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

1. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

$8,093 nightly

Sep 17 - Sep 18

Total with taxes and fees

2. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,972 nightly

Oct 17 - Oct 18

Total with taxes and fees

3. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,972 nightly

Oct 17 - Oct 18

Total with taxes and fees

4. Stunning villa with large pool in the heart of Chianti 12km from Siena

Radda in Chianti

ana r.

$936 nightly

Sep 27 - Sep 28

Total with taxes and fees

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

Vico dʼArbia

Marina O.

$1,444 nightly

Oct 17 - Oct 18

Total with taxes and fees

Villa, Air conditioning, Courtyard View | Exterior

6. Villa Montecastello

Monteriggioni

Alvaro

$172 nightly

Sep 26 - Sep 27

Total with taxes and fees

7. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

$148 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

$6,299 nightly

Sep 17 - Sep 18

Total with taxes and fees

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

Radda in Chianti

Amber M.

$1,108 nightly

Sep 23 - Sep 24

Total with taxes and fees

10. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$179 nightly

Sep 24 - Sep 25

Total with taxes and fees

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

$6,841 nightly

Sep 21 - Sep 22

Total with taxes and fees

12. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$515 nightly

Sep 17 - Sep 18

Total with taxes and fees

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

Gaiole in Chianti

Bernard K.

$2,768 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

Certaldo

$6,370 nightly

Oct 17 - Oct 18

Total with taxes and fees

15. 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.

$2,245 nightly

Sep 29 - Sep 30

Total with taxes and fees

16. Luxury Villa in the Florentine hills

Florence

melissa r.

$378 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

$1,278 nightly

Oct 12 - Oct 13

Total with taxes and fees

18. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Montespertoli

$6,924 nightly

Oct 15 - Oct 16

Total with taxes and fees

19. Villa Bellavista - Homelike Villas

Montegonzi

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

Tavarnelle Val di Pesa

$964 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Siena Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Great place for a short stay! Beautiful garden breakfast. The only minor compliant was the elevator. There is only one and it was very slow."

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"Sara at the front desk was so helpful. She spoke very good English and even helped me a little with enunciating some things in Italian. She helped us with where to find parking (free) in Siena, and also helped us with some different wine tours and tastings. She was always there with a smile and a helpful information. The villa itself was beautiful, with lovely grounds and a well kept pool! We will definitely come back."

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

Find out more about Siena

Siena Villas information

Number of reviews	239
Accommodation	89 Villas
Lowest Price	$151
Highest Price	$8,093

Frequently asked questions

How much do villas in Siena cost?

You can expect to pay between $151 and $8,093 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

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Upfront pricing

Check prices for these dates

Our top choices for Siena villas

1. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

2. Villa Capanna: A Window onto Tuscany

3. Villa Torre Among the Hills of Siena

4. Stunning villa with large pool in the heart of Chianti 12km from Siena

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

6. Villa Montecastello

7. Rooster House, cooking classes and opera

8. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

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

10. Il Poggio dell'Eremita

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

12. Villa Il Signorino

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

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

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

16. Luxury Villa in the Florentine hills

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

18. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

19. Villa Bellavista - Homelike Villas

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

Find vacation rentals that suit your style

Top Siena Hotel Reviews

Palazzo Ravizza

Find out more about Siena

Siena Villas information

Frequently asked questions

Explore a world of travel with Expedia