Siena Villas Rentals

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.

$289 nightly

Oct 5 - Oct 6

Total with taxes and fees

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

2. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

Ron M.

$7,989 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

3. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,947 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

4. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,947 nightly

Oct 17 - Oct 18

Total with taxes and fees

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

5. Villa Mami: A Tuscan Retreat of Elegance and Charm

Toscana

$2,924 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

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

Vico dʼArbia

Marina O.

$1,425 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

7. Villa Montecastello

Monteriggioni

Alvaro

$158 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

8. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

$146 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

9. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$174 nightly

Oct 7 - Oct 8

Total with taxes and fees

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

$6,218 nightly

Sep 28 - Sep 29

Total with taxes and fees

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.

$2,043 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

12. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

$1,663 nightly

Oct 6 - Oct 7

Total with taxes and fees

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.

13. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$478 nightly

Sep 28 - Sep 29

Total with taxes and fees

A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

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

Certaldo

$6,288 nightly

Oct 12 - Oct 13

Total with taxes and fees

An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

15. Villa Bellavista - Homelike Villas

Montegonzi

A table with a red and white checkered tablecloth, a hanging light fixture, and a view of green hills and trees.

16. 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.

$3,093 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

17. 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 traveler

$1,301 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

18. Luxury Villa in the Florentine hills

Florence

melissa r.

$388 nightly

Sep 28 - Sep 29

Total with taxes and fees

A stone building with a garden pathway leading to it.

19. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

$6,752 nightly

Sep 28 - Sep 29

Total with taxes and fees

A stone building with a large glass door, a wooden deck, and a stone wall.

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

San Gimignano

$6,043 nightly

Sep 28 - Sep 29

Total with taxes and fees

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Top Siena Hotel Reviews

Four Points by Sheraton Siena

10/10 Excellent

"Excellent property. It was well maintained, and the staff was friendly. I would definitely stay here again."

Piccolo Hotel Etruria

8/10 Good

"While we were thankful for the private washroom it was really small. Shower was small but we managed to get clean. This property is a great location. Tons of restaurants and shopping. The square was fabulous. We ate dinner in a castle but the highlight was the valet parking. The garage you park at is about 15 minute drive to hotel. They drive you, help you with your luggage, pick you up at the end of your stay and drive you back to their garage. The ride to and from is INSANE. Twists and turns and hills, and tight turns not to mention 100’s of people walking around those same streets. I have driven in every major city in Canada and the US. This was unique. Very thankful for our drivers. We would definitely stay here again and we wished we had booked a longer stay."

Relais La Corte Dei Cavalieri

8/10 Good

"Staff was exceedingly helpful and accommodating. Self check in and Check Out were easy. Staff communicated well, but if you prefer to be left alone, you don't have to interact with anyone at all. Very good for an awkward, anxious North American traveller. Main property, rooms, and hallway were well maintained. I really liked the decor and space provided. However, patio was overgrown, dirty, and unusable except if you need to smoke. Bedding and bathroom were clean; but bed had a corner that sunk and one of the towels had an odd rust stain on it perhaps from the towel rail? I would stay there again if they'd have me. Great value for a last minute nip into Siena for a week."

Find out more about Siena

Siena Villas information

Number of reviews	245
Accommodation	89 Villas
Lowest Price	$149
Highest Price	$7,989

Frequently asked questions

How much do villas in Siena cost?

You can expect to pay between $149 and $7,989 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 89 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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Things to do in Siena

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Villas in Siena

Bundle & Save

OneKeyCash

Upfront pricing

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 32

3. Villa Capanna: A Window onto Tuscany

4. Villa Torre Among the Hills of Siena

5. Villa Mami: A Tuscan Retreat of Elegance and Charm

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

7. Villa Montecastello

8. Rooster House, cooking classes and opera

9. Il Poggio dell'Eremita

10. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

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

12. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

13. Villa Il Signorino

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

15. Villa Bellavista - Homelike Villas

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

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

18. Luxury Villa in the Florentine hills

19. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

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

Find vacation rentals that suit your style

Top Siena Hotel Reviews

Four Points by Sheraton Siena

Find out more about Siena

Siena Villas information

Frequently asked questions

Explore a world of travel with Expedia