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 61 to 90 of 165 villas
min $1,071/wkmax $1,701/wk- min $964/wk
- max $1,531/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
Swimming Pool
Washing Machine
** Save up to $170 when you book by Apr-30-2021**
min $700/wkmax $1,624/wk- min $630/wk
- max $1,462/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
Maid Service
** Save up to $162 when you book by Apr-30-2021**
"
We'll be back...." - Tammy
min $534/wkmax $1,235/wk- min $481/wk
- max $1,112/wk
- Min Stay: 3 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $124 when you book by Apr-30-2021**
"
Love this property. Second year in a row I have been there...." - Sadia
min $613/wkmax $1,328/wk- min $552/wk
- max $1,195/wk
- Min Stay: 3 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $133 when you book by Apr-30-2021**
"
The castle is beautiful...." - Serena
min $692/wkmax $1,252/wk- min $623/wk
- max $1,127/wk
- Min Stay: 3 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $125 when you book by Apr-30-2021**
"
Ambiance.
Staff was very good...." - Will
min $841/wkmax $1,541/wk- min $757/wk
- max $1,387/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $154 when you book by Apr-30-2021**
"
Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
min $840/wkmax $2,007/wk- min $756/wk
- max $1,806/wk
- Min Stay: 3 days
Sleeps 6 people
- 3 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $201 when you book by Apr-30-2021**
"
It was comfortable, clean, and conveniently located. ..." - Misty
min $875/wkmax $1,879/wk- min $788/wk
- max $1,691/wk
- Min Stay: 3 days
Sleeps 4 to 6 people
- 3 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $188 when you book by Apr-30-2021**
"
Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
min $1,281/wkmax $2,132/wk- min $1,153/wk
- max $1,919/wk
- Min Stay: 7 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
** Save up to $213 when you book by Apr-30-2021**
min $1,313/wkmax $2,611/wk- min $1,182/wk
- max $2,350/wk
- Min Stay: 3 days
Sleeps 6 people
- 3 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $261 when you book by Apr-30-2021**
"
Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
min $709/wkmax $1,417/wk- min $638/wk
- max $1,275/wk
- Min Stay: 3 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $142 when you book by Apr-30-2021**
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
** Save up to $211 when you book by Apr-30-2021**
min $910/wkmax $1,825/wk- min $819/wk
- max $1,643/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $183 when you book by Apr-30-2021**
min $840/wkmax $1,400/wk- min $756/wk
- max $1,260/wk
- Min Stay: 7 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $140 when you book by Apr-30-2021**
"
We had a wonderful stay. The villa was just what we were looking for.
The property manager was very good and gave us great information about what to see and wher..." - Virginia
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 Apr-30-2021**
min $709/wkmax $1,647/wk- min $638/wk
- max $1,482/wk
- Min Stay: 3 days
Sleeps 3 to 4 people
- 1 single bedrooms
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $165 when you book by Apr-30-2021**
min $1,322/wkmax $2,327/wk- min $1,190/wk
- max $2,094/wk
- Min Stay: 7 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $233 when you book by Apr-30-2021**
min $1,092/wkmax $1,820/wk- min $983/wk
- max $1,638/wk
- Min Stay: 7 days
Sleeps 6 to 7 people
- 3 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $182 when you book by Apr-30-2021**
"
It is difficult to find the appropriate words to express how wonderful our experience at Casa della Fioraia was. The view we awoke to every day was spectacular. ..." - Bill
min $4,032/wkmax $5,701/wk- min $3,629/wk
- max $5,131/wk
- Min Stay: 7 days
Sleeps 12 to 15 people
- 6 double bedrooms
- 6 bathrooms
Independent House- Swimming Pool
- Washing Machine
** Save up to $570 when you book by Apr-30-2021**
min $10,381/wkmax $14,819/wk- min $9,343/wk
- max $13,337/wk
- Min Stay: 7 days
Sleeps 10 people
- 5 double bedrooms
- 3 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,482 when you book by Apr-30-2021**
min $1,015/wkmax $9,240/wk- min $914/wk
- max $8,316/wk
- Min Stay: 3 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $924 when you book by Apr-30-2021**
min $840/wkmax $1,699/wk- min $756/wk
- max $1,529/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $170 when you book by Apr-30-2021**
"
Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
min $1,147/wkmax $2,375/wk- min $1,032/wk
- max $2,138/wk
- Min Stay: 3 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $238 when you book by Apr-30-2021**
min $1,470/wkmax $1,960/wk- min $1,323/wk
- max $1,764/wk
- Min Stay: 7 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $196 when you book by Apr-30-2021**
Displaying 61 to 90 of 165 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..