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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 - 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 $10,184
CA $10,966 total
includes taxes & fees
Oct 29 - Oct 30
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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 $1,981
CA $2,327 total
includes taxes & fees
Nov 2 - Nov 3
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 $1,981
CA $2,327 total
includes taxes & fees
Nov 2 - Nov 3
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 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 $3,127
CA $4,286 total
includes taxes & fees
Nov 3 - Nov 4
Villa Mami: A Tuscan retreat full 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 $1,371
CA $1,716 total
includes taxes & fees
Nov 2 - Nov 3
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 $233
CA $261 total
includes taxes & fees
Oct 29 - Oct 30
Villa Montecastello
A stone building with two arched entrances, surrounded by a well-maintained garden with various flowers and plants.

7. 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 $217
CA $248 total
includes taxes & fees
Oct 29 - Oct 30
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 $172
CA $205 total
includes taxes & fees
Oct 30 - Oct 31
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.

9. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is CA $8,534
CA $8,534 total
includes taxes & fees
Oct 29 - Oct 30
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A stone building with a swimming pool, wooden deck, and a tall tree.

10. 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 $934
CA $1,685 total
includes taxes & fees
Nov 2 - Nov 3
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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 $8,487
CA $9,268 total
includes taxes & fees
Oct 29 - Oct 30
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

12. 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 $1,037
CA $1,425 total
includes taxes & fees
Nov 1 - Nov 2
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

13. 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 $2,392
CA $2,430 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

14. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 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 $313
CA $519 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
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 CA $493
CA $704 total
includes taxes & fees
Oct 29 - Oct 30
Villa Il Signorino
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 $301
CA $367 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 swimming pool with stone tiles, surrounded by trees and a view of the countryside.

17. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Torrita di Siena
10.0 out of 10, Exceptional, (1 review)
"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."
United States
Nate D.
The price is CA $3,172
CA $3,175 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

18. 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 $1,627
CA $1,817 total
includes taxes & fees
Nov 2 - Nov 3
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
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 $1,616
CA $1,621 total
includes taxes & fees
Nov 2 - Nov 3
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 $2,658
CA $3,036 total
includes taxes & fees
Nov 2 - Nov 3
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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Top Siena Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Classic room with beautiful view. Accommodating staff."
Hui 1-night trip
Posted less than an hour ago
Palazzo Ravizza

Find out more about Siena

Siena Villas information

Number of reviews
294
Accommodation
86 Villas
Lowest Price
CA $205
Highest Price
CA $10,966

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between CA $205 and CA $10,966 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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