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Featured Villas in Chianti Region and around

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

9.8 out of 10, Exceptional, (30)
"Local sights and food"
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

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

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (39)
"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.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is €2,277
includes taxes & fees
16 Aug - 17 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"Thank you for a fantastic experience - everything was just right."
Villa Casa al Sole Large Private Pool, WiFi

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 in Colle Di Val D’elsa with 7 bedrooms sleeps 14

9.8 out of 10, Exceptional, (7)
"My family and I stayed here for almost a full week in the spring, and had an amazing time. The host was extremely responsive about the check-in process leading up to the stay, during the stay whenever we had any issues, and even after our stay when we needed to recover an item that was left behind. There were some slight hiccups with the house during our stay (garage door opener was out of batteries one time and the shower drain clogged one time), but the host was proactive as can be and quick...
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14

Villa Andressa Grande: A spacious and welcoming age-old estate in the characteristic style of the Tuscan countryside, with Free WI-FI.

Villa Andressa Grande: A spacious and welcoming age-old estate in the characteristic style of the Tuscan countryside, with Free WI-FI.

EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE

10.0 out of 10, Exceptional, (70)
"Everything was as good or better as the pictures! Beautiful location and the villa was perfect. Cinzia was very helpful in getting us names of drivers and a chef. "
EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

10.0 out of 10, Exceptional, (10)
"Podere Ferrale is just amazing. We were a group of 8 people and Sam was an amazing host from start to finish. Our parents had big birthdays and Sam and her husband cooked a wonderful dinner for them. We would definatley come back!"
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.

Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.

Villa Poggio la Croce by MMega

Villa Poggio la Croce by MMega

Casa Lucia - Holiday Villa Rental with swimming pool on the hills of Chianti, Tuscany

10.0 out of 10, Exceptional, (61)
"Amazing Location Of Villa."
Casa Lucia - Holiday Villa Rental with swimming pool on the hills of Chianti, Tuscany

La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

10.0 out of 10, Exceptional, (1)
"This was a lovely rental in Chianti! The space was clean and had everything we needed for an enjoyable and comfortable stay! The hosts are so friendly and the property had such amazing sculpture and art. "
La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

Torretta Barbischio, Gaiole in Chianti, Siena and Chianti

10.0 out of 10, Exceptional, (4)
"Beautiful house in a cozy village in the heart of Chianti. The garden with pool is stunning and the house is very well restored and perfect to enjoy a relaxing vacation. Truly raccomended "
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti

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

10.0 out of 10, Exceptional, (76)
"Bianca was the perfect host. She communicated quickly and clearly. She was so eager to help and spend time with us as we inquired about the region. She was super helpful to help arrange transportation and give us good insight to our visit. The property is in a great loction. Close to Florence yet out in the fields of Tuscany. There were ten of us and the villa worked so well. We all would go back to the villa and Bianca."
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

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

10.0 out of 10, Exceptional, (60)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
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 Chianti Region Hotel Reviews

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between €2,277 and €2,277 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 540 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 holiday 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.