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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Featured Villas in Chianti Region

Our top choices for Chianti Region villas

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

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

9.8 out of 10, Exceptional, (103)
"Villa was great. Picturesque countryside. Very comfortable for 4 adults and 2 kids using 4 bedrooms. Could have easily had more ppl. Location very convenient to Florence and surrounding area. Host was very kind and had lots of info about the area and how to navigate Florence as a tourist."
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (2)
"Très belle propriété en pleine campagne. Très bien amenagée, beaucoup d’equipements, tout était très propre, notre hote Frederico a notre écoute. Piscine à debordement magnifique avec une vue splendide. Nous étions au calme. Seul bémol le chemin pour arriver à la propriété. Nous gardons cette adresse pour une prochaine viste dans quelques années."
Private villa in the heart of chianti with view of siena
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Outdoor pool

SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI

10.0 out of 10, Exceptional, (5)
"Amazing location with everything you need for a relaxing and pleasant stay! Uncomplicated check-in and check-out, fast replies to any questions. Thanks a lot Arianna and Natale!"
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor pool

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

9.6 out of 10, Exceptional, (23)
"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
Seasonal outdoor pool

Luxury Villa Basilio Chianti

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

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

10.0 out of 10, Exceptional, (118)
"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.
Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!"
Your panoramic house in Tuscany between vineyards and olive groves.
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
Exterior

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

10.0 out of 10, Exceptional, (80)
"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
Relais Badia a Passignano
Land view from property

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Elegant luxury villa near Florence with private pool and winery
Property grounds

Elegant luxury villa near Florence with private pool and winery

10.0 out of 10, Exceptional, (44)
"Beautiful historic villa, lovely garden, great service, excellent wines and olive oil!"
Elegant luxury villa near Florence with private pool and winery
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Exterior

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (56)
"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
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Outdoor dining

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

9.8 out of 10, Exceptional, (38)
"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!
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
Outdoor dining

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

9.8 out of 10, Exceptional, (31)
"Local sights and food"
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
VILLA GIOTTO, FLORENCE
Outdoor pool

VILLA GIOTTO, FLORENCE

9.8 out of 10, Exceptional, (7)
"We were a group of six who had the pleasure of staying in this beautiful villa with an absolutely stunning property with a large pool and outdoor living area. Our favourite night was having Bernardo come and make a traditional Tuscan dinner for us including bruschetta, pasta which was the best we had while travelling through Italy, chicken with a beautiful salad and classic tiramisu. What a spectacular evening to close out an amazing stay at this villa. To get around easily we recommend highly...
VILLA GIOTTO, FLORENCE
Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning
Exterior

Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning

10.0 out of 10, Exceptional, (1)
"Absolutely stunning. Every detail was taken care of. This home and property exceeded what you see in the photos. "
Villa 'Beccalorzo' with Private Pool, Wi-Fi and Air Conditioning
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor pool

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."
The price is AU$2,330
includes taxes & fees
15 Sept - 16 Sept
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
Pool

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

9.8 out of 10, Exceptional, (8)
"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.
Exterior

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 Zambra by MMega
Outdoor dining

Villa Zambra by MMega

10.0 out of 10, Exceptional, (1)
"Beautiful villa in an ancient tower! Immaculate and beautifully furnished Easy commute to Tuscany points of interest"
Villa Zambra by MMega
Villa Poggio la Croce by MMega
Property grounds

Villa Poggio la Croce by MMega

8.0 out of 10, Very good, (1)
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

Find out more about Chianti Region

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
Accommodation
495 Villas
Lowest Price
AU$2,330
Highest Price
AU$2,330

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do villas in Chianti Region cost?
Prices for villas in Chianti Region range between AU$2,330 and AU$2,330 per night. No matter your budget, you're sure to find a place that fits your needs on Expedia. This price was 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 pick from. Enter your travel dates and destination and organise your perfect stay today.
What is there to do near my villa in Chianti Region?
One of the most important travel accessories for your Chianti Region adventure is an epic itinerary! Colle di Val dElsa Cathedral, Sentierelsa Trail and Piazza Arnolfo di Cambio are some of the top sights if you're visiting Val dElsa. San Gimignano is also home to fantastic attractions, such as Sovestro in Poggio Winery. Eager to add to your to-do list? Drop by Museo Civico and Museum San Gimignano 1300 too.