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Vacation Accommodation Chianti Tuscany Villa 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 1 to 30 of 177 villas
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,337/wk
  • min $1,971/wk
  • max $3,903/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $434 when you book by Oct-20-2019**
" It was magical. When you arrive and open the gate, you are surrounded by roses, hydrangeas, geraniums (with colors I'd never seen) and olive trees. The Villa..." - Joan
Save $327 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,075/wk
  • max $3,267/wk
  • min $1,868/wk
  • max $2,940/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $327 when you book by Oct-20-2019**
" Completely and utterly wonderful...." - Christopher
Save $996 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,495/wk
  • max $3,202/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $996 when you book by Oct-20-2019**
" We loved our stay! The location is perfect and very peaceful. With a car everything is close and accessible. The villa was big for our family of 4 but we loved it...." - Pia
Save $784 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $7,841/wk
  • min $5,041/wk
  • max $7,057/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $784 when you book by Oct-20-2019**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $560 Photo of Tuscany Villa Rental near Greve
  • min $2,941/wk
  • max $5,601/wk
  • min $2,647/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Oct-20-2019**
" Our stay was the highlight of our trip to Italy. ..." - Patty
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Oct-20-2019**
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
Save $155 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Oct-20-2019**
" It was an experience of a lifetime - just awesome!..." - Carmita
Save $1,080 Photo of Villa Rental in Tuscany, Montespertoli (Chianti Area)
  • min $6,400/wk
  • max $10,801/wk
  • min $5,760/wk
  • max $9,721/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,080 when you book by Oct-20-2019**
Save $254 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,289/wk
  • max $2,539/wk
  • min $1,160/wk
  • max $2,285/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $254 when you book by Oct-20-2019**
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
Save $314 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,625/wk
  • max $3,137/wk
  • min $1,463/wk
  • max $2,823/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $314 when you book by Oct-20-2019**
" Excellent. Beautiful house and property...." - Gary
Save $570 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,032/wk
  • max $5,701/wk
  • min $3,629/wk
  • max $5,131/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $570 when you book by Oct-20-2019**
Save $221 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,205/wk
  • min $1,361/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Oct-20-2019**
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
Save $512 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
  • min $2,651/wk
  • max $5,116/wk
  • min $2,386/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 Oct-20-2019**
" 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 $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,451/wk
  • max $1,960/wk
  • min $1,306/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Oct-20-2019**
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,132/wk
  • min $831/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Oct-20-2019**
Save $2,916 Photo of Ancient Hamlet in Tuscany near Florence
  • min $18,944/wk
  • max $29,155/wk
  • min $17,050/wk
  • max $26,240/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,916 when you book by Oct-20-2019**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,451/wk
  • max $1,960/wk
  • min $1,306/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $196 when you book by Oct-20-2019**
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,107/wk
  • min $1,447/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $211 when you book by Oct-20-2019**
Save $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,891/wk
  • min $1,447/wk
  • max $2,602/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Oct-20-2019**
" Luigi and his staff were great. Friendly and responsive...." - John
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,132/wk
  • min $831/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
** Save up to $213 when you book by Oct-20-2019**
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,132/wk
  • min $831/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Oct-20-2019**
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,132/wk
  • min $831/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Oct-20-2019**
Save $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $2,107/wk
  • max $2,891/wk
  • min $1,896/wk
  • max $2,602/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Oct-20-2019**
" Our experience surpassed our expectation. The property is charming, beautiful, spacious and is more beautiful than the online brochure. The house itself was also c..." - Chris
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,608/wk
  • max $2,107/wk
  • min $1,447/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Oct-20-2019**
" Absolutely wonderful vacation! ..." - Dean
Save $330 Photo of Tuscan Villa with a Private Pool in a Village
  • min $693/wk
  • max $3,296/wk
  • min $624/wk
  • max $2,966/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $330 when you book by Oct-20-2019**
" We stayed there for a summer in 2009 it was a wonderful experience then and again this visit. We know the rhythm of the village so enjoy all it has to offer..." - Joy
Save $980 Photo of Villa Rental in Tuscany, Gambassi Terme
  • min $6,791/wk
  • max $9,802/wk
  • min $6,112/wk
  • max $8,822/wk
  • Min Stay: 3 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $980 when you book by Oct-20-2019**
" Overall we had a good week. ..." - Phil
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,088/wk
  • max $1,960/wk
  • min $979/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Oct-20-2019**
Save $127 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,274/wk
  • min $838/wk
  • max $1,147/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $127 when you book by Oct-20-2019**
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Oct-20-2019**
" It was the most wonderful place. So very near Firenze and yet in the quiet and lovely countryside. The administrator was very helpful and charming. We enjoy every ..." - Susana
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,421/wk
  • min $838/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Oct-20-2019**
 
Displaying 1 to 30 of 177 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..