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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 $10,352
CA $11,146 total
includes taxes & fees
Oct 19 - Oct 20
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 $2,238
CA $2,589 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 $2,238
CA $2,589 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 $3,178
CA $4,356 total
includes taxes & fees
Oct 20 - Oct 21
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 $1,548
CA $1,899 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 $242
CA $271 total
includes taxes & fees
Oct 26 - Oct 27
Villa Montecastello
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

7. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (73 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $214
CA $246 total
includes taxes & fees
Oct 19 - Oct 20
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 $175
CA $208 total
includes taxes & fees
Oct 20 - Oct 21
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 $8,675
CA $8,675 total
includes taxes & fees
Oct 19 - Oct 20
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A stone building with a garden pathway leading to it.

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is CA $8,626
CA $9,421 total
includes taxes & fees
Oct 19 - Oct 20
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
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 CA $1,605
CA $2,369 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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.
The price is CA $501
CA $725 total
includes taxes & fees
Oct 19 - Oct 20
Villa Il Signorino
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

13. 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.
The price is CA $318
CA $536 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
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 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 $2,861
CA $2,899 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

15. 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 $1,054
CA $1,448 total
includes taxes & fees
Nov 1 - Nov 2
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.

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 $306
CA $373 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 covered balcony with a brick railing, a bench, and a view of lush greenery.

17. 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 $733
CA $926 total
includes taxes & fees
Oct 19 - Oct 20
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor patio with a round table and chairs, surrounded by a wooden fence and a large canopy.

18. 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 $1,531
CA $1,536 total
includes taxes & fees
Nov 2 - Nov 3
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A patio table with a patterned tablecloth, an umbrella, and metal chairs.

19. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
The price is CA $451
CA $456 total
includes taxes & fees
Oct 20 - Oct 21
Villa Falco-Cignella Resort Apartments in 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 $2,702
CA $3,005 total
includes taxes & fees
Nov 1 - Nov 2
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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"By the time you check out. You feel like you are saying goodbye to family. This hotel goes above and beyond for their guests. From Michelle, Lorenzo, Faith, etc. the whole team made out stay 5/5+. We cannot wait to go back!"
Alma 5-night trip
Posted 4 hours ago
Hotel Certosa Di Maggiano

Find out more about Siena

Siena Villas information

Number of reviews
290
Accommodation
86 Villas
Lowest Price
CA $208
Highest Price
CA $11,146

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between CA $208 and CA $11,146 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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