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Featured Villas in Cavallari and around

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (92)
"Lovely large 4 bedroom house with spectacular views of San Gimignano. Really enjoyed our stay and highly recommend this rental. Everything was perfect including the pool. Alessandro "
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Luxury Villa in the Florentine hills
9.8 out of 10, Exceptional, (127)
"My wife and I chose this Villa based on the location as well as the pictures provided in the advertisement. The location was absolutely fabulous. My son and daughter in law joined us the first week, and all the excursions in the Tuscon region were within a hour to an hour and a half drive from the Villa. It was very convenient. Also there are a couple very small towns nearby where we did our grocery shopping as well as small specialty shops and restaurants. The Villa was very clean and had...
Luxury Villa in the Florentine hills
Tailored stay・Villa w/ heated pool, concierge service, 8 mile to Florence Center
10.0 out of 10, Exceptional, (94)
"Our group of 10 just checked out of the villa today. Five couples from the USA and we were all extremely pleased with our accommodations and time spent in the region of Impruneta. Our hostess, Caterina and her family were responsive to every question whether it was local restaurants, local tours of pottery, specific Florence Shopping options, parking or train schedules. We utilized almost every area of the Villa specifically the clean and refreshing swimming pool, ping pong table and well...
Tailored stay・Villa w/ heated pool, concierge service, 8 mile to Florence Center
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (79)
"This was our second villa rental in the San Gimignano area, our first at Alessandro's villa and it was amazing! Alessandro was very responsive and helpful from the moment we booked the year prior, until the day we checked out. We were a group of 6 adults and had plenty of room. The villa has every amenity you might need during your stay. At check in Alessandro provided us with helpful information about the surrounding area. The villa is in a beautiful setting surrounded by vineyards and olive...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
10.0 out of 10, Exceptional, (40)
"There were seven of us staying for three nights in July 2024. It was simply amazing in every way. It was a highlight of our Italy experience. The location is in a great location for adventuring in Tuscany, but we had so much fun at this house. We used the pool, outdoor seating areas (numerous), grill, and games everyday. The house, bedrooms, and bathrooms were really nice too. So quiet and private, the grounds were so pretty. Speaking of which, you are nestled in the middle of gardens, fruit...
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
Beautiful villa with private pool immersed in the Tuscan countryside
10.0 out of 10, Exceptional, (103)
"The property is an authentic Tuscan dream and the view is so stunning it is almost unreal. Francesca is an excellent host whose personal history with the house shines through in her attentiveness and care of her guests and their experience while visiting. 100% recommended."
Beautiful villa with private pool immersed in the Tuscan countryside
15th century barn fully renovated in a stylish style with gorgeous swimming pool
10.0 out of 10, Exceptional, (4)
"The renovated barn has been lovingly and tastefully transformed into a beautiful Tuscan villa—the perfect base for our family’s first visit to the area. The space is truly unique in all the ways it has incorporated modern design and amenities while preserving the rustic charm of the structure. The rooms and furnishings are comfortable, and the kitchen is a great place to prepare a meal with fresh local ingredients. The location was ideal for our itinerary, as we could easily visit Siena and San...
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Villa luna with pool and garden near the center of Siena
8.8 out of 10, Excellent, (25)
"Wonderful location. Loved the view, the pool, the outdoor bbq area"
Villa luna with pool and garden near the center of Siena
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Luxury Villa with large pool close to Florence
10.0 out of 10, Exceptional, (61)
"This villa is spectacular. Panoramic views are breathtaking. The villa is beautiful and perfectly maintained. The pool was great. Best of all the hosts live there as well. They are wonderful people. So helpful and friendly. Fonsy is a Fantastic chef who prepared outstanding meals for our family. Our stay was perfect. I had dreamed of renting a villa for many years. This was even better than I could have dreamed. Definitely recommend Il Faeto to live your Tuscan dream. Our three...
Luxury Villa with large pool close to Florence
Beautifully restored Tuscan villa, with private pool and breathtaking views
10.0 out of 10, Exceptional, (14)
"Podere Macchione was the perfect place for our family gathering in Tuscany. Cally was an absolutely incredible host who looked after every detail, and whose home was a little bit of heaven on earth for us to enjoy. Everything, from the “out of this world” views, to the beautiful interior design, to wine tasting with Emily, and to a classic Tuscan dinner with Massi, was perfect. We will cherish this vacation, and have, in large part, Cally to thank for it!!!"
Beautifully restored Tuscan villa, with private pool and breathtaking views
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Villa Feudo, incredible villa with private pool and park, located in Cerbaia, in the Tuscan coun...
10.0 out of 10, Exceptional, (6)
"Great location, close to Florence. Comfortable beds."
Villa Feudo, incredible villa with private pool and park, located in Cerbaia, in the Tuscan coun...
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
9.6 out of 10, Exceptional, (16)
"We enjoyed a delightful two weeks staying at Villa Il Borrachio in September. Apartment Azalea is spacious, well equipped and set on two floors. The two bedrooms on the first floor have double beds and en-suites whilst the bedroom on the ground floor has two single beds with a bathroom located on the other side of the kitchen/dining area. There is a wonderful view from the living room of the countryside with San Gimignano in the distance. The wi-fi was good and with our laptop plus hdmi cable we...
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
9.0 out of 10, Wonderful, (2)
"Très belle maison et cadre agréable "
Villa in Gambassi with pool, A/C, village and restaurant at walking distance,
Villa Casa al Sole Large Private Pool, WiFi
9.8 out of 10, Exceptional, (18)
"This is a beautiful villa with plenty of space for our large group. It is in a remote location and very quiet. It was perfect for short trips to local towns and then a swim in the afternoon. We spent most evenings on the patio enjoying the Tuscan sunsets. We would definitely stay again! "
Villa Casa al Sole Large Private Pool, WiFi
Villa Radda by MMega
10.0 out of 10, Exceptional, (4)
"Perfect family getaway tucked into the olive groves with stunning vistas."
Villa Radda by MMega
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE
10.0 out of 10, Exceptional, (44)
"It was absolutely marvelous. The owner of the property was so informative on places to visit, and places to eat etc. We had a wooden time and I would recommend that everyone stay here at least once in your lifetime."
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE
Apartments Florence - Villa Fonte Morgana with pool
Apartments Florence - Villa Fonte Morgana with pool
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
8.0 out of 10, Very good, (2)
"This house is very nice. It is centrally located outside Siena and good location to explore all over Tuscany. It is off the beaten path so you’ll definitely need a rental car. Even just to get there. It is remote. Which is a plus but also has some drawbacks. We went in March so pool was closed. Too cold to swim. House is several levels. Kitchen and dining room are downstairs. We cooked several simple meals after going into town to grab groceries. Nearby town is nice. Not a lot of restaurant...
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
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Other property types in Cavallari

Fattoria il Milione Agriturismo
3.0 star property
8.2 out of 10, Very good, (154)
"Thankyou so much for making this a lovely experience for our family. It was full of character "
The price is €108
includes taxes & fees
28 Oct - 29 Oct
Fattoria il Milione Agriturismo
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, (274)
"Great stay with the family. Not good for handicapped "
The price is €60
includes taxes & fees
28 Sept - 29 Sept
Hu Norcenni Girasole Village
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, (37)
"Unit was nice- shook throughout the night strangely but almost felt like being on a ship. Limited hours for the pool and services. "
The price is €62
includes taxes & fees
24 Oct - 25 Oct
Camping Village Il Poggetto
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?
Prepare to pay between and per night for villas in Cavallari. No matter your budget, an ideal stay is just a click 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?
Pack your bags and pick from 1278 villas in Cavallari. For a family escape, a getaway with pals or anything in between, Expedia can help you find the perfect space in a few simple clicks.
Why book your villa in Cavallari with Expedia?
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How can I find cheap villas in Cavallari?
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