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

Villas in Siena

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$8,041 nightly
The price is $8,041
Sep 23 - Sep 24
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A brick building with a gravel courtyard, a staircase, and potted plants.

2. 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.
$327 nightly
The price is $404
Oct 5 - Oct 6
Total with taxes and fees
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.

3. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,959 nightly
The price is $1,964
Oct 17 - Oct 18
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
$1,959 nightly
The price is $1,964
Oct 17 - Oct 18
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)
$3,111 nightly
The price is $3,111
Oct 18 - Oct 19
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.
$1,434 nightly
The price is $1,439
Oct 17 - Oct 18
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
$171 nightly
The price is $191
Sep 25 - Sep 26
Total with taxes and fees
Villa Montecastello
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
$147 nightly
The price is $150
Sep 24 - Sep 25
Total with taxes and fees
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.
$2,057 nightly
The price is $2,061
Oct 4 - Oct 5
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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
$6,258 nightly
The price is $6,258
Sep 23 - Sep 24
Total with taxes and fees
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

11. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (70 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$176 nightly
The price is $179
Sep 24 - Sep 25
Total with taxes and fees
Il Poggio dell'Eremita
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.

12. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$510 nightly
The price is $515
Sep 23 - Sep 24
Total with taxes and fees
Villa Il Signorino
A stone building with a garden pathway leading to it.

13. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
$6,797 nightly
The price is $6,797
Sep 23 - Sep 24
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

14. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, 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.
$2,458 nightly
The price is $2,463
Oct 19 - Oct 20
Total with taxes and fees
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and 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
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

16. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveler
$1,270 nightly
The price is $1,274
Oct 12 - Oct 13
Total with taxes and fees
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
A table with a red and white checkered tablecloth, a hanging light fixture, and a view of green hills and trees.

17. Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Murlo
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...
United States
martina p.
$3,113 nightly
The price is $3,120
Sep 28 - Sep 29
Total with taxes and fees
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

18. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
$6,329 nightly
The price is $6,332
Oct 13 - Oct 14
Total with taxes and fees
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

19. 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.
$375 nightly
The price is $381
Oct 12 - Oct 13
Total with taxes and fees
Luxury Villa in the Florentine hills
A patio with a table and chairs, a large umbrella, and a vase of flowers.

20. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
$328 nightly
The price is $332
Sep 23 - Sep 24
Total with taxes and fees
Villa Cielo- Cignella Resort Tuscany Accommodation
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

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 8 hours ago
Hotel Chiusarelli

Find out more about Siena

Siena Villas information

Number of reviews
244
Accommodation
89 Villas
Lowest Price
$150
Highest Price
$8,041

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between $150 and $8,041 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.

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