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Nov 20 - Nov 22
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Our top choices for Siena villas

A dining area with a wooden table, white chairs, and a chandelier.

1. 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 long wooden table set for a meal with a view of a hillside town.

2. 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 CA $11,137
CA $11,923 total
includes taxes & fees
Nov 16 - Nov 17
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A stone building with a tiled roof, surrounded by a well-maintained lawn and trees.

3. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $1,993
CA $2,341 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $1,993
CA $2,341 total
includes taxes & fees
Nov 16 - Nov 17
Villa Torre Among the Hills of Siena
A large estate with multiple buildings, a swimming pool, and surrounding olive groves.

5. 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 CA $3,146
CA $4,087 total
includes taxes & fees
Nov 18 - Nov 19
Villa Mami: A Tuscan retreat full of elegance and charm
A narrow road leading to a stone building with arched doorways, surrounded by olive trees and greenery.

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 CA $1,379
CA $1,726 total
includes taxes & fees
Nov 16 - Nov 17
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
An outdoor dining area with a table set for two, a large umbrella, and a view of a historic building in the background.

7. VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8

VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8
Montalcino
The price is CA $5,810
CA $5,810 total
includes taxes & fees
Nov 16 - Nov 17
VILLA IL POGGIO - Four Bedroom Villa, Sleeps 8
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. 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 $500
CA $555 total
includes taxes & fees
Nov 22 - Nov 23
Villa Montecastello
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, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $243
CA $266 total
includes taxes & fees
Nov 17 - Nov 18
Il Poggio dell'Eremita
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

10. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is CA $173
CA $184 total
includes taxes & fees
Nov 17 - Nov 18
Rooster House, Cooking Classes, and Opera
A stone building with a garden pathway leading to it.

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is CA $9,281
CA $10,067 total
includes taxes & fees
Nov 16 - Nov 17
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
A large estate with a swimming pool, tennis court, and multiple guest rooms.

12. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is CA $18,561
CA $18,561 total
includes taxes & fees
Nov 29 - Nov 30
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A stone building with a swimming pool, wooden deck, and a tall tree.

13. 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 CA $939
CA $1,943 total
includes taxes & fees
Nov 18 - Nov 19
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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 $1,044
CA $1,433 total
includes taxes & fees
Nov 16 - Nov 17
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
A courtyard with a pathway, a small pool, and a variety of trees and shrubs.

15. 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 $303
CA $370 total
includes taxes & fees
Nov 22 - Nov 23
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
An outdoor patio with a stone wall, a wooden bench, a cushioned sofa, and umbrellas providing shade.

16. 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 $2,407
CA $2,444 total
includes taxes & fees
Nov 16 - Nov 17
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $22,273
CA $22,273 total
includes taxes & fees
Nov 16 - Nov 17
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A villa with a swimming pool, surrounded by lush greenery and vineyards.

18. 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 CA $8,494
CA $8,500 total
includes taxes & fees
Nov 16 - Nov 17
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

19. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
The price is CA $1,869
CA $1,873 total
includes taxes & fees
Nov 16 - Nov 17
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

20. 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 CA $2,045
CA $2,218 total
includes taxes & fees
Nov 29 - Nov 30
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
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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Learn more about Siena

Medieval brick buildings circle the shell-shaped Piazza del Campo where the thrilling Palio horse race happens twice each summer. Climb the Torre del Mangia for sweeping views, then explore the zebra-striped Duomo where even the marble floor tells fascinating stories.

See all hotels in Siena
A historic cathedral with a rainbow, surrounded by traditional buildings.

Frequently Asked Questions

How much do villas in Siena cost?

You can expect to pay between CA $173 and CA $22,273 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 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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