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

1. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

$8,447 nightly

Nov 12 - Nov 13

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.

2. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,654 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

3. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,654 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Toscana

$2,823 nightly

Nov 21 - Nov 22

Total with taxes and fees

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

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

Vico dʼArbia

Marina O.

$1,219 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

6. Villa Montecastello

Monteriggioni

Alvaro

$319 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

7. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$163 nightly

Nov 20 - Nov 21

Total with taxes and fees

A large estate with a swimming pool, tennis court, and multiple guest rooms.

8. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

$13,149 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

$131 nightly

Nov 11 - Nov 12

Total with taxes and fees

A stone building with a garden pathway leading to it.

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

$7,132 nightly

Nov 13 - Nov 14

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

"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...

JIm B.

$1,197 nightly

Nov 15 - Nov 16

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.

$1,727 nightly

Nov 15 - Nov 16

Total with taxes and fees

A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

13. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Rapolano Terme

Toon M.

$1,011 nightly

Nov 16 - Nov 17

Total with taxes and fees

A courtyard with a pathway, a small pool, and a variety of trees and shrubs.

14. 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

$215 nightly

Nov 13 - Nov 14

Total with taxes and fees

A covered balcony with a brick railing, a bench, and a view of lush greenery.

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

$1,295 nightly

Nov 11 - Nov 12

Total with taxes and fees

A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

16. Red Heart - Relax with Your Loved Ones in Tuscany

Trequanda

$869 nightly

Nov 13 - Nov 14

Total with taxes and fees

A villa with a swimming pool, surrounded by lush greenery and vineyards.

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

Montespertoli

$6,017 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

18. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Vaggio

$1,152 nightly

Nov 15 - Nov 16

Total with taxes and fees

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

19. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Torrita di Siena

"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."

Nate D.

$2,261 nightly

Nov 16 - Nov 17

Total with taxes and fees

A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

$15,779 nightly

Nov 11 - Nov 12

Total with taxes and fees

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Top Siena Hotel Reviews

Palazzo Ravizza

8/10 Good

"Convenient place to stay with car to tour Tuscany. Breakfast was good. Room cleaned daily. Charming old building. Hotel works closely with you to navigate the ZTL; you need to be able to walk up some stairs from car park down the hill after dropping your bags at the main door. Away from the bustle around the piazzas: quiet. You need to not mind walking up and down hills to enjoy Siena and most of the historic towns in Tuscany. Staff at front desk fluent in English."

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Charming, beautifully decorated, and pet-friendly hotel We enjoyed our stay at this charming hotel. It is very cutely decorated and has lots of character. The location is great if you prefer staying outside the busy city center while still having convenient access to everything. The room was a good size—not too big or too small—with a comfortable bed and a spacious bathroom. Breakfast was also very good, offering everything you need to start the day. Another big plus is that the hotel is pet-friendly! If I had to mention anything, it would be a few minor finishing details, such as the AC vents, that seemed a little unfinished. Nothing major, just small touches that could make the overall experience even better. Overall, a lovely hotel with charm, comfortable rooms, and a welcoming atmosphere. We would happily stay again!"

Find out more about Siena

Siena Villas information

Number of reviews	97
Accommodation	89 Villas
Lowest Price	$135
Highest Price	$15,779

Frequently asked questions

How much do villas in Siena cost?

You can expect to pay between $135 and $15,779 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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Room 1

Check prices for these dates

Our top choices for Siena villas

1. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

2. Villa Capanna: A Window onto Tuscany

3. Villa Torre Among the Hills of Siena

4. Villa Mami: A Tuscan retreat full of elegance and charm

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

6. Villa Montecastello

7. Il Poggio dell'Eremita

8. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

9. Rooster House, Cooking Classes, and Opera

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

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 Fornacino" with Pool, Garden & Wi-Fi

14. 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

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

16. Red Heart - Relax with Your Loved Ones in Tuscany

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

18. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

19. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Find vacation rentals that suit your style

Top Siena Hotel Reviews

Palazzo Ravizza

Hotel Athena

Il Chiostro del Carmine

Hotel Italia

Best Western Hotel San Marco

Villa Ermellina Siena, a Tribute Portfolio Hotel

Relais degli Angeli

ApartHotel Anghel

Borgo Grondaie

Find out more about Siena

Siena Villas information

Frequently asked questions

Explore a world of travel with Expedia

Villas in Siena

Check prices for these dates

Our top choices for Siena villas

1. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

2. Villa Capanna: A Window onto Tuscany

3. Villa Torre Among the Hills of Siena

4. Villa Mami: A Tuscan retreat full of elegance and charm

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

6. Villa Montecastello

7. Il Poggio dell'Eremita

8. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

9. Rooster House, Cooking Classes, and Opera

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

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 Fornacino" with Pool, Garden & Wi-Fi

14. 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

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

16. Red Heart - Relax with Your Loved Ones in Tuscany

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

18. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

19. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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