A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Siena villas

A brick building with a gravel courtyard, a staircase, and potted plants.

1. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is CA $197
CA $430 total
includes taxes & fees
Oct 11 - Oct 12
GuestHost - Porta Romana Elegant House with Private Parking!
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

2. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,144
CA $2,497 total
includes taxes & fees
Oct 17 - Oct 18
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

3. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,144
CA $2,497 total
includes taxes & fees
Oct 17 - Oct 18
Villa Torre Among the Hills of Siena
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

4. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,190
CA $4,372 total
includes taxes & fees
Oct 23 - Oct 24
Villa Mami: A Tuscan Retreat of Elegance and Charm
A stone building with a tower, surrounded by trees and a garden.

5. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is CA $1,554
CA $1,906 total
includes taxes & fees
Nov 5 - Nov 6
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

6. 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 $251
CA $281 total
includes taxes & fees
Oct 12 - Oct 13
Villa Montecastello
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

7. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (72 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $215
CA $249 total
includes taxes & fees
Oct 13 - Oct 14
Il Poggio dell'Eremita
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

8. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is CA $175
CA $209 total
includes taxes & fees
Oct 12 - Oct 13
Rooster House, cooking classes and opera
A stone building with a swimming pool, wooden deck, and a tall tree.

9. 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 $1,790
CA $2,557 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

10. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is CA $2,874
CA $2,913 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
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.

11. 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 CA $502
CA $721 total
includes taxes & fees
Oct 20 - Oct 21
Villa Il Signorino
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, (151 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 $319
CA $533 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
A large building surrounded by dense trees and a clear sky.

13. 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 $6,881
CA $6,886 total
includes taxes & fees
Oct 15 - Oct 16
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

14. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is CA $1,120
CA $1,516 total
includes taxes & fees
Oct 13 - Oct 14
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

15. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

16. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Trequanda
The price is CA $308
CA $375 total
includes taxes & fees
Nov 2 - Nov 3
Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
A covered balcony with a brick railing, a bench, and a view of lush greenery.

17. 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 $735
CA $930 total
includes taxes & fees
Oct 15 - Oct 16
Villa in the Heart of Chianti — Peace, Views, and Authentic 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 Siena Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

8/10 Good
"Very helpful staff with easy access to Siena by local buses. Good variety of breakfast items. Quiet location."
Mark 2-night trip
Posted 2 hours ago
Villa Scacciapensieri Boutique Hotel

Find out more about Siena

Siena Villas information

Number of reviews
250
Accommodation
86 Villas
Lowest Price
CA $209
Highest Price
CA $6,886

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between CA $209 and CA $6,886 per night for villas in Siena. Whatever your budget, the perfect getaway is only clicks away 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 Siena?
Siena has 86 villas to select from. Find your ideal stay quickly and easily by checking the "Villa" box under the "Property type" tab in our filter tool.
Why book your villa in Siena with Expedia?
Booking a villa in Siena is as simple as working out your travel dates and selecting an option that meets your needs. Searching for something luxurious or low cost, or a property that also comes with free WiFi? Use Expedia's search filters to narrow your results and find the ideal fit.
How can I find cheap villas in Siena?
Expedia is here to help you easily source cheap villas in Siena. Use our convenient filter tool to select amenities, budget and star rating to refine your search and find the best place to stay in a matter of clicks.
What is there to do near my villa in Siena?
You'll find loads of terrific things to fill your days in Siena. Drop by big attractions like Museo dell'Acqua, Accademia Musicale Chigiana and Basilica dell'Osservanza. Palasport Mens Sana, Porta Romana and San Spirito are also visited by many.

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