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1 Aug - 3 Aug
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8 Aug - 10 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured 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
Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service
Enjoy dining al fresco amidst lush greenery and warm ambiance.

Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service

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 NZ$3,273
includes taxes & fees
31 July - 1 Aug
Exclusive Villa 20 minutes to Florence center w/ heated pool & Concierge service
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
Enjoy a peaceful retreat in a charming stone cottage with an outdoor seating area and grill.

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
Relax by the serene pool surrounded by lush greenery and olive trees.

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
Relax by the serene pool surrounded by lounge chairs and tables under a large tree.

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.
Surrounded by lush greenery and vineyards, this house offers a tranquil environment.

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (37)
"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
Experience the serene blend of old-world charm and modern art in this tranquil outdoor setting.

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.
Relax by the serene pool surrounded by lush greenery and flowering plants, with lounge chairs for ultimate relaxation.

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

10.0 out of 10, Exceptional, (113)
"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
Relax in this serene outdoor seating area, surrounded by lush greenery and a picturesque countryside view.

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
Relax by the serene pool surrounded by lush greenery and a bubbling jacuzzi.

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
Set amidst lush greenery and olive groves, this property offers a serene outdoor space with a swimming pool and sun terrace.

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
Relax by the pool surrounded by a lush garden and comfortable patio seating.

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
Cozy living room with a traditional fireplace, comfortable seating, and a television.

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 2 -10 guests
Relax by the serene pool, surrounded by lush trees and distant hills.

Villa Cicogna Private Villa, sleeps 2 -10 guests

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!"
Villa Cicogna Private Villa, sleeps 2 -10 guests
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Stroll through this elegant hallway, featuring a potted plant, a vase of flowers, and a framed mirror.

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.
Relax by the serene pool surrounded by lush greenery and Mediterranean architecture.

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.
Relax by the pool surrounded by lush greenery and comfortable seating options.

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
Surrounded by lush forest and rolling hills, this historic building offers a serene and secluded environment with a garden and outdoor pool.

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
Escape to a serene countryside retreat surrounded by lush greenery and cypress trees, with a lawn and swimming pool.

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

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"My friend and I had such a relaxing time at Relais!! We both got amazing massages from Natalie, the staff helped me figure out how to get to Rome after, the rooms were GORGEOUS, the pool was spectacular and got great poolside drinks, and the food/wine was the best!!! Stay here for a romantic and relaxing getaway surrounded by Tuscany’s beautiful rolling hills and vineyards. Would definitely come back!"
mary 1-night trip
Posted 7 days ago
Relais Vignale & Spa

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between NZ$3,273 and NZ$3,273 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.