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Featured Villas in Cavallari and around

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (34)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.

Panoramic villa in the Tuscan hills, near Florence, Wi-Fi and costs included.

9.8 out of 10, Exceptional, (67)
"We stayed in this beautiful villa for days- it was peaceful and perfect for a group. We were on iur 30th wedding anniversary trip which included a few weeks in Italy. This villa worked for our large group of family and friends. Nicola was informative and kept in contact with us making sure our stay was good. We took advantage of Lorenzo and his wine tour and dinner services- it was an amazing experience."
Panoramic villa in the Tuscan hills, near Florence, Wi-Fi and costs included.

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

10.0 out of 10, Exceptional, (88)
"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

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (136)
"Our family of 4, incl 2 teens really enjoyed the quick commute to the countryside after a busy day in Florence. House had 2 bathrooms, large bedrooms and enough space to spread out. Backyard view and patio space made meals outside a treat! Cable TV was a hit with the teens. Owner was very responsive…"
The price is €459
includes taxes & fees
22 Apr - 23 Apr
Luxury Villa in the Florentine hills

Authentic Tuscan country house, dating back to around the year 1000

9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic Tuscan country house, dating back to around the year 1000

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (46)
"We had a great stay here. All of us really enjoyed the location!"
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (11)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

10.0 out of 10, Exceptional, (69)
"everything about the villa is totally wonderful. perfect location, perfect grounds, perfect view, perfectly comfortable. and bianca is the dream host. i would definitelycome back!"
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (96)
"Peaceful, quiet, tucked away beautiful in the beautiful Tuscany area. Would stay there again. Excellent property!"
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (67)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Casa Farsetti - Exclusive villa with private pool between Siena and Florence

9.4 out of 10, Exceptional, (20)
"Wonderful 18th century villa, with farm kitchen. Cooked and cooked, ate and ate."
Casa Farsetti - Exclusive villa with private pool between Siena and Florence

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"We had a wonderful stay and this property provided a nice central location from which to explore the region. Information from Steve was timely and extremely helpful. "
Beautiful Villa With Panoramic Views near San Gimignano

Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!

10.0 out of 10, Exceptional, (34)
"The villa was wonderful for our family of 13. Paulo was very attentive to our many questions leading up to the trip . We were very glad that we made use of the daily breakfast . The food was wonderful . It was nice to have breakfast before we headed out for the day. We all enjoyed the pizza party, the kids enjoyed rolling their dough and cooking their pizza in a wood burning oven. We had an amazing experience "
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!

House consists of a "two-room" and a "trilocale", Valdarno Aretino

10.0 out of 10, Exceptional, (49)
"Santa & Giovanni were wonderful! Anything we needed help with they were always available. Even gave us a ride to the train station! Fresh fruit & vegetables were plentiful! The air conditioners worked very well. It was very hot while we were there for 5 1/2 weeks. The pool was very refreshing. They even cooked for us along with their son & daughters help. We would definitely recommend you staying at this lovely home. It was very private, but the town was only 5 minutes away. "
House consists of a "two-room" and a "trilocale", Valdarno Aretino

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano

Exclusive villa with park and private swimming pool in Siena

10.0 out of 10, Exceptional, (1)
"Ottima esperienza accompagnata dalla cordialità dei proprietari. La villa è una comoda base per visitare Siena e i dintorni. Al rientro si può godere della piscina e del panorama delle colline tra gli ulivi. La proprietaria è un'ottima cuoca se si desidera una vera cena toscana"
Exclusive villa with park and private swimming pool in Siena

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of 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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Other property types in Cavallari

Fattoria il Milione Agriturismo

4.0 star property
8.2 out of 10, Very good, (177)
"The property gives you a true authentic Italian experience. It’s very charming and the view is awesome! The restaurant is incredible! "
The price is €116
includes taxes & fees
27 Apr - 28 Apr
Fattoria il Milione Agriturismo

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (154)
"Fabulous property and staff. Rita was so helpful when our car had to be towed, we wouldn't have been able to continue our trip with out her and the other team members help. The people here are amazing."
The price is €180
includes taxes & fees
22 Apr - 23 Apr
Il Battistero Siena - Residenza d'Epoca
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.

Frequently asked questions

How much do villas in Cavallari cost?
You’ll pay between €459 and €459 per night for a villa in Cavallari. No matter your budget, a fantastic escape is just 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 Cavallari?
Cavallari has 1556 villas to select from. Find a place that’s right for you quickly and easily by selecting the “Villa” checkbox under the “Property type” tab in our handy filter tool.
Why book your villa in Cavallari with Expedia?
Booking a villa in Cavallari is as easy as working out your travel dates and selecting an option that checks your boxes. Searching for something luxurious or affordable, or a stay that also offers free WiFi? Use Expedia’s search filters to narrow your results and find the perfect fit.