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 121 to 150 of 169 villas
min $1,030/wkmax $1,373/wk- min $927/wk
- max $1,236/wk
- Min Stay: 7 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 2 bathrooms
Swimming Pool
Washing Machine
Maid Service
** Save up to $137 when you book by Feb-28-2021**
min $9,100/wkmax $15,680/wk- min $8,190/wk
- max $14,112/wk
- Min Stay: 7 days
Sleeps 29 people
- 5 single bedrooms
- 12 double bedrooms
- 16 bathrooms
Independent House- Swimming Pool
Air Conditioning
** Save up to $1,568 when you book by Feb-28-2021**
min $1,939/wkmax $2,370/wk- min $1,745/wk
- max $2,133/wk
- Min Stay: 4 days
Sleeps 6 to 7 people
- 3 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $237 when you book by Feb-28-2021**
"
Fantastic, better than our high expectations!..." - Harri
min $2,451/wkmax $3,823/wk- min $2,206/wk
- max $3,441/wk
- Min Stay: 7 days
Sleeps 8 to 10 people
- 4 double bedrooms
- 3 bathrooms
- Swimming Pool
** Save up to $382 when you book by Feb-28-2021**
min $709/wkmax $1,752/wk- min $638/wk
- max $1,577/wk
- Min Stay: 3 days
Sleeps 3 people
- Studio and/or Loft
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $175 when you book by Feb-28-2021**
"
Excellent value for the price!..." - Rosemary
min $834/wkmax $1,079/wk- min $751/wk
- max $971/wk
- Min Stay: 7 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
** Save up to $108 when you book by Feb-28-2021**
min $5,488/wkmax $7,840/wk- min $4,939/wk
- max $7,056/wk
- Min Stay: 7 days
Sleeps 6 people
- 3 double bedrooms
- 3 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $784 when you book by Feb-28-2021**
min $11,669/wkmax $20,419/wk- min $10,502/wk
- max $18,377/wk
- Min Stay: 7 days
Sleeps 20 people
- 10 double bedrooms
- 11 bathrooms
- Independent House
- Swimming Pool
- Air Conditioning
** Save up to $2,042 when you book by Feb-28-2021**
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 Feb-28-2021**
min $13,797/wkmax $23,002/wk- min $12,417/wk
- max $20,702/wk
- Min Stay: 7 days
Sleeps 8 people
- 4 double bedrooms
- 3 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $2,300 when you book by Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
min $9,478/wkmax $16,772/wk- min $8,530/wk
- max $15,095/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 5 bathrooms
- Independent House
- Washing Machine
- Air Conditioning
** Save up to $1,677 when you book by Feb-28-2021**
$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 Feb-28-2021**
min $1,471/wkmax $2,059/wk- min $1,324/wk
- max $1,853/wk
- Min Stay: 7 days
Sleeps 4 to 7 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $206 when you book by Feb-28-2021**
min $1,226/wkmax $1,667/wk- min $1,103/wk
- max $1,500/wk
- Min Stay: 7 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $167 when you book by Feb-28-2021**
"
Pure heaven! The place was beautifully restored and decorated, the setting was perfect, the staff were incredibly helpful and nice. We couldn't have asked for..." - Dana
min $834/wkmax $1,079/wk- min $751/wk
- max $971/wk
- Min Stay: 7 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
** Save up to $108 when you book by Feb-28-2021**
"
Very unique and attractive...." - Jorge
min $834/wkmax $1,079/wk- min $751/wk
- max $971/wk
- Min Stay: 7 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
** Save up to $108 when you book by Feb-28-2021**
"
An experience of a lifetime! Fantastic from any angle or view!
..." - Karen
min $1,226/wkmax $1,667/wk- min $1,103/wk
- max $1,500/wk
- Min Stay: 7 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
** Save up to $167 when you book by Feb-28-2021**
"
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
Displaying 121 to 150 of 169 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..