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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 AU$264
includes taxes & fees
31 Oct - 1 Nov
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 AU$210
includes taxes & fees
3 Nov - 4 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 AU$1,840
includes taxes & fees
2 Nov - 3 Nov
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 AU$2,418
includes taxes & fees
2 Nov - 3 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 AU$300
includes taxes & fees
4 Nov - 5 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 AU$2,253
includes taxes & fees
29 Nov - 30 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 AU$2,568
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 AU$2,864
includes taxes & fees
9 Nov - 10 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 AU$8,555
includes taxes & fees
2 Nov - 3 Nov
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
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A courtyard with a building, potted plants, and a grassy area.

11. 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 AU$3,406
includes taxes & fees
2 Nov - 3 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

12. 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 AU$11,103
includes taxes & fees
30 Oct - 31 Oct
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

13. 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 AU$516
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A stone building with a swimming pool, wooden deck, and a tall tree.

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
The price is AU$1,706
includes taxes & fees
3 Nov - 4 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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 AU$933
includes taxes & fees
1 Nov - 2 Nov
Aureva Tuscany, modern villa with private pool
A stone building with a large arched entrance, potted plants, and outdoor seating.

16. 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 AU$1,502
includes taxes & fees
1 Nov - 2 Nov
Exclusive Estate | Personal Concierge & Heated Pool
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

17. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is AU$4,146
includes taxes & fees
9 Nov - 10 Nov
Villa Mami: A Tuscan retreat full of elegance and charm
A table set for tea with a view of a garden and hills.

18. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is AU$1,646
includes taxes & fees
11 Nov - 12 Nov
Tuscan Sky Villa in San Miniato with Private 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.

19. 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 AU$700
includes taxes & fees
30 Oct - 31 Oct
Villa Il Signorino
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AU$20,623
includes taxes & fees
30 Oct - 31 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
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

Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery

10/10 Excellent
"A beautiful, peaceful hotel."
Aileen 2-night trip
Posted 8 hours ago
Tenuta Sovestro - Agriturismo e Winery

Find out more about San Gimignano

San Gimignano Villas information

Number of reviews
334
Accommodation
59 Villas
Lowest Price
AU$210
Highest Price
AU$20,623

Frequently asked questions

How much do villas in San Gimignano cost?
Villas in San Gimignano cost between AU$210 and AU$20,623 per night. These stays give you the privacy of your own space at a price you can afford. This price was 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?
There are 59 villas in San Gimignano. Whether you're holidaying with the family or planning a weekend escape with some friends, Expedia will help you find the ideal base for your crew.
What is there to do near my villa in San Gimignano?
There are plenty of fun things to fill your itinerary with in San Gimignano. You won't want to miss renowned attractions like Tenuta Torciano Winery, Sovestro in Poggio Winery and Castello di Monsanto. Castello della Paneretta, Museo Civico and Castle of Oliveto also appeal to many visitors.