South Florence Villas and Vacation 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 151 to 180 of 168 villas
min $1,345/wkmax $2,539/wk- min $1,211/wk
- max $2,285/wk
- Min Stay: 7 days
Sleeps 6 people
- 3 double bedrooms
- 2 bathrooms
Swimming Pool
Washing Machine
Maid Service
** Save up to $254 when you book by Jan-31-2021**
"
It is a beautiful setting for a relaxed vacation...." - ANNAMMA
min $1,617/wkmax $2,107/wk- min $1,455/wk
- max $1,896/wk
- Min Stay: 7 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
Air Conditioning
** Save up to $211 when you book by Jan-31-2021**
min $1,226/wkmax $1,667/wk- min $883/wk
- max $1,500/wk
- Min Stay: 7 days
Sleeps 3 people
- 1 single bedrooms
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $467 when you book by Jan-31-2021**
"
Wonderful, bucolic setting --just what we needed to relax and get away from it all...." - Barbara
min $1,471/wkmax $2,059/wk- min $1,059/wk
- max $1,853/wk
- Min Stay: 7 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
** Save up to $577 when you book by Jan-31-2021**
"
Our experience was amazing!!! Property is pristine in the middle of the country with beautiful walking paths and roads around. ..." - Kamellia
min $1,471/wkmax $2,059/wk- min $1,059/wk
- max $1,853/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Maid Service
** Save up to $577 when you book by Jan-31-2021**
"
This was the most wonderful experience I have ever had. Think of the movie Under the Tuscan Sun... well, this villa is exactly that on steroids!
So romantic, staf..." - Jackie
min $1,471/wkmax $2,059/wk- min $1,059/wk
- max $1,853/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Maid Service
** Save up to $577 when you book by Jan-31-2021**
"
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
$1,458/wk- $1,312/wk
- Min Stay: 7 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 2 bathrooms
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $146 when you book by Jan-31-2021**
"
The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
$14,702/wk- $13,232/wk
- Min Stay: 7 days
Sleeps 16 people
- 8 double bedrooms
- 9 bathrooms
Independent House- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,470 when you book by Jan-31-2021**
min $10,290/wkmax $14,700/wk- min $9,261/wk
- max $13,230/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 6 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,470 when you book by Jan-31-2021**
min $7,203/wkmax $11,998/wk- min $6,483/wk
- max $10,798/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 6 bathrooms
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,200 when you book by Jan-31-2021**
min $20,796/wkmax $25,599/wk- min $18,716/wk
- max $23,039/wk
- Min Stay: 7 days
Sleeps 16 people
- 8 double bedrooms
- 8 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $2,560 when you book by Jan-31-2021**
min $13,720/wkmax $19,600/wk- min $12,348/wk
- max $17,640/wk
- Min Stay: 7 days
Sleeps 14 people
- 7 double bedrooms
- 7 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,960 when you book by Jan-31-2021**
min $18,620/wkmax $26,656/wk- min $16,758/wk
- max $23,990/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 6 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $2,666 when you book by Jan-31-2021**
min $1,961/wkmax $3,039/wk- min $1,765/wk
- max $2,735/wk
- Min Stay: 7 days
Sleeps 6 to 8 people
- 3 double bedrooms
- 2 bathrooms
- Swimming Pool
** Save up to $304 when you book by Jan-31-2021**
min $1,765/wkmax $2,549/wk- min $1,589/wk
- max $2,294/wk
- Min Stay: 7 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
** Save up to $255 when you book by Jan-31-2021**
min $14,630/wkmax $23,100/wk- min $13,167/wk
- max $20,790/wk
- Min Stay: 7 days
Sleeps 10 people
- 5 double bedrooms
- 5 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $2,310 when you book by Jan-31-2021**
- min $9,478/wk
- max $16,772/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 5 bathrooms
- Independent House
- Washing Machine
- Air Conditioning
Displaying 151 to 180 of 168 villas
Show all 209 Villas and Houses for Rent in Florence
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..