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Compare 372 Vacation Homes in Chianti Region with updated reviews, rates, and availability.

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (131)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"The apartment is at the heart of the small village, central to several great restaurants and practically across the street from the incredible 11th century abbey. The place was very clean and has been recently renovated, but still had a very historic feel to it. Emanuel, our host, was very friendly and gracious. He offered several personal recommendations to restaurants and a wine tasting at a nearby castle, all of which were great! Would definitely stay here again!"
The price is SAR 639
SAR 887 total
includes taxes & fees
8 Feb - 9 Feb
Chianti Craft House Badia a Passignano

Holiday home in the Florentine Chianti half an hour from Florence

9.8 out of 10, Exceptional, (52)
"My wife and I spent nine nights is this spacious and well-equipped home in the quiet village of Montespertoli in the Chianti region of Tuscany. Bruno was a wonderful host, always quick to respond to our questions. He left the home equipped well for our first night or two and directed us to the Co-Op grocery store only a 3-4 minute walk from the front door. Our rental car was securely parked in his garage every night, so no need to park on the street or worry about not finding a place close to...
Holiday home in the Florentine Chianti half an hour from Florence

Wonderful Tuscan farmhouse with large spaces and panoramic views

10.0 out of 10, Exceptional, (11)
"We had a great time. The vila was everything we expected and our host was very accessible. I would highly recommend."
Wonderful Tuscan farmhouse with large spaces and panoramic views

House with swimming pool. Medieval village in the heart of Chianti Classico

10.0 out of 10, Exceptional, (106)
"Nice townhouse in a wonderfully centralized area. We wanted to explore the Chianti region from a 'home-base' and the Castellina in Chianti area was ideal for us."
House with swimming pool. Medieval village in the heart of Chianti Classico

House on Florence Hills - 4 Miles Away from Downtown Florence!

9.8 out of 10, Exceptional, (41)
"The place was rustic and relaxing. Far away from thr city center so you will need transportation. The driving service was very expensive but worth it for the trip."
House on Florence Hills - 4 Miles Away from Downtown Florence!

Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi

The price is SAR 1,495
SAR 1,977 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi

A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>

10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed this beautiful cottage, which has been lovingly built and maintained by Carlo. It is close enough to Florence for easy day trips - a car is recommended for convenient access to the property, but there is ample free parking in a nearby town to head downtown by bus. Accommodations were very comfortable, we made good use of the fridge and convection cooktop, and the views are unmatched. Carlo was kind and quick to respond with any questions we had. Pro tip for those not...
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>

country house with garden ,pool,children's play area ,Tuscany,15 from Florence

9.8 out of 10, Exceptional, (79)
"The place was everything we wanted and more. The perfect size house, beautiful grounds and pool, and I can’t imagine a better town (San Casciano) to be based out of. Sonia was the most wonderful host, giving us amazing information about the town and things to do in the area that we would have not found otherwise. We can’t recommend this place more highly!!!!"
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Beautiful Tuscan Home Santa Margherita, Bucine, Italy

Beautiful Tuscan Home Santa Margherita, Bucine, Italy

Casa Elena Panoramic Chianti Hills, Greve in Chianti, Italy

Casa Elena Panoramic Chianti Hills, Greve in Chianti, Italy

Beautiful villa for 6 people with A/C, WIFI, private pool, TV, patio, pets allowed and parking

9.8 out of 10, Exceptional, (8)
"Très bien installés afin de faire de super ballades Merci nous avons passé un très bon séjour "
Beautiful villa for 6 people with A/C, WIFI, private pool, TV, patio, pets allowed and parking

House in a typical village in the heart of Chianti

9.4 out of 10, Exceptional, (34)
"It's a great home base to start exploring the region. Two wineries are very close by, and Florence is an easy drive away. The traditional way the house is built keeps it nice and cold during the day. We loved it!"
House in a typical village in the heart of Chianti

House in a typical village in the heart of Chianti

9.6 out of 10, Exceptional, (68)
"Our 2 bedroom apartment was beautiful in every way. Perfect location, accommodations, and atmosphere for a 5 day holiday away from crowds. We loved it. The owners were friendly and helpful."
House in a typical village in the heart of Chianti

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

9.8 out of 10, Exceptional, (72)
"The house is picture perfect - and the views are absolutely stunning. As others have said, to get to it, you need to drive down a bit of bumpy dirt road (so having a SUV would be a wise choice), but once you get there l, the pure serenity and peacefulness of the Tuscan hills await you. It was so relaxing and quiet and really felt like you had it all to yourself. The house itself was great - 4 large bedrooms and 2 large bathrooms (especially for European standards) provided plenty of space to...
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

House with character in typical medieval borgo on the Chianti Classico hills

9.6 out of 10, Exceptional, (47)
"Our three year old granddaughter thought it was her castle and that she was a princess. Michele and Elisabetta remain exquisite hosts and the neighbors are very welcoming. Rental cars and train system allowed us to visit neighboring cites. Overall, a wonderful vacation!!!!"
House with character in typical medieval borgo on the Chianti Classico hills

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

8.8 out of 10, Excellent, (19)
"Waking up in the morning to the Tuscan sun rising above the surrounding hills was a magical moment I will never forget. The view from the front yard of the property was panoramic and picturesque. It almost made me forget how hard it was to find the place in the dark, with inadequate directions. Almost. If I had to do it over again, I’d arrive late afternoon in the daylight. The property is only accessible through a rugged dirt road. Also the address given didn’t work in my Maps app. Only when I...
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Chianti Holiday House, private jacuzzi up to 6 pax

9.4 out of 10, Exceptional, (19)
"• Pros: Beautiful grounds, garden and hot tub; dishwasher was greatly appreciated, lovely views, excellent Instructions to reach the village. Cons: • Internet/cell connectivity in village is poor and upon arrival, couldn’t connect with cell phone OR my portable wifi. I couldn’t reach the owners, and had no photos to identify the house was ours, and instructions were incomplete. Had to knock on doors which was awkward. • Password for the wifi is wrong. Passwords are case-sensitive! This wasted a...
Chianti Holiday House, private jacuzzi up to 6 pax

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

10.0 out of 10, Exceptional, (9)
"Villa was the perfect place. Marco our host was very attentive and helpful. Space for all 27 to relax and have fun from ages 3 to 76. Food by private chef delicious. Pool great size and vey clean. Loved hiking around the grounds. Good location for all family members to make daily excursions. Wine tasting and tour excellent. Accommodations were wonderful…we were there at the hottest time so Marco help with an in room AC and many fans for the third floor. It all worked out."
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Villa with large garden in the Chianti hills

9.4 out of 10, Exceptional, (69)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills
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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Other property types in Chianti Region

Relais Villa Olmo

9.4 out of 10, Exceptional, (200)
"My family and I stayed there for 2 nights, at the family suite. It was very clean and well decorated & furnished, with private pool and garden. The environment and view were good, staff were helpful, buffet breakfast got lot of choices. Highly recommended this lovely place "
The price is SAR 334
SAR 379 total
includes taxes & fees
25 Feb - 26 Feb
Relais Villa Olmo

Relais Villa Belvedere

9.2 out of 10, Wonderful, (64)
"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."
The price is SAR 349
SAR 389 total
includes taxes & fees
6 Feb - 7 Feb
Relais Villa Belvedere

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
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.