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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 121 to 150 of 169 villas
Save $137 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,030/wk
  • max $1,373/wk
  • min $927/wk
  • max $1,236/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $137 when you book by Feb-28-2021**
" Fantastic!..." - Sam
Save $1,568 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,100/wk
  • max $15,680/wk
  • min $8,190/wk
  • max $14,112/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,568 when you book by Feb-28-2021**
Save $237 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,939/wk
  • max $2,370/wk
  • min $1,745/wk
  • max $2,133/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $237 when you book by Feb-28-2021**
" Fantastic, better than our high expectations!..." - Harri
Save $382 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $2,451/wk
  • max $3,823/wk
  • min $2,206/wk
  • max $3,441/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
** Save up to $382 when you book by Feb-28-2021**
Save $512 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
  • min $2,727/wk
  • max $5,115/wk
  • min $2,454/wk
  • max $4,604/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $512 when you book by Feb-28-2021**
" Overall it was a great stay. Rooms were perfect for what we needed. Views are amazing. It is good for big groups of 10 or more. Big upstairs meeting room, plen..." - Jeff
Save $1,932 Photo of Historic Tuscan Villa on a Wine Estate in the Chianti Region
  • min $9,732/wk
  • max $19,323/wk
  • min $8,759/wk
  • max $17,391/wk
  • Min Stay: 7 days
Sleeps 13 to 14 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,932 when you book by Feb-28-2021**
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
Save $1,288 Photo of Private Country Estate in Tuscany
  • min $5,558/wk
  • max $12,880/wk
  • min $5,002/wk
  • max $11,592/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,288 when you book by Feb-28-2021**
" Absolutely beautiful with a nice Tuscan feel. The pool and outdoor loggia were very lovely. We spent a lot of time outside with wine and watching a beautiful sunse..." - Sujata
Save $175 Photo of Apartment in Tuscany in a Historic Castle
  • min $709/wk
  • max $1,752/wk
  • min $638/wk
  • max $1,577/wk
  • Min Stay: 3 days
Sleeps 3 people
  • Studio and/or Loft
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $175 when you book by Feb-28-2021**
" Excellent value for the price!..." - Rosemary
Save $1,015 Photo of Tuscany Villa to Rent
  • min $8,400/wk
  • max $10,150/wk
  • min $7,560/wk
  • max $9,135/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,015 when you book by Feb-28-2021**
" Overall it was very good to excellent...." - Jill
Save $108 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $751/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $108 when you book by Feb-28-2021**
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 Feb-28-2021**
Save $495 Photo of Family-Friendly Tuscan Villa with Private Pool
  • min $1,961/wk
  • max $4,947/wk
  • min $1,765/wk
  • max $4,452/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $495 when you book by Feb-28-2021**
" Fabulous...." - Tom
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 Feb-28-2021**
" 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 $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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
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 Feb-28-2021**
Save $206 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,324/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $206 when you book by Feb-28-2021**
" Perfect. ..." - Mario
Save $167 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $1,103/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $167 when you book by Feb-28-2021**
" Pure heaven! The place was beautifully restored and decorated, the setting was perfect, the staff were incredibly helpful and nice. We couldn't have asked for..." - Dana
Save $108 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $751/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $108 when you book by Feb-28-2021**
" Very unique and attractive...." - Jorge
Save $108 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $751/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $108 when you book by Feb-28-2021**
" An experience of a lifetime! Fantastic from any angle or view! ..." - Karen
Save $167 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $1,103/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $167 when you book by Feb-28-2021**
" It was SO beautiful and enchanting staying up in the Tuscan hills in a 9th century castle. Everyone was so friendly and helpful and the views from our windows wer..." - Linda
 
Displaying 121 to 150 of 169 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..