Search Vacation Homes in Chianti Region

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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 AED 634
AED 880 total
includes taxes & fees
23 Mar - 24 Mar
Chianti Craft House Badia a Passignano

The Photographer's House

9.8 out of 10, Exceptional, (9)
"The house is spacious, interesting and has everything needed for a holiday. The garden is a huge bonus - room to relax with a view (and grapes on the vine!). It was a joy to stay in an historic house in such an interesting town, with shops and restaurants within easy walking distance. We had a delicious meal at the owner’s restaurant too."
The Photographer's House

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 AED 1,476
AED 1,952 total
includes taxes & fees
21 Mar - 22 Mar
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi

Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

8.8 out of 10, Excellent, (10)
"The house has lots of space. We liked the area around and specially Home Restaurant near by the house "
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

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

[Chianti] Riccimballa Luxury Penthouse

10.0 out of 10, Exceptional, (1)
"The location is amazing. House is surrounded by hills and valleys. Perfect view of Tuscany. Plenty of amenities. Very spacious and clean house. Stay is on the second floor so be prepared to carry the luggage. There are two bathrooms but only one shower. The shower drain was not properly draining so was a bit of an inconvenience since we were 8. Good for smaller groups. Highly recommend this stay. I was there during the end of March, was a bit chilly but I am sure it will be more beautiful in...
[Chianti] Riccimballa Luxury Penthouse

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 guests with private pool, WIFI, A/C, 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 guests with private pool, WIFI, A/C, 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.
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.
Don't see what you're looking for?
See all available properties in Chianti Region
Save an average of 15% on thousands of hotels when you're signed in

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 AED 408
AED 460 total
includes taxes & fees
27 Feb - 28 Feb
Relais Villa Olmo

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

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.