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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 151 to 180 of 168 villas
Save $546 Photo of Charming Tuscan Villa on Large Estate
  • min $2,940/wk
  • max $5,460/wk
  • min $2,646/wk
  • max $4,914/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $546 when you book by Jan-31-2021**
" Excellent...." - Colin
Save $254 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,345/wk
  • max $2,539/wk
  • min $1,211/wk
  • max $2,285/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $254 when you book by Jan-31-2021**
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,617/wk
  • max $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**
Save $467 Photo of Villa Rental in Tuscany, San Casciano in Val di Pesa (Chianti Area)
  • min $1,226/wk
  • max $1,667/wk
  • min $883/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $467 when you book by Jan-31-2021**
" Wonderful, bucolic setting --just what we needed to relax and get away from it all...." - Barbara
Save $577 Photo of Apartment Rental in Tuscany, San Casciano in Val di Pesa (Chianti Area)
  • min $1,471/wk
  • max $2,059/wk
  • min $1,059/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $577 when you book by Jan-31-2021**
" Our experience was amazing!!! Property is pristine in the middle of the country with beautiful walking paths and roads around. ..." - Kamellia
Save $577 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,059/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $577 when you book by Jan-31-2021**
" This was the most wonderful experience I have ever had. Think of the movie Under the Tuscan Sun... well, this villa is exactly that on steroids! So romantic, staf..." - Jackie
Save $577 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,059/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $577 when you book by Jan-31-2021**
" My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
Save $146 Photo of Charming 14th Century Apartment in the Center of a Medieval Town in Tuscany
  • $1,458/wk
  • $1,312/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $146 when you book by Jan-31-2021**
" The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
Save $1,470 Photo of Rural Woodland Tuscan villa with Pool and BBQ near Montaione
  • $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 Jan-31-2021**
Save $1,470 Photo of Villa Rental in Tuscany, Rignano sull'Arno
  • min $10,290/wk
  • max $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 Jan-31-2021**
Save $1,200 Photo of House Rental in Tuscany, Barberino Val d'Elsa (Chianti Area)
  • min $7,203/wk
  • max $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 Jan-31-2021**
Save $2,560 Photo of Villa Rental in Tuscany, Greve (Chianti Area)
  • min $20,796/wk
  • max $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 Jan-31-2021**
Save $1,960 Photo of Villa Rental in Tuscany, Figline Valdarno (Chianti Area)
  • min $13,720/wk
  • max $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 Jan-31-2021**
Save $2,666 Photo of Villa Rental in Tuscany, Figline Valdarno (Chianti Area)
  • min $18,620/wk
  • max $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 Jan-31-2021**
Save $304 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,961/wk
  • max $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 Jan-31-2021**
Save $255 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $1,765/wk
  • max $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 Jan-31-2021**
Save $2,310 Photo of Villa Rental in Tuscany, Castelfalfi
  • min $14,630/wk
  • max $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 Jan-31-2021**
  • min $9,478/wk
  • max $16,772/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Washing Machine
  • Air Conditioning
 
Displaying 151 to 180 of 168 villas

Show all 209 Villas and Houses for Rent in Florence

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..