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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 180 villas
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 Sep-30-2018**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
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 Sep-30-2018**
" An experience of a lifetime! Fantastic from any angle or view! ..." - Karen
Save $1,470 Photo of Rural Woodland Tuscan villa with Pool and BBQ near Montaione
  • min $8,402/wk
  • max $14,702/wk
  • min $7,562/wk
  • max $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 Sep-30-2018**
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 Sep-30-2018**
" Fantastic!..." - Sam
Save $630 Photo of Tuscany Vacation Rental
  • min $4,200/wk
  • max $6,300/wk
  • min $3,780/wk
  • max $5,670/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $630 when you book by Sep-30-2018**
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 Sep-30-2018**
" The setting is very quaint. ..." - Mike
Save $121 Photo of Family-Friendly Apartment with Charm and Comfort in the Chianti Region
  • min $961/wk
  • max $1,205/wk
  • min $865/wk
  • max $1,085/wk
  • Min Stay: 7 days
Sleeps 2 people
  • Studio and/or Loft
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $121 when you book by Sep-30-2018**
Save $202 Photo of Family-Friendly Apartment with Charm and Comfort in the Chianti Region
  • min $1,357/wk
  • max $2,017/wk
  • min $1,221/wk
  • max $1,815/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $202 when you book by Sep-30-2018**
" It was absolutely fabulous!..." - Paula
Save $189 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,071/wk
  • max $1,890/wk
  • min $964/wk
  • max $1,701/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $189 when you book by Sep-30-2018**
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 Sep-30-2018**
" 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 Sep-30-2018**
" Very unique and attractive...." - Jorge
Save $3,938 Photo of Elegant Chianti Villa with Pool close to Florence
  • max $22,750/wk
  • max $20,475/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,938 when you book by Sep-30-2018**
Save $1,050 Photo of Luxury  Villa  with  Pool  in  Chianti  near  wineries,  historic  attractions.
  • min $9,184/wk
  • max $10,496/wk
  • min $8,266/wk
  • max $9,446/wk
  • Min Stay: 7 days
Sleeps 14 to 15 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,050 when you book by Sep-30-2018**
Save $1,162 Photo of Villa Rental in Tuscany, Montaione
  • min $8,820/wk
  • max $11,620/wk
  • min $7,938/wk
  • max $10,458/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,162 when you book by Sep-30-2018**
Save $1,263 Photo of Beautiful Tuscan Villa with Tower and Private Swimming Pool near Florence
  • min $8,978/wk
  • max $12,628/wk
  • min $8,080/wk
  • max $11,365/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,263 when you book by Sep-30-2018**
Save $237 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $2,002/wk
  • max $2,366/wk
  • min $1,802/wk
  • max $2,129/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $237 when you book by Sep-30-2018**
" The villa was very nice. Spacious and well appointed. The setting was beautiful. The villa itself was very close to a road that took some getting used to...." - alan
Save $811 Photo of Farmhouse for Rent in Tuscany
  • min $2,611/wk
  • max $8,106/wk
  • min $2,350/wk
  • max $7,295/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $811 when you book by Sep-30-2018**
" Absolutely wonderful. It was beautiful, and peaceful, and comfortable. The swimming pool was large and clean and refreshing. My husband loved the outdoor shower! F..." - Michele
Save $202 Photo of Family-Friendly Apartment with Charm and Comfort in the Chianti Region
  • min $1,357/wk
  • max $2,017/wk
  • min $1,221/wk
  • max $1,815/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $202 when you book by Sep-30-2018**
Save $460 Photo of Family-Friendly Villa with Charm and Comfort in the Chianti Region
  • min $3,316/wk
  • max $4,596/wk
  • min $2,984/wk
  • max $4,136/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $460 when you book by Sep-30-2018**
" Great Villa to rent. We took the entire main house, which can be subdivided into three units. There were two kitchens in the house, and they were able to accomodat..." - Lloyd
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 Sep-30-2018**
" 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
Save $118 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $532/wk
  • max $1,176/wk
  • min $479/wk
  • max $1,058/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Sep-30-2018**
"The building itself, the surroundings, and Tuscany in general...." - Pawel
Save $1,743 Photo of Villa Rental in Tuscany, Montaione
  • min $13,650/wk
  • max $17,430/wk
  • min $12,285/wk
  • max $15,687/wk
  • Min Stay: 7 days
Sleeps 12 to 13 people
  • 6 double bedrooms
  • 6 bathrooms
** Save up to $1,743 when you book by Sep-30-2018**
Save $644 Photo of Villa Rental in Tuscany, Montaione
  • min $5,460/wk
  • max $6,440/wk
  • min $4,914/wk
  • max $5,796/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Air Conditioning
** Save up to $644 when you book by Sep-30-2018**
Save $477 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $1,630/wk
  • max $4,766/wk
  • min $1,467/wk
  • max $4,289/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $477 when you book by Sep-30-2018**
Save $477 Photo of Farmhouse Rental in Tuscany, Gambassi Terme
  • min $1,630/wk
  • max $4,766/wk
  • min $1,467/wk
  • max $4,289/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $477 when you book by Sep-30-2018**
Save $656 Photo of Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione
  • min $5,627/wk
  • max $6,560/wk
  • min $5,064/wk
  • max $5,904/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $656 when you book by Sep-30-2018**
Save $896 Photo of Tuscan Villa with Private Pool on an Olive Oil Estate
  • min $5,992/wk
  • max $8,960/wk
  • min $5,393/wk
  • max $8,064/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $896 when you book by Sep-30-2018**
Save $160 Photo of Family-Friendly Apartment with Charm and Comfort in the Chianti Region
  • min $1,119/wk
  • max $1,601/wk
  • min $1,007/wk
  • max $1,441/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 $160 when you book by Sep-30-2018**
" We loved this place. We loved the beauty, areas to walk, small town nearby, great local restaurants and convenience to cities...." - Linda
Save $192 Photo of Family-Friendly Apartment with Charm and Comfort in the Chianti Region
  • min $1,297/wk
  • max $1,920/wk
  • min $1,167/wk
  • max $1,728/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $192 when you book by Sep-30-2018**
" It was great!..." - Jennifer
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 Sep-30-2018**
 
Displaying 151 to 180 of 180 villas

Show all 228 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. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..