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Featured Villas in Siena and around

Our top choices for Siena villas

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We loved our stay, it was beautiful and relaxing beyond words! Francesca and her team were amazing, providing so many memorable experiences and great support! We will be back! What a wonderful time all around. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

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

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

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."
The price is €1,282
includes taxes & fees
8 Sept - 9 Sept
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"Our stay was absolutely delightful. The house is perched atop a hill, offering sweeping views of the surrounding vineyards—pure Tuscan magic. There’s plenty of outdoor seating to soak in the scenery, and the spacious porch made the perfect setting for unforgettable family dinners while watching the sunset. The kitchen is exceptionally well-equipped, ideal for preparing large, home-cooked meals to share with loved ones. Check-in was seamless, and communication with the owner via WhatsApp was...
Villa Larniano, With Private Pool And View On Vineyard

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool

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

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

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

10.0 out of 10, Exceptional, (91)
"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

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

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

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

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (36)
"My family of 7 had a lovely stay at il Boschetto. The house is as described with well- loved and charming older furniture. We didn't care. We had plenty of room to spread out.The view from the upstairs windows is beautiful. We knew the pool would not be open yet, but still spent time with cocktails out in the yard and enjoyed walking the property (saw wild boar, quail, owls!). My son cooked dinner on the outdoor brick grill. We had some chilly weather and made a fire in the living room. Michael...
Il Boschetto an oasis of peace and nature in Siena

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!

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!

Exclusive villa with park and private swimming pool in Siena

6.0 out of 10, (2)
"Villa was not as advertised, stayed the night of arrival and then transferred to a property with a ground pool unlike this villa "
Exclusive villa with park and private swimming pool in Siena

Podere San Carlo, Siena, Siena and Chianti

Podere San Carlo, Siena, Siena and Chianti

Stunning private villa with WIFI, private pool, TV, patio, panoramic view, parking, close to Siena

10.0 out of 10, Exceptional, (15)
"Die Villa befindet sich in einer wunderbaren typischen Toskana Gegend. Objekt ist problemlos erreichbar am Ende über eine unbefestigte Strasse zwischen Reben und Zypressen. Simonetta ist sehr nett und half uns jederzeit falls Probleme bestanden."
Stunning private villa with WIFI, private pool, TV, patio, panoramic view, parking, close to Siena

Villa Montelisi, With The most Unique View On Siena (6km)

10.0 out of 10, Exceptional, (68)
"A group of 6 friends. Each couple had their own bedroom and bathroom. There was also a half bath. Very positive experience. Loved the Tuscan villa and beautiful scenery from each room. The wine tasting experience was excellent. Staff were very helpful. Recommend it highly. Would come back again!"
Villa Montelisi, With The most Unique View On Siena (6km)

Villa Colombaio, Country-house In Wine Estate 5km from Siena

10.0 out of 10, Exceptional, (15)
"A true tuscan experience in the hills of Sienna. Located on a vineyard, this complex of homes spread out through the huge property offer privacy and memorable views. A car is required as taxi service is scarce, and restaurants are a 10 minute drive away. Lavinia and her family oversee the whole operation and are remarkable in their service. Our family will remember this property as the best part of our vacation."
Villa Colombaio, Country-house In Wine Estate 5km from Siena
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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Top Siena Hotel Reviews

Find out more about Siena

Find out more about Siena

Siena Villas information

Number of reviews
138
Accommodation
92 Villas
Lowest Price
€1,282
Highest Price
€1,282

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between €1,282 and €1,282 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 92 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.