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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Siena

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Relax in a serene outdoor space with a lush landscape view, a pool, and comfortable seating.

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We had a large group of family and friends comfortably stay here. The host was very available and helpful, and personally showed us around the property upon our arrival. The property description is accurate. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Relax in a serene outdoor space surrounded by lush greenery and a tranquil body of water.

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (102)
"Beautiful home, beautiful views. "
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Relax in style on the patio, surrounded by lush views and a refreshing pool.

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (10)
"We were two couples looking for an authentic Tuscan experience in the gorgeous countryside. The location is well suited to travel to Montalpucino, Chianti, San Gimignano, Volterra, Pisa and Florence. Both Mido and David were very attentive towards making our visit comfortable . A gorgeous building with high quality style and finishes. A top contender for best vrbo property I have ever visited. Thank you!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Private villa in the heart of chianti with view of siena
Relax by the serene pool surrounded by lounge chairs and tables under a large tree.

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (1)
"Fantastiskt boende med underbar trädgård och utsikt, nära vingårdar och historiska städer!"
Private villa in the heart of chianti with view of siena
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Relax by the pool with comfortable lounge chairs and a wicker basket for your essentials.

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Villa with unique view of Siena with private pool
Stroll through the beautifully maintained garden, featuring a variety of flowering plants and a charming, rustic building with an arched doorway.

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Guests can relax on the outdoor bench amidst a serene garden with flowering plants and a tree.

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (35)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
XIII Century Tower with Private Panoramic Pool
Exterior

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool
Villa Larniano, With Private Pool And View On Vineyard
Enjoy al fresco dining with a view of the lush landscape from this outdoor dining area.

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
Villa luna with pool and garden near the center of Siena
Stroll through the serene courtyard surrounded by lush potted plants and a charming building with an arched entrance and balcony.

Villa luna with pool and garden near the center of Siena

9.0 out of 10, Wonderful, (27)
"We had a great time "
Villa luna with pool and garden near the center of Siena
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Relax by the serene pool surrounded by lush greenery and comfortable lounge seating.

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Relax by the serene pool surrounded by lush greenery and breathtaking countryside views.

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (90)
"We felt so at home and at peace here. Everything was perfect and location is ideal for day trips around Tuscany. Highly recommend!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Stroll through the serene garden, featuring a tranquil pool and beautifully manicured hedges.

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Villa in Siena with 4 bedrooms sleeps 8
Relax in a hot tub surrounded by lush gardens and a brick wall enclosure.

Villa in Siena with 4 bedrooms sleeps 8

10.0 out of 10, Exceptional, (42)
"Beautiful location! Owners very friendly and helpful. Would suggest this place for anyone visiting Sienna."
Villa in Siena with 4 bedrooms sleeps 8
VILLA SIENA is 4 km from Siena 10PAX AC, POOL & SPA total privacy.
Enjoy a romantic meal under the pergola, surrounded by lush greenery and beautifully set tables.

VILLA SIENA is 4 km from Siena 10PAX AC, POOL & SPA total privacy.

9.6 out of 10, Exceptional, (14)
"Well equiped comfortable villa, conveniently close to the city that offers spectacular views of Tuscany. Perfect for friends and family. The location is ideally suited to explore the surrounding villages and cities. The villa is furnished with all the conveniences expected from a country home and more! We really enjoyed our stay and could not fault any of the home's features. Thanks to our host Marco."
VILLA SIENA is 4 km from Siena 10PAX AC, POOL & SPA total privacy.
Il Boschetto an oasis of peace and nature in Siena
Enjoy a serene swim in our pool surrounded by lush greenery and a natural landscape.

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (34)
"The rooms are spacious and well equipped and the house can easily accommodate 10 people. The property is located in a wealthy enclave of Siena minutes from town yet it is completely private. The views are breathtaking and the property is gorgeous."
Il Boschetto an oasis of peace and nature in Siena
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Enjoy a serene view of rolling hills and a distant village from this room's balcony.

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

9.8 out of 10, Exceptional, (44)
"Our stay in Sara's house was wonderful! She's was very helpful and responsive during our visit. She had to wait over an hour for us to arrive because we got lost and was so patient and kind! The house is lovely! It's spacious and comfortable and over looks the stunning Tuscan hillside. The views take your breath away! The outside patio area is beautifully landscaped with several seating areas to relax and take in the beauty. We had our breakfast outside every morning. The outside seating area is...
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Stunning Villa, With Private Pool At 6km From Siena
Stately building with a traditional facade, adorned with climbing ivy and surrounded by lush greenery.

Stunning Villa, With Private Pool At 6km From Siena

10.0 out of 10, Exceptional, (61)
"This villa was perfect for three families! It had everything we needed and the pool was refreshing and lovely. The hosts were amazing and very helpful! Thank you!"
Stunning Villa, With Private Pool At 6km From Siena
Porta Romana Elegant House with Private Parking!
Interior

Porta Romana Elegant House with Private Parking!

8.8 out of 10, Excellent, (3)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
Porta Romana Elegant House with Private Parking!
Detached villa with swimming pool and pizza oven for groups up to fourteen people.
Enjoy a romantic meal under the shade of a large umbrella, surrounded by a scenic view of rolling hills and lush greenery.

Detached villa with swimming pool and pizza oven for groups up to fourteen people.

9.2 out of 10, Wonderful, (15)
"little things, no personal contact with the landlord/manager"
Detached villa with swimming pool and pizza oven for groups up to fourteen people.
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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Frequently asked questions

How much do villas in Siena cost?
Villas in Siena cost between and per night. These getaways provide the privacy to enjoy your own space at a price that won't stretch the budget. This price was 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?
Pack your suitcase and pick from 78 villas in Siena. For a family escape, a romantic break or anything in between, Expedia will help you find the perfect place in just a few clicks.
What is there to do near my villa in Siena?
No matter your interests, Siena has lots of things to keep you entertained. Siena Cathedral, Monteriggioni Castle and Palazzo Pubblico are on many visitors' sightseeing itineraries. Don't forget to explore Civic Museum, Museo dellOpera del Duomo and Terra di Seta either. With Expedia's hotel deals in Siena, you can see more popular attractions like these with the cash you save.