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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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 HK$1,341
HK$2,717 total
includes taxes & fees
7 Sept - 8 Sept
GuestHost - Porta Romana Elegant House with Private Parking!
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

2. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is HK$39,441
HK$43,982 total
includes taxes & fees
31 Aug - 1 Sept
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
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
The price is HK$15,586
HK$17,593 total
includes taxes & fees
14 Sept - 15 Sept
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
The price is HK$14,027
HK$16,035 total
includes taxes & fees
5 Sept - 6 Sept
Villa Torre Among the Hills of Siena

5. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is HK$6,131
HK$12,021 total
includes taxes & fees
1 Sept - 2 Sept
The San Leonino House
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.
The price is HK$9,711
HK$11,719 total
includes taxes & fees
6 Sept - 7 Sept
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
The price is HK$1,504
HK$1,682 total
includes taxes & fees
3 Sept - 4 Sept
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
Toscana
The price is HK$999
HK$1,190 total
includes taxes & fees
1 Sept - 2 Sept
Rooster House, cooking classes and opera
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

9. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (69 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is HK$1,225
HK$1,415 total
includes taxes & fees
6 Sept - 7 Sept
Il Poggio dell'Eremita
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

10. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"We loved this villa! David, our host, was very prompt in responding and providing additional information. The property was beautiful. We will definitely stay here again."
United States
John G.
The price is HK$1,453
HK$2,634 total
includes taxes & fees
31 Aug - 1 Sept
Luxury Villa in the Florentine hills
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 HK$4,386
HK$8,754 total
includes taxes & fees
17 Sept - 18 Sept
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.

12. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is HK$49,577
HK$49,577 total
includes taxes & fees
31 Aug - 1 Sept
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A rustic stone building with a patio, outdoor seating, and a garden with various plants and flowers.

13. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is HK$3,406
HK$3,424 total
includes taxes & fees
30 Sept - 1 Oct
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
A stone building with a garden pathway leading to it.

14. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Montalcino
The price is HK$49,301
HK$53,842 total
includes taxes & fees
31 Aug - 1 Sept
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
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.

15. 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 HK$2,861
HK$4,133 total
includes taxes & fees
2 Sept - 3 Sept
Villa Il Signorino

16. 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 HK$34,289
HK$34,316 total
includes taxes & fees
30 Sept - 1 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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.
The price is HK$18,120
HK$19,537 total
includes taxes & fees
29 Sept - 30 Sept
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
An aerial view of a property with a large central building, a courtyard with a circular garden, and surrounding structures.

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
The price is HK$2,377
HK$2,900 total
includes taxes & fees
22 Sept - 23 Sept
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 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.
The price is HK$17,302
HK$17,520 total
includes taxes & fees
18 Sept - 19 Sept
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

20. 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 HK$10,634
HK$12,885 total
includes taxes & fees
6 Sept - 7 Sept
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
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

10/10 Excellent
"The staff was very candid and friendly, the breakfast was very good"
Joe 4-night trip
Posted 2 hours ago
Hotel Chiusarelli

Find out more about Siena

Siena Villas information

Number of reviews
245
Accommodation
85 Villas
Lowest Price
HK$1,190
Highest Price
HK$53,842

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between HK$1,190 and HK$53,842 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 85 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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