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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 168 villas
  • min $2,190/wk
  • max $4,130/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was fantastic and everything I hoped it would be. The villa is beautiful and looks exactly as the pictures show it. The setting is spectacular and looking out..." - Lucy
  • min $2,107/wk
  • max $2,820/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Our stay was wonderful. The villa is beautiful inside and out. It is surrounded by olive groves and vineyards. The hosts Emma, Giancarlo, and Matteo greeted us at..." - Carolyn
  • 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 $673/wk
  • max $971/wk
  • Min Stay: 7 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
  • min $966/wk
  • max $1,232/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
  • min $1,471/wk
  • max $2,573/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" This was a perfect holiday location to experience the delights of Tuscany...." - Prudence
  • 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 $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
  • min $22,371/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 $834/wk
  • max $1,079/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" An experience of a lifetime! Fantastic from any angle or view! ..." - Karen
  • min $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" 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
  • min $1,471/wk
  • max $2,059/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" Amazing, would return tomorrow...." - Marcie
  • 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
  • max $36,933/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $1,226/wk
  • max $1,667/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" Very nice...." - Marty
  • 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 $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 $4,411/wk
  • max $6,371/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved everything about it. It was the perfect place to spend Christmas with our family. It was very roomy, and the separate apartment in the basement was nice t..." - Holly
  • min $1,357/wk
  • max $2,017/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was absolutely fabulous!..." - Paula
  • 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 $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
" Location was terrific. We loved being able to walk to a market, wine shop, several restaurants, coffee cafes, and historical points. Hostess was exceptionally resp..." - Maryann
  • min $1,289/wk
  • max $2,483/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very good. Owners were very accessible and accommodating. The vendemmia (grape harvest) was on at the time in their fields and they invited us to see the harvest a..." - Fran
  • min $1,119/wk
  • max $1,601/wk
  • Min Stay: 7 days
Sleeps 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved this place. We loved the beauty, areas to walk, small town nearby, great local restaurants and convenience to cities...." - Linda
  • min $12,317/wk
  • max $17,673/wk
  • Min Stay: 3 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The staff were excellent and the property was beautiful. We had a few issues with no water on the first night. The manager fixed the water issue very promptly. The..." - Treena
  • min $1,357/wk
  • max $2,017/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $514/wk
  • max $965/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,961/wk
  • max $4,947/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fabulous...." - Tom
  • $11,622/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" The house was beautiful, and really well appointed. Gorgeous glasses, dishes, furnishings, etc...." - Rachel
  • 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 wonderful 2 weeks with friends and family and would love to return again. This vacation was among the best ever...." - Jan
  • min $1,541/wk
  • max $2,661/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
" It was wonderful. ..." - Cathie
 
Displaying 1 to 30 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..