landscape.

15. Aureva Tuscany, modern villa with private pool

Aureva Tuscany, modern villa with private pool
Montelupo F.no
The price is NZ$1,164
includes taxes & fees
1 Nov - 2 Nov
Aureva Tuscany, modern villa with private pool
A table set for tea with a view of a garden and hills.

16. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is NZ$2,056
includes taxes & fees
1 Nov - 2 Nov
Tuscan Sky Villa in San Miniato with Private Pool
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is NZ$1,988
includes taxes & fees
26 Oct - 27 Oct
Exclusive Estate | Personal Concierge & Heated Pool
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

18. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is NZ$886
includes taxes & fees
23 Oct - 24 Oct
Villa Il Signorino
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is NZ$25,715
includes taxes & fees
27 Oct - 28 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

20. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is NZ$3,092
includes taxes & fees
28 Oct - 29 Oct
Villa Capanna: A Window onto Tuscany
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

Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi

10/10 Excellent
"This was one of the best places we stayed. We hiked the Tuscany portion of the Via Francegena and this stop was the best. The hotel is uniquely refurbished to include the 1,000 year old structures. It was an absolute delight. Blanca, was particularity helpful and accommodating. This is the best place to stay"
Douglas 1-night trip
Posted 4 hours ago
Residenza d'Epoca Palazzo Buonaccorsi

Find out more about San Gimignano

San Gimignano Villas information

Number of reviews
333
Accommodation
59 Villas
Lowest Price
NZ$259
Highest Price
NZ$25,715

Frequently asked questions

How much do villas in San Gimignano cost?
Prices for villas in San Gimignano range between NZ$259 and NZ$25,715 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 59 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.
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.