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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 170 villas
  • min $756/wk
  • max $1,386/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • min $1,260/wk
  • max $2,450/wk
  • Min Stay: 3 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $7,616/wk
  • max $11,603/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Amazing. We has a wonderful time. ..." - Tim
  • min $2,734/wk
  • max $4,428/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,078/wk
  • max $2,188/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Comfortable...." - Jess
  • min $1,787/wk
  • max $3,219/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $615/wk
  • max $2,748/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Outstanding and memorable experience for all of us...." - Bruce
  • min $1,418/wk
  • max $8,490/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 $1,519/wk
  • max $3,079/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $2,311/wk
  • max $4,761/wk
  • Min Stay: 3 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our overall experience was very positive. We had a great time whether we were relaxing by the villa or exploring a city or town on a day trip. The villa offers p..." - Lynne
  • 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
Save $1,067 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $8,876/wk
  • max $14,349/wk
  • min $7,988/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 $1,067 when you book by Jun-30-2018**
Save $1,039 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $8,652/wk
  • max $14,000/wk
  • min $7,787/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 15 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,039 when you book by Jun-30-2018**
  • 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
Save $988 Photo of Private Country Estate in Tuscany
  • min $8,078/wk
  • max $13,566/wk
  • min $7,270/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $988 when you book by Jun-30-2018**
" 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 $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 $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 $5,627/wk
  • max $6,560/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • 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 $532/wk
  • max $1,120/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
"The building itself, the surroundings, and Tuscany in general...." - Pawel
 
Displaying 151 to 180 of 170 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..