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

Villas in Siena

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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 landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

1. 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.
$7,870 nightly
The price is $7,870
Oct 7 - Oct 8
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Dining

2. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
Villa Liberty in The Centre - No Ztl
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

3. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,823 nightly
The price is $1,828
Nov 2 - Nov 3
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

4. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,823 nightly
The price is $1,828
Nov 2 - Nov 3
Total with taxes and fees
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.

5. 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)
$3,068 nightly
The price is $3,068
Oct 19 - Oct 20
Total with taxes and fees
Villa Mami: A Tuscan Retreat of Elegance and Charm
A stone building with a tower, surrounded by trees and a garden.

6. 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.
$1,336 nightly
The price is $1,341
Nov 2 - Nov 3
Total with taxes and fees
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

7. 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
$320 nightly
The price is $355
Oct 11 - Oct 12
Total with taxes and fees
Villa Montecastello
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

8. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (70 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$174 nightly
The price is $176
Oct 7 - Oct 8
Total with taxes and fees
Il Poggio dell'Eremita
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

9. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
$144 nightly
The price is $147
Oct 10 - Oct 11
Total with taxes and fees
Rooster House, cooking classes and opera
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

10. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
$6,125 nightly
The price is $6,125
Oct 7 - Oct 8
Total with taxes and fees
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
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.
$1,794 nightly
The price is $1,799
Nov 1 - Nov 2
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with a garden pathway leading to it.

12. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
$6,652 nightly
The price is $6,652
Oct 7 - Oct 8
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

13. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
$2,953 nightly
The price is $2,959
Nov 3 - Nov 4
Total with taxes and fees
Villa "Arnilù" with Private Pool & Wi-Fi
A two-story building with a garden, a gazebo, and a statue.

15. 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
$4,835 nightly
The price is $4,839
Oct 15 - Oct 16
Total with taxes and fees
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

16. 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.
$364 nightly
The price is $369
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa in the Florentine hills
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

17. 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.
$1,062 nightly
The price is $1,066
Oct 11 - Oct 12
Total with taxes and fees
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

18. 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
$216 nightly
The price is $264
Nov 2 - Nov 3
Total with taxes and fees
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 terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

19. 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.
$2,048 nightly
The price is $2,053
Nov 3 - Nov 4
Total with taxes and fees
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.

20. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$500 nightly
The price is $505
Oct 7 - Oct 8
Total with taxes and fees
Villa Il Signorino
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siena Hotel Reviews

Hotel Executive

Hotel Executive

10/10 Excellent
"Nice modern business hotel with spacious rooms. Mine had a balcony too. Plenty of parking on site. I ate in the restaurant which was good and reasonably priced. It’s a bit out of the way, so definitely not somewhere to explore Siena on foot by!"
Andras 1-night trip
Posted 13 hours ago
Hotel Executive

Find out more about Siena

Siena Villas information

Number of reviews
244
Accommodation
89 Villas
Lowest Price
$147
Highest Price
$7,870

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between $147 and $7,870 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 89 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.

Explore a world of travel with Expedia