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 168 villas
min $490/wkmax $1,081/wk- min $441/wk
- max $973/wk
- Min Stay: 3 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
Swimming Pool
Washing Machine
Maid Service
** Save up to $108 when you book by Jan-31-2021**
min $770/wkmax $1,853/wk- min $693/wk
- max $1,668/wk
- Min Stay: 3 days
Sleeps 5 people
- 1 single bedrooms
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $185 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 6 people
- 2 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $154 when you book by Jan-31-2021**
"
Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
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 Jan-31-2021**
"
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 $700/wkmax $1,699/wk- min $630/wk
- max $1,529/wk
- Min Stay: 3 days
Sleeps 4 to 5 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $170 when you book by Jan-31-2021**
"
Wonderful. A magnificent castle with out-buildings in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 ..." - Michael
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 Jan-31-2021**
"
Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
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 Jan-31-2021**
"
Love this property. Second year in a row I have been there...." - Sadia
min $700/wkmax $1,760/wk- min $630/wk
- max $1,584/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $176 when you book by Jan-31-2021**
"
We thoroughly enjoyed our stay and the property was very well-maintained. We would recommend staying here to others. We quickly realized, however, that some of the..." - Wendy
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 Jan-31-2021**
"
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 Jan-31-2021**
"
Ambiance.
Staff was very good...." - Will
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 Jan-31-2021**
min $6,721/wkmax $9,708/wk- min $6,049/wk
- max $8,737/wk
- Min Stay: 5 days
Sleeps 20 people
- 2 single bedrooms
- 9 double bedrooms
- 11 bathrooms
Independent House- Swimming Pool
- Washing Machine
** Save up to $971 when you book by Jan-31-2021**
"
A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
min $700/wkmax $1,545/wk- min $630/wk
- max $1,391/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $155 when you book by Jan-31-2021**
"
We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
min $770/wkmax $1,699/wk- min $693/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 Jan-31-2021**
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 Jan-31-2021**
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 Jan-31-2021**
min $534/wkmax $1,235/wk- min $481/wk
- max $1,112/wk
- Min Stay: 3 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $124 when you book by Jan-31-2021**
min $700/wkmax $1,392/wk- min $630/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 had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
min $1,512/wkmax $2,205/wk- min $1,361/wk
- max $1,985/wk
- Min Stay: 7 days
Sleeps 6 to 7 people
- 3 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
** Save up to $221 when you book by Jan-31-2021**
"
We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
min $1,078/wkmax $3,065/wk- min $970/wk
- max $2,759/wk
- Min Stay: 7 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
Air Conditioning
** Save up to $307 when you book by Jan-31-2021**
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 Jan-31-2021**
min $709/wkmax $1,752/wk- min $638/wk
- max $1,577/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $175 when you book by Jan-31-2021**
min $1,960/wkmax $4,322/wk- min $1,764/wk
- max $3,890/wk
- Min Stay: 3 days
Sleeps 8 to 9 people
- 4 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $432 when you book by Jan-31-2021**
"
We had a very pleasant stay and would recommend the property...." - Amy
min $10,469/wkmax $11,202/wk- min $9,422/wk
- max $10,082/wk
- Min Stay: 4 days
Sleeps 24 to 28 people
- 12 double bedrooms
- 13 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $1,120 when you book by Jan-31-2021**
"
Overall, it was positive...." - Cheryl
Displaying 61 to 90 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..