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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Villas in Chianti Region

Relais Badia a Passignano
Seasonal outdoor pool

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
Outdoor dining

Made for gathering together, leave the rest to us - Villa 20 minutes to Florence

10.0 out of 10, Exceptional, (102)
"The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again "
The price is AED 6,214
AED 7,115 total
includes taxes & fees
Aug 20 - Aug 21
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
Outdoor dining

Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
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, (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
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, (1)
"Fantastiskt boende med underbar trädgård och utsikt, nära vingårdar och historiska städer!"
Private villa in the heart of chianti with view of siena
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, (38)
"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
Terrace/patio

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
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, (114)
"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.
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor dining

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
EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE
Outdoor pool

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
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Pool

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (48)
"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
Villa Casa al Sole Large Private Pool, WiFi
Pool

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

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 Cicogna Private Villa - sleeps 10 guests in 5 bedrooms
Pool

Villa Cicogna Private Villa - sleeps 10 guests in 5 bedrooms

10.0 out of 10, Exceptional, (5)
"Our family stayed here for a local wedding and enjoyed the charm of this quiet town and comfortable villa. The hosts were super responsive and welcoming, making sure we had everything we needed for a pleasant stay. Our toddler loved running around and swimming every day in the pool. The location is perfect to drive to nearby cities with parking provided. Would love to visit again!"
The price is AED 503
AED 503 total
includes taxes & fees
Aug 7 - Aug 8
Villa Cicogna Private Villa - sleeps 10 guests in 5 bedrooms
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Interior

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

10.0 out of 10, Exceptional, (9)
"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 Andressa Grande: A spacious and welcoming age-old estate in the characteristic style of the Tuscan countryside, with Free WI-FI.
Pool

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

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
Interior

Villa Poggio la Croce by MMega

Villa Poggio la Croce by MMega
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Exterior

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
Tenuta Pian Del Gallo, Greve in Chianti, Florence and Chianti
Dining

Tenuta Pian Del Gallo, Greve in Chianti, Florence and Chianti

Tenuta Pian Del Gallo, Greve in Chianti, Florence and Chianti
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

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"Nice room, great pool. Breakfast was good. "
Terry 3-night trip
Posted 3 days ago
Hotel Borgo di Cortefreda Relais

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between AED 503 and AED 6,214 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 584 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.