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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 170 villas
Save $219 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,130/wk
  • min $1,971/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 $219 when you book by Aug-31-2018**
" We absolutely loved our stay. The views were exceptionally beautiful, with vineyards and olive groves as far as the eye could see, and church bells adding to the ..." - Denice
  • min $2,075/wk
  • max $2,967/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" This was incredible villa and overall experience. The villa itself was more beautiful then the pictures portrayed, but the best part was the family that owned the..." - Thomas
  • min $5,601/wk
  • max $7,841/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We had a fantastic time at the villa. It was roomy enough to accommodate all 12 of us in 4 families. The grandkids loved having a room to themselves...." - Philip
  • min $1,888/wk
  • max $3,558/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We thoroughly enjoyed our two weeks in Villa Certaldo. We had stayed there 11 years ago and we enjoyed it more this time than we did the first and that is saying ..." - Jim
  • min $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Perfect. ..." - Mario
  • min $3,990/wk
  • max $5,250/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Excellent..." - Monica
  • min $1,785/wk
  • max $8,777/wk
  • Min Stay: 7 days
Sleeps 15 people
  • 1 single bedrooms
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Great week...." - Maria
  • min $1,888/wk
  • max $3,235/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful property. So serene and scenic. Easy to unwind and relax yet close to many exciting places to visit..." - Steven
  • min $2,084/wk
  • max $3,963/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Beautiful views of the countryside. Very Tuscan rural villa. Quiet and restful place...." - Genevieve
  • min $700/wk
  • max $1,545/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,512/wk
  • max $2,450/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
" We loved everything about our stay. Three couples stayed in Poggio 2. We were very comfortable--the 3 bedroom, 3 bath apartment was perfect. It was quiet and p..." - Mary
  • min $953/wk
  • max $1,550/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was a wonderful stay. The home was very spacious. We loved being right next to the adorable town of Barberino Val d'Elsa. The gated entry was a plus sinc..." - Erinn
  • 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
  • min $1,401/wk
  • max $1,625/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" One of our favourite areas on our month-long trip in Italy. After staying in Florence this was such a pleasant, quiet week with gorgeous scenery, pool and friendl..." - Susan
  • min $766/wk
  • max $1,195/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Enjoyed the villa and its location in the small town very much...." - Richard P
  • min $6,721/wk
  • max $9,708/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • min $1,718/wk
  • max $2,820/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a very nice stay, and we would stay there again. It was convenient to Florence and other cities. We spent our days away from the villa, so our time there ..." - Mather
  • min $23,519/wk
  • max $44,865/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,780/wk
  • max $2,945/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic, better than our high expectations!..." - Harri
  • min $1,119/wk
  • max $1,601/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very good. ..." - Darryl
  • min $4,032/wk
  • max $6,335/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $957/wk
  • max $1,738/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,071/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • min $1,030/wk
  • max $1,373/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic!..." - Sam
  • min $834/wk
  • max $1,079/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" Very unique and attractive...." - Jorge
  • min $4,481/wk
  • max $9,708/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
  • min $834/wk
  • max $1,079/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • min $831/wk
  • max $1,419/wk
  • Min Stay: 3 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
  • min $4,901/wk
  • max $9,102/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
  • min $2,002/wk
  • max $2,485/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
 
Displaying 1 to 30 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..