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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 179 villas
Save $391 Photo of Villa Rental in Tuscany, San Casciano in Val di Pesa (Chianti Area)
  • min $1,226/wk
  • max $2,059/wk
  • min $1,103/wk
  • max $1,668/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 $391 when you book by Dec-20-2018**
" Wonderful, bucolic setting --just what we needed to relax and get away from it all...." - Barbara
Save $391 Photo of Apartment Rental in Tuscany, San Casciano in Val di Pesa (Chianti Area)
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/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 $391 when you book by Dec-20-2018**
" Our experience was amazing!!! Property is pristine in the middle of the country with beautiful walking paths and roads around. ..." - Kamellia
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 Dec-20-2018**
" Excellent. Beautiful house and property...." - Gary
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 Dec-20-2018**
Save $317 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $993/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 $317 when you book by Dec-20-2018**
" 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 $266 Photo of Tuscany Vacation Villa
  • min $1,541/wk
  • max $2,661/wk
  • min $1,387/wk
  • max $2,395/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $266 when you book by Dec-20-2018**
" It was wonderful. ..." - Cathie
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 Dec-20-2018**
"The building itself, the surroundings, and Tuscany in general...." - Pawel
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 Dec-20-2018**
Save $196 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Dec-20-2018**
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 Dec-20-2018**
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 Dec-20-2018**
" We loved this place. We loved the beauty, areas to walk, small town nearby, great local restaurants and convenience to cities...." - Linda
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 Dec-20-2018**
" 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 $4,487 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $23,519/wk
  • max $44,865/wk
  • min $21,167/wk
  • max $40,379/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 $4,487 when you book by Dec-20-2018**
Save $482 Photo of Charming Apartments in Tuscany Perfect for a Family Holiday
  • min $2,085/wk
  • max $4,816/wk
  • min $1,877/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 Dec-20-2018**
Save $256 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $2,002/wk
  • max $2,560/wk
  • min $1,802/wk
  • max $2,304/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 $256 when you book by Dec-20-2018**
" 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 Dec-20-2018**
" 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 $205 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $676/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $205 when you book by Dec-20-2018**
" Very unique and attractive...." - Jorge
Save $205 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $676/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $205 when you book by Dec-20-2018**
" An experience of a lifetime! Fantastic from any angle or view! ..." - Karen
Save $445 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $1,738/wk
  • max $4,451/wk
  • min $1,564/wk
  • max $4,006/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $445 when you book by Dec-20-2018**
" Fabulous...." - Jane
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 Dec-20-2018**
" It was absolutely fabulous!..." - Paula
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 Dec-20-2018**
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 Dec-20-2018**
" It was great!..." - Jennifer
Save $317 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $993/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 $317 when you book by Dec-20-2018**
" 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 $261 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,030/wk
  • max $1,373/wk
  • min $834/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 $261 when you book by Dec-20-2018**
" Fantastic!..." - Sam
Save $205 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $834/wk
  • max $1,079/wk
  • min $676/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 $205 when you book by Dec-20-2018**
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 Dec-20-2018**
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Air Conditioning
Save $3,938 Photo of Elegant Chianti Villa with Pool close to Florence
  • $19,688/wk
  • $17,719/wk
  • Min Stay: 14 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 Dec-20-2018**
 
Displaying 151 to 180 of 179 villas

Show all 225 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..