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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 165 villas
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 Apr-30-2021**
" 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 $2,300 Photo of Villa Rental in Tuscany, Tavarnelle in val di Pesa
  • min $13,797/wk
  • max $23,002/wk
  • min $12,417/wk
  • max $20,702/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,300 when you book by Apr-30-2021**
Save $784 Photo of Villa Rental in Tuscany, Figline Valdarno (Chianti Area)
  • min $5,488/wk
  • max $7,840/wk
  • min $4,939/wk
  • max $7,056/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $784 when you book by Apr-30-2021**
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 Apr-30-2021**
Save $1,748 Photo of Luxury Villa with Staff near Florence
  • min $12,183/wk
  • max $17,478/wk
  • min $10,965/wk
  • max $15,730/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,748 when you book by Apr-30-2021**
" The staff were excellent and the property was beautiful. We had a few issues with no water on the first night. The manager fixed the water issue very promptly. The..." - Treena
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 Apr-30-2021**
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 Apr-30-2021**
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 Apr-30-2021**
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 Apr-30-2021**
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 Apr-30-2021**
Save $1,677 Photo of Villa Rental in Tuscany, Tavarnelle in val di Pesa
  • min $9,478/wk
  • max $16,772/wk
  • min $8,530/wk
  • max $15,095/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Washing Machine
  • Air Conditioning
** Save up to $1,677 when you book by Apr-30-2021**
Save $2,042 Photo of Villa Rental in Tuscany, Strada in Chianti
  • min $11,669/wk
  • max $20,419/wk
  • min $10,502/wk
  • max $18,377/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $2,042 when you book by Apr-30-2021**
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 Apr-30-2021**
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 Apr-30-2021**
Save $4,947 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $26,078/wk
  • max $49,471/wk
  • min $23,470/wk
  • max $44,524/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,947 when you book by Apr-30-2021**
 
Displaying 151 to 180 of 165 villas

Show all 206 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..