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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.   Continue >

Displaying 61 to 90 of 182 villas
Save $1,532 Photo of Private Villa on a Castle Estate near Certaldo
  • min $11,727/wk
  • max $15,316/wk
  • min $10,554/wk
  • max $13,784/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,532 when you book by Mar-31-2019**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $138 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $899/wk
  • max $1,381/wk
  • min $809/wk
  • max $1,243/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $138 when you book by Mar-31-2019**
Save $145 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,088/wk
  • max $1,451/wk
  • min $979/wk
  • max $1,306/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $145 when you book by Mar-31-2019**
" It was the most wonderful place. So very near Firenze and yet in the quiet and lovely countryside. The administrator was very helpful and charming. We enjoy every ..." - Susana
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,451/wk
  • max $1,960/wk
  • min $1,306/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $196 when you book by Mar-31-2019**
Save $125 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,245/wk
  • min $838/wk
  • max $1,121/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $125 when you book by Mar-31-2019**
Save $125 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,245/wk
  • min $838/wk
  • max $1,121/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $125 when you book by Mar-31-2019**
Save $482 Photo of Charming Apartments in Tuscany Perfect for a Family Holiday
  • min $3,852/wk
  • max $4,816/wk
  • min $3,467/wk
  • max $4,334/wk
  • Min Stay: 7 days
Sleeps 5 to 8 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $482 when you book by Mar-31-2019**
Save $226 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $1,790/wk
  • max $2,257/wk
  • min $1,611/wk
  • max $2,031/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $226 when you book by Mar-31-2019**
" Fabulous...." - Jane
Save $313 Photo of Tuscan Villa with a Private Pool in a Village
  • min $701/wk
  • max $3,127/wk
  • min $631/wk
  • max $2,814/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $313 when you book by Mar-31-2019**
" We stayed there for a summer in 2009 it was a wonderful experience then and again this visit. We know the rhythm of the village so enjoy all it has to offer..." - Joy
Save $2,366 Photo of Large Luxury Villa Rental in the Chianti with Spectacular Views
  • min $12,182/wk
  • max $23,663/wk
  • min $10,964/wk
  • max $21,297/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,366 when you book by Mar-31-2019**
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
Save $2,275 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • min $4,901/wk
  • max $9,708/wk
  • min $3,308/wk
  • max $8,737/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,275 when you book by Mar-31-2019**
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
Save $448 Photo of Lovely Tuscan Villa with Swimming Pool and Views
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Mar-31-2019**
" Outstanding! The villa was even better than it looked in the pictures on the website. Check in was very easy and staff were very helpful in answering any questions..." - Julie
Save $560 Photo of Tuscany Villa Rental near Greve
  • min $2,941/wk
  • max $5,601/wk
  • min $2,647/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Mar-31-2019**
" Excellent. ..." - Thomas
Save $1,092 Photo of Traditional Tuscan Villa on a Large Estate
  • min $6,930/wk
  • max $10,920/wk
  • min $6,237/wk
  • max $9,828/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,092 when you book by Mar-31-2019**
" Wonderful!..." - Chuck
Save $308 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,625/wk
  • max $3,081/wk
  • min $1,463/wk
  • max $2,773/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $308 when you book by Mar-31-2019**
" Excellent. Beautiful house and property...." - Gary
Save $493 Photo of Tuscan Farmhouse Rental on Large Estate
  • min $4,541/wk
  • max $4,928/wk
  • min $4,087/wk
  • max $4,435/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $493 when you book by Mar-31-2019**
Save $448 Photo of Tuscan Villa with Gardens and Pool for a Family
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Mar-31-2019**
" The setting is very quaint. ..." - Mike
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,617/wk
  • min $662/wk
  • max $1,455/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 $162 when you book by Mar-31-2019**
" 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
Save $1,160 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,616/wk
  • max $11,603/wk
  • min $6,854/wk
  • max $10,443/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,160 when you book by Mar-31-2019**
" Amazing. We has a wonderful time. ..." - Tim
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,107/wk
  • min $1,447/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $211 when you book by Mar-31-2019**
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,107/wk
  • min $1,447/wk
  • max $1,896/wk
  • Min Stay: 3 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 Mar-31-2019**
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,107/wk
  • min $1,447/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Mar-31-2019**
" Luigi and his staff were great. Friendly and responsive...." - John
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,617/wk
  • min $794/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Mar-31-2019**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $1,568/wk
  • min $880/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Mar-31-2019**
" 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
Save $168 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,676/wk
  • min $662/wk
  • max $1,508/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $168 when you book by Mar-31-2019**
" 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
Save $2,528 Photo of Ancient Hamlet in Tuscany near Florence
  • min $18,944/wk
  • max $25,284/wk
  • min $17,050/wk
  • max $22,756/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,528 when you book by Mar-31-2019**
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $653/wk
  • max $1,326/wk
  • min $588/wk
  • max $1,193/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 Mar-31-2019**
Save $179 Photo of Tuscan Apartment in Historic Castle
  • min $916/wk
  • max $1,790/wk
  • min $824/wk
  • max $1,611/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $179 when you book by Mar-31-2019**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $119 Photo of Tuscan Apartment in Historic Castle
  • min $727/wk
  • max $1,192/wk
  • min $654/wk
  • max $1,073/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $119 when you book by Mar-31-2019**
" Ambiance. Staff was very good...." - Will
Save $191 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,911/wk
  • min $794/wk
  • max $1,720/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $191 when you book by Mar-31-2019**
" It was comfortable, clean, and conveniently located. ..." - Misty
 
Displaying 61 to 90 of 182 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..