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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 >

Showing 1 to 30 of 177 properties
  • min $2,190/wk
  • max $4,130/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Excellent. Our hosts were magnificent. I wanted the experience of a stay in a Tuscany villa, and we got exactly that. Also, we paid for our hosts to prepare a m..." - Samuel
  • min $1,797/wk
  • max $3,081/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was wonderful! Exceeded our expectations!..." - Kathleen
  • min $1,702/wk
  • max $2,941/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We loved our home for the week. Elizabeth was so wonderful and welcoming. We enjoyed the fireplace and loved our outdoor terrac, especially for al fresco dining...." - Suzanne
  • min $5,227/wk
  • max $7,281/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" GOOD! Unseasonal heat was a bit of a problem, but the fans provided were a real asset and quite used --- 24 hours per day! ..." - Kurt
  • min $1,797/wk
  • max $3,081/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our trip was fabulous! Many laughs, great food and wine, and breathtaking views...." - Claudia
  • min $1,471/wk
  • max $1,891/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Magical! We loved the villa. It was everything I hoped Tuscany to be. ..." - Bruce Moe And Carol Ferioli
  • max $2,562/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Exceptionally comfortable and enticing...." - Joan
  • min $1,414/wk
  • max $4,242/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" A good place to get together with family. We enjoyed visiting the great region of Chianti. ..." - Jacques
  • min $981/wk
  • max $1,601/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a very pleasant week. The property was as described and everything worked well, location was perfect, the hosts were friendly and helpful as were the other..." - Ian
  • min $1,037/wk
  • max $1,275/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic!..." - Sam
  • min $2,604/wk
  • max $3,920/wk
  • Min Stay: 4 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Oustanding, awesome, and amazing. Everything about the villa and the estate exceeded our expectations. The views from every direction were breathtaking and the v..." - Leeanne
  • min $1,681/wk
  • max $2,861/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
Save $1,456
  • min $7,001/wk
  • max $11,128/wk
  • min $5,601/wk
  • max $10,015/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,456 when you book by Jan-31-2016**
  • min $771/wk
  • max $1,541/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a lovely stay and it was perfect to visit the surrounding areas...." - Ralph
  • min $2,941/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" I felt as if I was in a movie set...very scenic, peaceful and comfortable!..." - Derek
  • min $1,294/wk
  • max $2,354/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Air Conditioning
" Very enjoyable authentic experience in small town Italy...." - Catherine
  • min $5,601/wk
  • max $9,802/wk
  • Min Stay: 3 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The property is wonderful. The home is nicely decorated and the rooms are very spacious. We loved the big dining room and large sitting rooms for our big group. ..." - Kara
  • min $2,991/wk
  • max $5,323/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had an outstanding experience. The villa was even better than the photos indicated, the view was amazing, and Ida and Renato were lovely hosts. ..." - Graeme
  • min $1,401/wk
  • max $2,241/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a really pleasant break - Sole 2 was so comfortable and peaceful - and had excellent outdoor flow with outside dining facilities and a great uncrowded swimm..." - Peter
  • min $1,471/wk
  • max $1,891/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" Check-in and check-out was very smooth. Staff were wonderful and responded quickly to our inquiries and requests. ..." - Sheila
  • min $981/wk
  • max $1,601/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Great...." - Tom
  • min $699/wk
  • max $1,309/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was about an 8 on a scale of 10...." - Stan
  • min $835/wk
  • max $1,623/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
  • min $539/wk
  • max $994/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,471/wk
  • max $1,891/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
" Our visit was everything one could hope for in a vacation. Machiavelli - Canonica 1 is near perfect. If you offered a "Most Excellent" review category..." - Phil
  • min $9,660/wk
  • max $14,980/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Amazing. There were eight of us and we all had the same positive experience!..." - Maureen
  • min $781/wk
  • max $1,241/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Great experience overall. Hard to find in the dark, but several calls to Cecile, the ever-helpful property manager, enabled us to navigate to the right spot. The..." - Isaac
  • min $11,270/wk
  • max $17,290/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Wonderful...." - Jackie
  • min $4,481/wk
  • max $6,861/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 $813/wk
  • max $995/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
" Very unique and attractive...." - Jorge
 
Showing 1 to 30 of 177 properties

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..