Siena Villas from CA $175

A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

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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!

Siena

Kathleen M.

CA $552 total

includes taxes & fees

Sep 14 - Sep 15

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

Siena

CA $7,775 total

includes taxes & fees

Sep 10 - Sep 11

3. Villa Liberty in The Centre - No Ztl

Siena Historical Center

CA $951 total

includes taxes & fees

Oct 6 - Oct 7

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

4. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

CA $2,837 total

includes taxes & fees

Sep 14 - Sep 15

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

5. Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $2,835 total

includes taxes & fees

Sep 15 - Sep 16

An outdoor seating area with two sofas and a table, a stone wall, and a view of greenery.

6. The San Leonino House

Castellina in Chianti

CA $2,125 total

includes taxes & fees

Sep 10 - Sep 11

A stone building with a tower, surrounded by trees and a garden.

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia

Marina O.

CA $2,073 total

includes taxes & fees

Sep 11 - Sep 12

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. Villa Montecastello

Monteriggioni

Alvaro

CA $255 total

includes taxes & fees

Sep 26 - Sep 27

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

9. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

CA $210 total

includes taxes & fees

Sep 10 - Sep 11

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

10. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

CA $8,764 total

includes taxes & fees

Sep 10 - Sep 11

A stone building with a swimming pool, wooden deck, and a tall tree.

11. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

Amber M.

CA $1,548 total

includes taxes & fees

Sep 17 - Sep 18

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

12. Il Poggio dell'Eremita

Sinalunga

Paul Q.

CA $249 total

includes taxes & fees

Sep 15 - Sep 16

A stone building with a garden pathway leading to it.

13. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

CA $9,518 total

includes taxes & fees

Sep 10 - Sep 11

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.

14. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $726 total

includes taxes & fees

Sep 9 - Sep 10

A building with a yellow exterior, a door with a number 11 sign, and a window with a potted plant.

15. The three owls of san gimignano

San Gimignano

CA $175 total

includes taxes & fees

Sep 18 - Sep 19

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

16. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

CA $3,819 total

includes taxes & fees

Sep 10 - Sep 11

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

Murlo

"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...

martina p.

CA $3,133 total

includes taxes & fees

Sep 29 - Sep 30

An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

18. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"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!"

Anonymous traveller

CA $1,840 total

includes taxes & fees

Sep 10 - Sep 11

An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

19. Luxury Villa in the Florentine hills

Florence

melissa r.

CA $626 total

includes taxes & fees

Sep 28 - Sep 29

A stone building with a tiled roof, surrounded by trees and potted plants.

20. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Tavarnelle Val di Pesa

CA $1,347 total

includes taxes & fees

Oct 4 - Oct 5

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Top Siena Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"All the staff in the hotel were very helpful and we would like to stay there again."

Hotel Santa Caterina

10/10 Excellent

"Great location just outside the limited traffic zone, and available parking. Staff were very accommodating and friendly. Fantastic breakfast spread with a lovely view of the Tuscan hills. The room was on the smaller side, but more than adequate for one person for a short stay. The a/c worked very well!"

Hotel Minerva

10/10 Excellent

"We would first like to thank Alessandra at the front desk she was so friendly, knowledgeable, informative, friendly, she helped us soo much! The hotel is great, clean, rooms decent size , bathroom is average size , the room and bathroom clean, and the staff was so great and friendly. Great location close to everything, and well maintained. They offered underground parking $20 night, no outside parking. The breakfast was great and the staff so friendly. Great outside area for sitting and breakfast.we had a balcony with amazing views."

Find out more about Siena

Siena Villas information

Number of reviews	242
Accommodation	90 Villas
Lowest Price	CA $175
Highest Price	CA $9,518

Frequently asked questions

How much do villas in Siena cost?

You can expect to pay between CA $175 and CA $9,518 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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Search Siena Villa Rentals from CA $175

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena villas

1. GuestHost - Porta Romana Elegant House with Private Parking!

2. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

3. Villa Liberty in The Centre - No Ztl

4. Villa Capanna: A Window onto Tuscany

5. Villa Torre Among the Hills of Siena

6. The San Leonino House

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

8. Villa Montecastello

9. Rooster House, cooking classes and opera

10. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

11. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

12. Il Poggio dell'Eremita

13. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

14. Villa Il Signorino

15. The three owls of san gimignano

16. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

17. Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

18. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

19. Luxury Villa in the Florentine hills

20. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Find vacation rentals that suit your style

Top Siena Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Siena

Siena Villas information

Frequently asked questions

Explore a world of travel with Expedia