Holiday Homes in Chianti Region

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May 14 - May 15
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May 17 - May 19
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May 24 - May 26

Featured Holiday Homes in Chianti Region

Exterior
Belvilla by OYO Il Camino
10.0 out of 10, Exceptional, (1)
"We stayed for a week and this was one of our better holidays."
Belvilla by OYO Il Camino
Outdoor pool
RAFFAELLO - Firenze /Siena /San Gimignano - SWIMMING POOL AND TENNIS COURT
10.0 out of 10, Exceptional, (6)
"We had a such a wonderful visit. The house is very comfortable and very well equipped. The location is perfect for day trips to many interesting towns and beautiful sights. When not touring the views, pool, and tennis court can make for a relaxing day."
RAFFAELLO - Firenze /Siena /San Gimignano - SWIMMING POOL AND TENNIS COURT
Pool
STONE HOUSE IN THE HEART OF TUSCANY WITH LARGE GARDEN AND SWIMMING POOL
10.0 out of 10, Exceptional, (14)
"We had a brilliant stay with communication leading up to the holiday being excellent. Azzurra is such a lovely woman, very helpful and provided a beautiful house for us to stay in with everything you would ever need. Hairdryer, washing machine, dryer, iron & board, everything. Even the coffee capsules for the machine were all included. The house is brilliant, with a large master bedroom, smaller second room and double sofa bed downstairs. The garden area is stunning. 1000sq mts set over 3 tires....
STONE HOUSE IN THE HEART OF TUSCANY WITH LARGE GARDEN AND SWIMMING POOL
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TV, fireplace, DVD player
House with swimming pool. Medieval village in the heart of Chianti Classico
10.0 out of 10, Exceptional, (101)
"When we arrived the owner met us at the appartment and showed us around. His communication with us was great leading upto our arrival. The setting of this place is absolutely amazing. So quiet and beautiful. The views from both sides of the house are wonderful. We played tennis on the court with such an outstanding view. The pool looks great too, but it was out of season for us. Well located to visiting various hill top towns. We also did a wine tour at one of the many wineries in the area...
House with swimming pool. Medieval village in the heart of Chianti Classico
Aerial view
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany
10.0 out of 10, Exceptional, (5)
"We booked our stay at Villa Petrolo to host 20 guests (and one toddler) for a wedding/elopement. Our stay was fantastic from start to finish. The villa itself is beautifully decorated and looks even better in person. Each room has its own personality and there is plenty of space for everyone to enjoy time as a group or alone. The grounds are peaceful, picturesque and well taken care of. Thank you to Marco who was responsive, answered all of our questions and was extremely helpful with booking...
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany
TV, fireplace, books
Wonderful Tuscan farmhouse with large spaces and panoramic views
10.0 out of 10, Exceptional, (9)
"Everything was exactly as advertised at this beautiful Impruneta Tuscan farmhouse - perfect spot for two couples to explore Tuscany. Mattia had some excellent recommendations for areas to explore. We had beautiful views of the Tuscan hills. While we had some rainy days, that also meant we had incredible, vibrant, double rainbows appear. Accomodations: The farmhouse is just charming. There is one Jack and Jill bathroom and it has great use of small space with beautiful tile. WiFi worked fine...
Wonderful Tuscan farmhouse with large spaces and panoramic views
Outdoor dining
Holiday Home 'Casa Ernesto - Porzione Di Colonica' with Private Garden and Wi-Fi
10.0 out of 10, Exceptional, (1)
The price is NZ$321
per night
19 May - 20 May
Holiday Home 'Casa Ernesto - Porzione Di Colonica' with Private Garden and Wi-Fi
Outdoor pool
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
10.0 out of 10, Exceptional, (46)
"Large three-bedroom, three-bathroom apartment with a nice layout. The description on VRBO does not make it clear that you are only getting an apartment in a building that includes two other apartments. I thought I was booking a house. We stayed four days when the weather was not that cold, but we needed the heating, for which there is a separate charge. For four days, we spent another 100 euros. The apartment was clean and the linens and towels were of good quality. The appliances, pots and...
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Exterior
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (125)
"This charming farmhouse made our stay in the Tuscan region perfect. While we never met the host, they were very easy to communicate with and responded quickly. The farm and area is beautiful! We rented a car and did day trips to Montepulciano, Siena, Volterra, Lucca and Cinque Terre. The house is also convenient to the local town. We found excellent restaurants and also bought groceries at the Coop. Would highly recommend staying here if planning a trip to this region of Italy."
Farmhouse in the heart of the real chiantishire
Pool
Apartment House with garden Tuscany Chianti , Florence 15km.
9.8 out of 10, Exceptional, (69)
"If you are looking for a quiet getaway with an amazing view, and great restaurants around- Book this property! The host is absolutely amazing and extremely sweet and was able to accommodate our every need. The landscape was serene, and the home was perfect for our party of three with bedrooms on opposite ends for privacy."
Apartment House with garden Tuscany Chianti , Florence 15km.
Outdoor pool
Apartment in CountryHouse Cerchiaia for your holidays very close to Florence
9.8 out of 10, Exceptional, (44)
"Lovely countryside farmhouse offered us a place to relax in the evenings after full days of exploring Florence and many nearby cities. The place is well kept and comfortable, the pool is awesome. Communication with owner was responsive and prompt."
Apartment in CountryHouse Cerchiaia for your holidays very close to Florence
Property grounds
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
9.8 out of 10, Exceptional, (44)
"Clean property and helpful friendly host. Would stay here again."
CASA SOLEALTO - Cozy apartment in the countryside near Florence Arezzo and Siena
Pool
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
9.8 out of 10, Exceptional, (77)
"Sonia was the perfect host and her place was unbelievable! The view is gorgeous, the place was spacious and clean, all the little extras made it a wonderful stay for my family. My girls were sad to miss trick or treating on Halloween night and when we came back from dinner Sonia had a sweet surprise waiting for them on the door. It’s something my girls will remember forever. When we come back through Italy we will only stay with Sonia!"
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Outdoor dining
House in the heart of Chianti
9.8 out of 10, Exceptional, (15)
"A rustic Tuscan converted barn with a stunning location and views to die for. 10-minute walk (uphill) to the village for excellent restaurant options and supplies. Manu was a wonderful and accommodating host, offering a warm welcome and lots of assistance with local bookings and recommendations. BBQ dinners by the pool at dusk were a highlight!"
House in the heart of Chianti
Exterior
Torrino: Panoramic house in Chianti, 20 minutes from Siena, Florence and San Gimignano
9.8 out of 10, Exceptional, (41)
"This was a beautiful home in an enchanting medieval town! It was a good location to explore Florence, Siena and the surrounding areas. The view over the valley was wonderful!"
Torrino: Panoramic house in Chianti, 20 minutes from Siena, Florence and San Gimignano
Property grounds
CASALINI 1 - Farmhouse in Chianti - Free wi fi, swimming pool
9.6 out of 10, Exceptional, (14)
"Wish we had more time to relax here, beautiful home- thank you for sharing it with us."
CASALINI 1 - Farmhouse in Chianti - Free wi fi, swimming pool
Property grounds
House with character in typical medieval borgo on the Chianti Classico hills
9.6 out of 10, Exceptional, (44)
"A very beautiful property and grounds, in the middle of the Tuscan countryside The patio area with charcoal grill amongst the olive trees was a beautiful setting for snacks and meals The house inside was very rustic and authentic but comfortable and the kitchen and bathroom s are well equipped Our hosts were very friendly and the welcome bottle of wine and fresh fruit basket was a wonderful touch after a long day of travelling The neighbours were lovely we spoke to several of them though a...
House with character in typical medieval borgo on the Chianti Classico hills
Pool
House in a typical village in the heart of Chianti
9.6 out of 10, Exceptional, (58)
"Our stay in this enchanting little village was just perfection. Our renovated “barn” was so cozy and comfortable, Our host, Veronica could not have been more attentive to our needs (it was quite cold when we were there and she made sure we had fuel, etc to stay warm). She also brought us wine and olive oil from her family and a delicious tart. It was peaceful, beautiful and everything we could have hoped for. Thank you Veronica and Massimiliano for sharing your magical little corner of Italy!...
House in a typical village in the heart of Chianti
Pool
House in a typical village in the heart of Chianti
9.6 out of 10, Exceptional, (24)
"A lovely location and friendly hosts who were willing to make the extra effort. It is a small property but with everything you need. It is not the property in the photographs but close to that property. It is a holiday complex with mainly non Italian guests but authentic Castellina in Chianti is a 15 min drive away."
House in a typical village in the heart of Chianti
Property grounds
Villa with large garden in the Chianti hills
9.4 out of 10, Exceptional, (62)
"Had a great stay here and met the lovely Ben and his beautiful garden :) plus the 4 local cats hanging around :) great base for us to drive and explore the area :) would definitely stay again at this property."
Villa with large garden in the Chianti hills
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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.

Other property types in Chianti Region

Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (49)
"We cannot recommend this villa highly enough!! There are no words to fully describe the beauty of Isola Serena. The main villa & new guesthouses, along with the outdoor spaces, were so thoughtfully and beautifully restored - the property was both luxurious and authentic to Tuscan style. It was easily the most beautiful place we have ever had the opportunity to stay, with views that almost seemed like they couldn't be real! The hosts, Serena and Peter, were so kind and communicative before &...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Pool
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
9.4 out of 10, Exceptional, (54)
"This is a great place to stay with multiple families. You are all together but have your own separate space and kitchen. We stayed here with family and attended our sons wedding nearby!! There is a great restaurant that we drove to not far from the Villa that I highly recommend: Osteria Del Tempo Perso - Montespertoli FI There is a Coop about 15 min drive and 25 min to downtown Florence"
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Exterior
Hu Norcenni Girasole Village
4.0 star property
8.4 out of 10, Very good, (237)
"The location is really beautiful. There are constant shuttles to transport from one location to other within the property. Nice food options and music on specific days Clean Cabins If you have not booked shuttle from the Figline station to this place- you may have a hard time getting a taxi from the station. I recommend to plan ahead for the commute from the train station to this property."
The price is NZ$80
per night
15 May - 16 May
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.

Chianti Region Holiday Homes information

Number of reviews
660
Accommodation
379 Holiday Homes
Lowest Price
Highest Price

Recent Reviews in Chianti Region
Expedia verified reviews

Hotel Villa Cesi

Hotel Villa Cesi

5/5 Excellent
Wish we could stay longer
"A wonderful 2 night stay in Tuscany. This hotel is absolutely fabulous. Calm and relaxing place. The staff are so thoughtful and caring. The Manager / Owner should be so proud of all of them. Amazing"
A verified traveller stayed at Hotel Villa Cesi
Posted 3 days ago
Hotel Villa Cesi