Search Vacation Homes in Chianti Region

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Compare 382 Vacation Homes in Chianti Region with updated reviews, rates, and availability.

Pool
detached villa with private pool and garden
9.0 out of 10, Wonderful, (14)
"Superb private villa with enclosed pool & garden only 5 mins walk from the town. Federico is a friendly & helpful host. We were even given fresh eggs by his Dad! Views from the garden are lovely. We had a great stay - thank you. If you are taking a dog just check the costs - we paid £50 when we booked and were charged a further €70 when we left."
detached villa with private pool and garden
Holiday Home Exterior [summer]
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
Property grounds
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
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Golf, Outdoor, Pool, Summer
Stunning villa for 6 guests with A/C, WIFI, private pool, TV, patio and parking
10.0 out of 10, Exceptional, (1)
Stunning villa for 6 guests with A/C, WIFI, private pool, TV, patio and parking
Outdoor dining
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
9.8 out of 10, Exceptional, (61)
"This villa was perfect for our stay. It is beautiful, super comfortable (we had 9 adults) and private yet only 10 min drive to a grocery store and cute restaurants. And a great location for day trips to Siena and local wineries. The hosts were easy to communicate with, and we loved our in home dinner prepared by Simona. I cannot recommend this place enough."
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
Property grounds
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
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
Pool
House with swimming pool. Medieval village in the heart of Chianti Classico
10.0 out of 10, Exceptional, (102)
"We had wonderful stay at Localita Granaio and in the Castellini in Chianti area. The villa was amazing with its history and setting and we loved the beautiful views as we sat on the patio with our wine and cheese. Our host Pietro could not have been better- helpful but not intrusive, informative and friendly. The general area also had so much to offer. We would go back in a minute! Thanks Pietro"
House with swimming pool. Medieval village in the heart of Chianti Classico
Pool
In the hearth of Chianti, lovely country house
10.0 out of 10, Exceptional, (64)
"Casa splendida, molto più bella di come appare nelle foto, arredata con grande gusto per i dettagli, dotata di tutto, circondata da colline e cipressi, con una veranda all'aperto dove mangiare, rilassarsi e stare insieme ed una piscina non grande ma circondata dal verde e piacevolissima."
In the hearth of Chianti, lovely country house
Exterior
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
Villa Petrolo garden overview
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
Property grounds
Info House
9.8 out of 10, Exceptional, (6)
"Giovanni was an amazing host. He even gave us a welcoming gift of a bottle of wine and apples. I had such an incredible time just relaxing in the peace and quiet and getting some writing done. I would recommend this spot to anyone who is interested in doing the same."
Info House
Living 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.
Outdoor dining
Casa Elena-panoramic Chianti Hills
9.0 out of 10, Wonderful, (2)
"It is in beautiful location where you can recieve the healing energy of the Toscana countryside. However it's far from Florence, 45 minutes through a long and widing road. Internet and telephone signal is bad and we did't get the code to open the box with the keys on time, we strugeled to find a way to communicate with the staff. Should we have received the code in time everything would have been perfect. It would be a good idea to place the name of the house "Elena" somewhere visible for people...
Casa Elena-panoramic Chianti Hills
Children's area
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
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
The main pool with solar heating, tennis court and outside dining area
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
10.0 out of 10, Exceptional, (16)
"This was an excellent rental and one of our best stays ever of the 30 years we have been coming to Castellina. The house was typically rustic Tuscan but very well supplied with everything we might need, including good Internet access, excellent bathrooms, an impressive separate sitting room with our own patio and small garden with the most exceptional views over the surrounding Tuscan countryside we quite possibly have ever seen. There were communal gardens and huge, modern pool, both...
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Pool
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
CASALINI 1 - Farmhouse in Chianti - Free wi fi, swimming pool
9.6 out of 10, Exceptional, (14)
"Great house in Chianti region on a vineyard about 30 minutes from Florence. Off the beaten track so a vehicle is a necessity. The location made it easy to take day trips to Vinci and San Gimignano. Took the T1 tram into downtown Florence for sightseeing."
CASALINI 1 - Farmhouse in Chianti - Free wi fi, swimming pool
Private Garden
Casa Elena-Panoramic Chianti Hills, Greve in Chianti, Italy
Casa Elena-Panoramic Chianti Hills, Greve in Chianti, Italy
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See all available properties in Chianti Region
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
Hu Norcenni Girasole Village
4.0 star property
8.4 out of 10, Very Good, (242)
"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 SAR 207
SAR 235 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Hu Norcenni Girasole Village
Front of property
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, (24)
"The staff is friendly and helpful. This is a nice place to stay . "
The price is SAR 295
SAR 328 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Camping Village Il Poggetto
Exterior
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
9.4 out of 10, Exceptional, (56)
"The villa was a combination of multiple separate apartments, which allowed for plenty of comfort and privacy for our big group. The main floor apartment had a dining table and living space that could fit all of us when we wanted to gather. We took advantage of the pool (a bit of a cold plunge, since we were there in the spring weather), and admired the lovely views of the countryside from the outdoor areas. The location is very easy to get to from Florence. Our group went to Siena as a day trip...
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
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.

Recent reviews of Chianti Region hotels
Expedia verified reviews

Relais Vignale & Spa

Relais Vignale & Spa

5/5 Excellent
"Beautiful room, great view. Good breakfast, enjoyed the restaurant for dinner. Property was well maintained. Lots of wonderful places to sit and relax with a book and/or a drink. "
A verified traveler stayed at Relais Vignale & Spa
Posted 8 days ago
Relais Vignale & Spa