Search Vacation Homes in Chianti Region

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 448 Vacation Homes in Chianti Region with updated reviews, rates, and availability.

Wonderful Tuscan farmhouse with large spaces and panoramic views
2 bedrooms, internet, bed sheets

Wonderful Tuscan farmhouse with large spaces and panoramic views

10.0 out of 10, Exceptional, (15)
"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
The Porchereccia delle Bartaline
Exterior

The Porchereccia delle Bartaline

9.4 out of 10, Exceptional, (14)
"Great place and being in person is better than the on-line pictures. Beautiful views over looking the valley and vineyards below. Centrally located for plenty of great roadtrips. Enjoy!"
The Porchereccia delle Bartaline
Farmhouse in the heart of the real chiantishire
Exterior

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (135)
"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
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Outdoor pool

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

9.8 out of 10, Exceptional, (73)
"Perfect location for a family reunion with our adult children and their partners. We had a wonderful time."
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Property grounds

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany

9.6 out of 10, Exceptional, (47)
"A fantastic place to visit Tuscany from. The pool is great and the owners are very friendly."
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Chianti Craft House Badia a Passignano
Point of interest

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"This place was absolutely amazing. The family loved it."
The price is AED 665
AED 931 total
includes taxes & fees
8 May - 9 May
Chianti Craft House Badia a Passignano
Chianti Holiday House, private jacuzzi up to 6 pax
Outdoor spa tub

Chianti Holiday House, private jacuzzi up to 6 pax

9.4 out of 10, Exceptional, (19)
"We enjoyed our stay in Chianti. This home is very remote, 90 minutes from Florence up twisting mountain roads. Google maps got us within 2 km. The turn off to the rental from the main road is further west than Google shows on SP73. The nearest market is 30 km. It was a little confusing finding which building and door was ours, but hosts were asy to reach and very helpful through the VRBO messaging. They replied quickly to all my questions. The home was clean, and well stocked with extra pillows,...
Chianti Holiday House, private jacuzzi up to 6 pax
detached villa with private pool and garden
Pool

detached villa with private pool and garden

8.8 out of 10, Excellent, (20)
"We had a wonderful time in the nice little house on the quiet edge of a lively village, with spectacular Tuscany scenery, a super clean pool and friendly and helpful owners. Both Florence and Siena are fully worth a trip, or you just stay at the house for perfect relaxing."
detached villa with private pool and garden
Charming ancient farm house in Chianti
Interior

Charming ancient farm house in Chianti

9.6 out of 10, Exceptional, (43)
"The place wasreally great. We were a group of 8 People and one Baby. We had enough space in the house. The pool and the view was amazing. "
Charming ancient farm house in Chianti
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Outdoor pool, a heated pool

12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

10.0 out of 10, Exceptional, (21)
"Lovely place"
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Apartment House with garden Tuscany Chianti , Florence 15km.
Pool

Apartment House with garden Tuscany Chianti , Florence 15km.

9.8 out of 10, Exceptional, (72)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Apartment House with garden Tuscany Chianti , Florence 15km.
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
Property grounds

CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena

9.8 out of 10, Exceptional, (48)
"Elegant and high standard place, with a very friendly welcoming owner."
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

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
Outdoor dining

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

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)
"Very picturesque cottage in the countryside. Not too far from Florence but hard to navigate without a car. Owner was very kind and helpful and even gave us a ride to the train station at the end of our stay."
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>
House with views of the Chianti
Outdoor dining

House with views of the Chianti

House with views of the Chianti
The Fox - Comfort and luxury. Perfect location for your preciouse holidays
Interior

The Fox - Comfort and luxury. Perfect location for your preciouse holidays

10.0 out of 10, Exceptional, (1)
"A une demie heure de Florence, en plein Chianti, dans la nature, ce logement est plein de charme, très propre très agréable au calme, et la propriétaire très accueillante. On y a passé un excellent séjour ! (Petit conseil si vous avez une voiture un peu basse, pour y accéder la route n’est pas goudronnée)."
The Fox - Comfort and luxury. Perfect location for your preciouse holidays
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
Outdoor pool

Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti

9.6 out of 10, Exceptional, (64)
"The place is great, large appartement, great surroundings."
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
Sanlucchese 1
Miscellaneous

Sanlucchese 1

7.0 out of 10, Good, (2)
"Propriété bien distribuée dans un cadre champêtre très agréable Appartement spacieux avec de nombreuses baies vitrées donnant sur des terrasses. Attention chemin d’accès non goudronné avec de nombreuses ornières."
Sanlucchese 1
Capanna di Sopra by Interhome
Point of interest

Capanna di Sopra by Interhome

9.8 out of 10, Exceptional, (17)
Capanna di Sopra by Interhome
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

Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (284)
"Nice place for family time"
The price is AED 174
AED 204 total
includes taxes & fees
8 May - 9 May
Hu Norcenni Girasole Village
Camping Village Il Poggetto
Seasonal outdoor pool

Camping Village Il Poggetto

3.0 star property
8.0 out of 10, Very Good, (44)
"Nice safe village with restaurant, bar and pool. Staff were excellent. "
The price is AED 238
AED 270 total
includes taxes & fees
20 May - 21 May
Camping Village Il Poggetto
Relais Villa Olmo
Aerial view

Relais Villa Olmo

9.4 out of 10, Exceptional, (204)
"Lovely hotel. Nice rooms - but a bit dark. The restaurant was very good and well priced. All of the staff was extremely helpful and accommodating. However without a car this hotel is quite isolated. The town nearby has very limited options for dining and shops."
The price is AED 963
AED 1,072 total
includes taxes & fees
8 May - 9 May
Relais Villa Olmo
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.