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Compare 369 Vacation Homes in Chianti Region with updated reviews, rates, and availability.

Wonderful Tuscan farmhouse with large spaces and panoramic views
Room

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
Holiday home in the Florentine Chianti half an hour from Florence
Property grounds

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

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

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.
[Chianti] Riccimballa Luxury Penthouse
Exterior

[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
House on Florence Hills - 4 Miles Away from Downtown Florence!
The 'Calcio Storico' bedroom with its canapy double bed

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!
Casa Elena Panoramic Chianti Hills, Greve in Chianti, Italy
Detached House

Casa Elena Panoramic Chianti Hills, Greve in Chianti, Italy

Casa Elena Panoramic Chianti Hills, Greve in Chianti, Italy
Agriturismo La Ferrozzola
Exterior

Agriturismo La Ferrozzola

9.4 out of 10, Exceptional, (9)
"Are you still available? I want to bring my whole family:)"
The price is SAR 466
SAR 528 total
includes taxes & fees
6 Jan - 7 Jan
Agriturismo La Ferrozzola
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi
Pool

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

The price is SAR 1,345
SAR 1,825 total
includes taxes & fees
7 Jan - 8 Jan
Holiday Home "Altrove" with Private Pool, Private Terrace & Wi-Fi
Casa Da Vinci for two
Room

Casa Da Vinci for two

8.0 out of 10, Very Good, (1)
"Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend."
Casa Da Vinci for two
Wonderful villa for 6 people with private pool, A/C, WIFI, TV, patio, pets allowed and parking
Golf, Outdoor, Pool, Summer

Wonderful villa for 6 people with private pool, A/C, WIFI, 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 "
Wonderful villa for 6 people with private pool, A/C, WIFI, TV, patio, pets allowed and parking
House with character in typical medieval borgo on the Chianti Classico hills
Exterior

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
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Pool

Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena

10.0 out of 10, Exceptional, (52)
"We loved this home. It has a large family area and three very private bedrooms, each with their own assigned baths. The rooms were spacious, clean and the beds were comfortable. Two rooms had queen beds and the third had 2 twin beds. The owner was amazing, walking us through the home plus providing amazing guidance on what to do, where to go and how to travel. This was absolutely best place and will definitely consider again when we travel back to Italy. Only thing to add would be a...
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Vacation home Tara by Interhome
House

Vacation home Tara by Interhome

8.8 out of 10, Excellent, (8)
"Beautiful guesthouse! Kitchen had everything we needed. Bigger bath towels would have been better. Difficult to communicate with the landlords as they had no English and I had very little italian"
Vacation home Tara by Interhome
Farmhouse in the heart of the real chiantishire
Entrance

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (129)
"What can we say!!! We loved the little house….so much charm! The hosts were very easy to communicate with….the quietness and beauty of the property were just what we needed!! "
Farmhouse in the heart of the real chiantishire
Villa with large garden in the Chianti hills
Pool

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

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.
House in a typical village in the heart of Chianti
Exterior

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
House in a typical village in the heart of Chianti
Exterior

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

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
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
Aerial view

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 "
Relais Villa Olmo
Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
Relais Villa Belvedere
Outdoor pool

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 329
SAR 368 total
includes taxes & fees
5 Feb - 6 Feb
Relais Villa Belvedere
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.