Search Villas in Chianti Region

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Chianti Region Villas

Relais Badia a Passignano
Land view from property

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
Stunning stone building with a large arched doorway and windows, set amidst a charming entrance.

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 £1,404
includes taxes & fees
1 Sept - 2 Sept
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
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
Luxury Villa Basilio Chianti
Seasonal outdoor pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti
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, (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.
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
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Standalone residence with a traditional Mediterranean architectural style, surrounded by lush greenery.

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 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 serene pool surrounded by lush greenery and trees.

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
Relax by the pool with comfortable lounge chairs and a wicker basket for your essentials.

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

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 pool surrounded by lush greenery 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!"
The price is £113
includes taxes & fees
7 Aug - 8 Aug
Villa Cicogna Private Villa, sleeps 2 -10 guests
EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE
An outdoor event space with a stone-paved area, white chairs, and a white tent, set amidst lush greenery and trees.

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
Villa Andressa Grande: A spacious and welcoming age-old estate in the characteristic style of the Tuscan countryside, with Free WI-FI.
Traditional stone building with a rustic charm, surrounded by lush greenery and a covered patio area.

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.
Tenuta Pian Del Gallo, Greve in Chianti, Florence and Chianti
Relax by the serene pool surrounded by lush greenery and rolling hills.

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

Tenuta Pian Del Gallo, Greve in Chianti, Florence and Chianti
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Relax by the serene pool surrounded by lounge chairs and lush surroundings.

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 Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.
Relax by the serene pool surrounded by lush greenery and expansive countryside 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
Property grounds

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
Relax by the serene pool surrounded by lush greenery and vibrant flowers.

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
Surrounded by lush greenery, this traditional building offers a serene natural setting with multiple levels and windows.

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chianti Region Hotel Reviews

COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Beautiful!"
Julie 4-night trip
Posted 2 days ago
COMO Castello Del Nero