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Featured Villas in Chianti Region

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

10.0 out of 10, Exceptional, (115)
"It was a great experience. The villa was perfect. Hosts were amazing. "
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

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.

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

9.8 out of 10, Exceptional, (103)
"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

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

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

9.4 out of 10, Exceptional, (65)
"Beautiful location!"
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Elegant luxury villa near Florence with private pool and winery

10.0 out of 10, Exceptional, (43)
"Heaven with daily service and smiles. Marco and staff were superb. Strongly recommend "
Elegant luxury villa near Florence with private pool and winery

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"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 NZ$3,612
includes taxes & fees
26 Aug - 27 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, (21)
"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.

Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax

9.8 out of 10, Exceptional, (64)
"Relaxing stay in beautiful surroundings, visited Panzano and Sienna. Would highly recommend."
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax

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.

10.0 out of 10, Exceptional, (1)
"Villaen og lokationen var fantastisk, hvilket gjorde opholdet vidunderligt.Wifi bør forbedres med stærkere hastighed og routers opppe og nede i huset, evt. også udenfor. Til tider virkede internettet slet ikke.Indkøb et par skåle til salalt, pasta, etc. og flere teskeer."
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
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 NZ$3,612 and NZ$3,612 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 495 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
What is there to do near my villa in Chianti Region?
Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.