Vacation Accommodation Chianti Tuscany Villa Rentals
South of Florence lies the Chianti, Italy's definitive wine-growing region. This area boasts hills covered in vineyards, winding roads (favored by sporty drivers and daredevil cyclists), and breathtaking vistas.
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Displaying 1 to 30 of 171 villas
Save $413
- min $1,680/wk
- max $2,450/wk
- Min Stay: 7 days
Sleeps 6 to 7 people
- 3 double bedrooms
- 3 bathrooms
Swimming Pool
Washing Machine
"
We loved everything about our stay. Three couples stayed in Poggio 2. We were very comfortable--the 3 bedroom, 3 bath apartment was perfect. It was quiet and p..." - Mary
- min $834/wk
- max $1,079/wk
- Min Stay: 7 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
Maid Service
"
An experience of a lifetime! Fantastic from any angle or view!
..." - Karen
Save $1,162
- min $1,357/wk
- max $2,017/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
- min $834/wk
- max $1,079/wk
- Min Stay: 7 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
"
Very unique and attractive...." - Jorge
- min $1,190/wk
- max $1,890/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- min $1,471/wk
- max $2,059/wk
- Min Stay: 7 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
"
Our experience was amazing!!! Property is pristine in the middle of the country with beautiful walking paths and roads around. ..." - Kamellia
- min $23,519/wk
- max $44,865/wk
- Min Stay: 7 days
Sleeps 80 to 120 people
- 1 single bedrooms
- 42 double bedrooms
- 35 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
- min $1,471/wk
- max $2,059/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Maid Service
"
My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
- min $4,480/wk
- max $6,335/wk
- Min Stay: 7 days
Sleeps 12 to 15 people
- 6 double bedrooms
- 6 bathrooms
Independent House- Swimming Pool
- Washing Machine
- min $1,226/wk
- max $1,667/wk
- Min Stay: 7 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
"
It was SO beautiful and enchanting staying up in the Tuscan hills in a 9th century castle. Everyone was so friendly and helpful and the views from our windows wer..." - Linda
- min $700/wk
- max $1,470/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
Displaying 1 to 30 of 171 villas
Following the old Chiantigiana road you see the heart of this region, including the northerly reaches of San Casciano and its environs and the Chianti Classico. What to do while in the Chianti? Eat, drink, and be merry. Towns like Panzano, Greve-in-Chianti, and Radda-in-Chianti---and all the wineries in between---are filled with gastronomic delights and a dizzying selection of wine shops. A wonderful place to bring your family or friends for an unforgettable Tuscan experience. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..