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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
Save $784
  • 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 Sep-20-2020**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $366
  • min $2,077/wk
  • max $3,662/wk
  • min $1,869/wk
  • max $3,296/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $366 when you book by Sep-20-2020**
" 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 $327
  • min $2,440/wk
  • max $3,267/wk
  • min $2,196/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 Sep-20-2020**
" Our overall experience staying at Donatella was simply fantastic. The villa is just beautiful. The accommodations were so nice and very comfortable. The views were..." - George
Save $345
  • min $1,888/wk
  • max $3,448/wk
  • min $1,699/wk
  • max $3,103/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $345 when you book by Sep-20-2020**
" Our experience was very soul-refreshing with the family at La Solaia. We enjoyed the location and the home. The kitchen was stocked with enough basic equipment to ..." - Dana
Save $409
  • min $2,293/wk
  • max $4,093/wk
  • min $2,064/wk
  • max $3,684/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $409 when you book by Sep-20-2020**
" Wonderful all around!..." - Cinnamon
Save $2,366
  • min $13,302/wk
  • max $23,663/wk
  • min $11,972/wk
  • max $21,297/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,366 when you book by Sep-20-2020**
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
Save $1,033
  • $10,327/wk
  • $9,294/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,033 when you book by Sep-20-2020**
" Exceptional villa...." - Jerry
Save $971
  • 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 Sep-20-2020**
" 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 $749
  • min $4,760/wk
  • max $7,490/wk
  • min $4,284/wk
  • max $6,741/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $749 when you book by Sep-20-2020**
" Wonderful..." - Aline
Save $448
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Sep-20-2020**
" Outstanding! The villa was even better than it looked in the pictures on the website. Check in was very easy and staff were very helpful in answering any questions..." - Julie
Save $211
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/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 Sep-20-2020**
Save $211
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/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 Sep-20-2020**
Save $1,208
  • min $5,251/wk
  • max $12,077/wk
  • min $4,726/wk
  • max $10,869/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,208 when you book by Sep-20-2020**
" The villa was absolutely wonderful - elegant and comfortable, plenty of room for everyone. The outside spaces were fantastic (if a bit buggy). The location was ide..." - Mary
Save $154
  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Sep-20-2020**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $315
  • min $1,634/wk
  • max $3,149/wk
  • min $1,471/wk
  • max $2,834/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $315 when you book by Sep-20-2020**
" The property was great but rather far from town...." - Betty
Save $252
  • min $1,961/wk
  • max $2,521/wk
  • min $1,765/wk
  • max $2,269/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $252 when you book by Sep-20-2020**
" It was wonderful. ..." - Cathie
Save $1,330
  • min $9,102/wk
  • max $13,302/wk
  • min $8,192/wk
  • max $11,972/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,330 when you book by Sep-20-2020**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $2,310
  • min $14,630/wk
  • max $23,100/wk
  • min $13,167/wk
  • max $20,790/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,310 when you book by Sep-20-2020**
Save $162
  • min $769/wk
  • max $1,622/wk
  • min $692/wk
  • max $1,460/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Sep-20-2020**
Save $658
  • min $5,040/wk
  • max $6,580/wk
  • min $4,536/wk
  • max $5,922/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $658 when you book by Sep-20-2020**
Save $448
  • min $1,961/wk
  • max $4,481/wk
  • min $1,765/wk
  • max $4,033/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $448 when you book by Sep-20-2020**
" The setting is very quaint. ..." - Mike
Save $196
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Sep-20-2020**
" The property is very good and comfortable. Gina is the perfect host and the facilities are excellent...." - GARRY
Save $1,470
  • min $8,402/wk
  • max $14,702/wk
  • min $7,562/wk
  • max $13,232/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,470 when you book by Sep-20-2020**
Save $2,560
  • min $20,797/wk
  • max $25,599/wk
  • min $18,717/wk
  • max $23,039/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,560 when you book by Sep-20-2020**
Save $980
  • 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 Sep-20-2020**
" Overall we had a good week. ..." - Phil
Save $2,788
  • min $21,878/wk
  • max $21,878/wk
  • min $19,090/wk
  • max $19,690/wk
  • Min Stay: 3 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,788 when you book by Sep-20-2020**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
Save $1,155
  • min $4,323/wk
  • max $11,550/wk
  • min $3,891/wk
  • max $10,395/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,155 when you book by Sep-20-2020**
" SPECTACULAR!..." - Linda
Save $1,482
  • min $10,381/wk
  • max $14,819/wk
  • min $9,343/wk
  • max $13,337/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,482 when you book by Sep-20-2020**
Save $776
  • min $4,369/wk
  • max $7,755/wk
  • min $3,932/wk
  • max $6,980/wk
  • Min Stay: 4 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $776 when you book by Sep-20-2020**
" It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
Save $196
  • min $1,681/wk
  • max $1,961/wk
  • min $1,513/wk
  • max $1,765/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $196 when you book by Sep-20-2020**
 
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..