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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 $2,020 Photo of Private Country Estate in Tuscany
  • min $8,078/wk
  • max $13,566/wk
  • min $6,059/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,020 when you book by Feb-28-2018**
" 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
  • min $1,418/wk
  • max $8,018/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a great time...." - Robert
  • min $3,613/wk
  • max $6,088/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
  • min $2,868/wk
  • max $4,095/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • min $12,824/wk
  • max $19,488/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Superb villa. Probably Top Ten in Tuscany and Top Five for large groups...." - Samuel
  • min $2,352/wk
  • max $4,480/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was great! We would love to go back...." - Diana
  • min $2,976/wk
  • max $5,251/wk
  • Min Stay: 7 days
Sleeps 7 to 8 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" My clients loved the property! They spent many hours visiting in the kitchen while they cooked...." - Linda
  • min $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" Our experience was amazing!!! Property is pristine in the middle of the country with beautiful walking paths and roads around. ..." - Kamellia
  • min $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful, bucolic setting --just what we needed to relax and get away from it all...." - Barbara
Save $1,033 Photo of Charming Tuscan Villa on Large Estate
  • min $3,290/wk
  • max $5,950/wk
  • min $2,468/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,033 when you book by Feb-28-2018**
  • min $5,992/wk
  • max $8,960/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $17,345/wk
  • max $21,415/wk
  • Min Stay: 3 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $756/wk
  • max $1,260/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • min $1,042/wk
  • max $2,819/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $8,978/wk
  • max $12,628/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $961/wk
  • max $1,205/wk
  • Min Stay: 7 days
Sleeps 2 people
  • Studio and/or Loft
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $986/wk
  • max $1,307/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
 
Displaying 151 to 180 of 168 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. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..