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Compare 578 Villas in Chianti Region with updated reviews, rates, and availability.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (47)
"My wife and I both loved this property. The host (Gianni) was responsive to any questions we had. Gianni's parents (Carlo & Paula) live in the adjacent main house and were extremely hospitable. We honestly couldn't have asked for a better location or host/s. We would recommend this property to anyone that wants to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

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.

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

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

9.8 out of 10, Exceptional, (27)
"We loved our stay at this authentic farmhouse ! The family was very , very warm and welcoming and attentive to our needs / questions. If you don’t have a car ( we didn’t ) you need transport and we had a driver / tour one day . We loved the home cooked meals by Barbara and the pre- stocked groceries. It is quite bare bones - don’t expect any paper towels , any extras at all , not even those you might expect past guests have left . There is literally nothing provided so you must purchase ....
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

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

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

10.0 out of 10, Exceptional, (108)
"We had the most wonderful time staying at this gorgeous property in early March. The property and house are absolutely gorgeous and extremely comfortable for a family (we were a group of adults, but the house and grounds are lovely for kids as well). But the real stars of the experience were Beatrice and Jacobo. They did everything they possibly could to make our experience wonderful - they prepared a delicious welcome meal for us on our arrival, did breakfasts every day, arranged rental cars...
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

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

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

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

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

9.8 out of 10, Exceptional, (98)
"This villa exceeded our expectations. It has ample room for a large family and was very neat and clean. The host was very attentive to all of our needs and very easy to communicate with. The location is just far enough away from Florence to give it a great Tuscan feel in the middle of a vineyard and olive orchard. I highly recommend this property. "
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

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

10.0 out of 10, Exceptional, (33)
"Villa Il Forte is the most incredible setting. It is an incredible historic and luxurious home while being comfortable, spacious and accommodating. Many different spaces to relax, connect and play. Paolo’s team were absolutely amazing. The chef Thomas is so talented while also being wonderfully personable and fun. The driver Fabrizio was so generous and thoughtful. His guides were knowledgeable and friendly. I have already booked it for next year! I can’t wait to go back! "
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

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"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

Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay at Le Vecchie Villa near Radda Italy. The views from our villa were magnificent, olive trees and vineyards surrounding the property. It's a bit of a steep climb on the unpaved road to the property so drive slow and steady. I'd recommend guests get a vehicle with a sufficient ground clearance to avoid the ruts on the road. We experienced some rain, so it was nice to stay in for the day and play games and sample our many Italian food delights purchased at the local Coop grocery...
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy

Villa Andrei, a relaxing bath in the Tuscan countryside with private pool

10.0 out of 10, Exceptional, (53)
"We spent almost two weeks in Tuscany and rented three houses. Villa Andrei was a highlight - an beautiful and quiet location. You are on your own and can really enjoy your time under the Tuscan sun. The surrounding landscape and the view are wonderful. We had plenty of space in the house and especially on the terrace. The pool was already very usable at the end of May and certainly a blessing in the height of summer. We would recommend Villa Andrei to anyone looking for a great stay near...
Villa Andrei, a relaxing bath in the Tuscan countryside with private pool

Elegant luxury villa near Florence with private pool and winery

10.0 out of 10, Exceptional, (42)
"Heaven with daily service and smiles. Marco and staff were superb. Strongly recommend "
Elegant luxury villa near Florence with private pool and winery

AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

10.0 out of 10, Exceptional, (10)
"Beautiful, quiet and peaceful."
AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

private Villa with A/C, Wifi, Swimming Pool in the heart of Chianti (Tuscany)

private Villa with A/C, Wifi, Swimming Pool in the heart of Chianti (Tuscany)

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

10.0 out of 10, Exceptional, (7)
"The house was great and Paula and Niccolo the best. Not a lot of restaurants nearby and you need to make reservations, but about 15 minuntes to Florence."
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
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 Chianti Region

Hu Norcenni Girasole Village

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

Relais Villa Olmo

9.4 out of 10, Exceptional, (204)
"Lovely hotel. Nice rooms - but a bit dark. The restaurant was very good and well priced. All of the staff was extremely helpful and accommodating. However without a car this hotel is quite isolated. The town nearby has very limited options for dining and shops."
The price is AED 674
AED 754 total
includes taxes & fees
15 Apr - 16 Apr
Relais Villa Olmo

Riserva di Fizzano Residence

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay and experience. The property is well maintained and very peaceful. Everyone on the staff is friendly and very excited to have you as a guest. Food was wonderful. 5 stars all around. Convenient location for day trips or to just relax by the pool. Highly recommend"
Riserva di Fizzano Residence
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 Chianti Region cost?
Villas in Chianti Region cost between and per night. These escapes offer the privacy of your own space at a price that doesn’t break the bank. 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 Chianti Region?
Chianti Region has 578 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
Why book your villa in Chianti Region with Expedia?
We think arranging a vacation should be a breeze, so if you’re looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.
How can I find cheap villas in Chianti Region?
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