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 31 to 60 of 168 villas
min $772/wkmax $1,392/wk- min $695/wk
- max $1,253/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
Swimming Pool
Washing Machine
Maid Service
** Save up to $139 when you book by Jan-31-2021**
"
We loved everything about it, the architecture is wonderful, the grounds are like heaven. I would like to think the people-staff are the best, and we are going ba..." - Barbara
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 Jan-31-2021**
min $928/wkmax $1,647/wk- min $835/wk
- max $1,482/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $165 when you book by Jan-31-2021**
"
Driving up to the Castle was a surreal experience. It looks like a castle from a story book. The frescoes were everywhere, including the entire room. It made fo..." - Lauren
min $1,078/wkmax $1,421/wk- min $970/wk
- max $1,279/wk
- Min Stay: 7 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
Air Conditioning
** Save up to $142 when you book by Jan-31-2021**
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 Jan-31-2021**
min $771/wkmax $1,541/wk- min $694/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 Jan-31-2021**
"
Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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 Jan-31-2021**
min $858/wkmax $1,449/wk- min $772/wk
- max $1,304/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $145 when you book by Jan-31-2021**
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 Jan-31-2021**
"
It was comfortable, clean, and conveniently located. ..." - Misty
min $1,050/wkmax $2,239/wk- min $945/wk
- max $2,015/wk
- Min Stay: 3 days
Sleeps 8 people
- 4 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $224 when you book by Jan-31-2021**
"
We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
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 Jan-31-2021**
"
We'll be back...." - Tammy
min $700/wkmax $1,699/wk- min $630/wk
- max $1,529/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 single bedrooms
- 1 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $170 when you book by Jan-31-2021**
"
Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
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 Jan-31-2021**
"
Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
min $700/wkmax $1,622/wk- min $630/wk
- max $1,460/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 Jan-31-2021**
min $630/wkmax $1,315/wk- min $567/wk
- max $1,184/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
Independent House- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $132 when you book by Jan-31-2021**
min $622/wkmax $1,392/wk- min $560/wk
- max $1,253/wk
- Min Stay: 3 days
Sleeps 2 to 3 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $139 when you book by Jan-31-2021**
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 Jan-31-2021**
"
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 $840/wkmax $1,825/wk- min $756/wk
- max $1,643/wk
- Min Stay: 3 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $183 when you book by Jan-31-2021**
"
We absolutely loved our time at Il Castello 27! Our family loved the property and the people that worked there were so friendly and helpful!..." - Sharon
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 $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 Jan-31-2021**
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 Jan-31-2021**
Displaying 31 to 60 of 168 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..