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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Siena villas

Property grounds

1. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is CA $7,018
CA $7,827 total
includes taxes & fees
Aug 5 - Aug 6
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Outdoor dining

2. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,496
CA $2,853 total
includes taxes & fees
Aug 5 - Aug 6
Villa Capanna: A Window onto Tuscany
Exterior

3. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,496
CA $2,853 total
includes taxes & fees
Aug 6 - Aug 7
Villa Torre Among the Hills of Siena
Property grounds

4. 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 $1,728
CA $2,085 total
includes taxes & fees
Aug 8 - Aug 9
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 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 $257
CA $287 total
includes taxes & fees
Aug 6 - Aug 7
Villa Montecastello
Exterior

6. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is CA $1,177
CA $1,308 total
includes taxes & fees
Aug 6 - Aug 7
Villa Marcolina
Property grounds

7. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is CA $178
CA $212 total
includes taxes & fees
Aug 6 - Aug 7
Rooster House, cooking classes and opera
Exterior

8. 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 CA $582
CA $585 total
includes taxes & fees
Sep 2 - Sep 3
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Pool

9. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is CA $8,822
CA $8,822 total
includes taxes & fees
Aug 5 - Aug 6
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Pool

10. 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 $1,735
CA $2,512 total
includes taxes & fees
Sep 1 - Sep 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

11. The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is CA $217
CA $249 total
includes taxes & fees
Aug 7 - Aug 8
The three owls of san gimignano
Exterior

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 $566
CA $789 total
includes taxes & fees
Sep 2 - Sep 3
Villa Il Signorino
Property grounds

13. "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)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is CA $2,662
CA $2,701 total
includes taxes & fees
Aug 16 - Aug 17
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

14. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is CA $8,773
CA $9,581 total
includes taxes & fees
Aug 6 - Aug 7
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Exterior

15. Nice apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

Nice apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is CA $233
CA $266 total
includes taxes & fees
Aug 21 - Aug 22
Nice apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano
Outdoor dining

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (148 reviews)
"Lovely property, nicely appointed, would be happy to stay there again."
United States
David K.
The price is CA $404
CA $617 total
includes taxes & fees
Sep 2 - Sep 3
Luxury Villa in the Florentine hills
Outdoor dining

17. 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 traveller
The price is CA $2,413
CA $2,715 total
includes taxes & fees
Aug 31 - Sep 1
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

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 CA $419
CA $511 total
includes taxes & fees
Aug 27 - Aug 28
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
Exterior

19. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is CA $7,983
CA $8,582 total
includes taxes & fees
Aug 9 - Aug 10
Villa "Arnilù" with Private Pool & Wi-Fi
Pool

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

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

Siena Vip

Siena Vip

10/10 Excellent
"Fantastic location, really helpful check in service. Lovely apartment with great extras such as tea, coffee and water. Would stay there again without doubt"
Simon 2-night trip
Posted 13 hours ago
Siena Vip

Find out more about Siena

Siena Villas information

Number of reviews
171
Accommodation
90 Villas
Lowest Price
CA $212
Highest Price
CA $9,581

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between CA $212 and CA $9,581 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 90 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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