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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 169 villas
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,337/wk
  • min $2,070/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 Jul-20-2020**
" 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 $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 Jul-20-2020**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $356 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,869/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 $356 when you book by Jul-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 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • 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 Jul-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 $938 Photo of Traditional Tuscan Villa on a Large Estate
  • min $3,738/wk
  • max $9,380/wk
  • min $3,364/wk
  • max $8,442/wk
  • Min Stay: 4 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $938 when you book by Jul-20-2020**
" Wonderful!..." - Chuck
Save $330 Photo of Tuscan Villa with a Private Pool in a Village
  • min $924/wk
  • max $3,296/wk
  • min $832/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 Jul-20-2020**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
Save $324 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,699/wk
  • max $2,912/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $324 when you book by Jul-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 $396 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $2,064/wk
  • max $3,567/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 $396 when you book by Jul-20-2020**
" Wonderful all around!..." - Cinnamon
Save $282 Photo of Apartment Rental in Chianti Tuscany
  • min $1,718/wk
  • max $2,820/wk
  • min $1,546/wk
  • max $2,538/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $282 when you book by Jul-20-2020**
" 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
Save $2,366 Photo of Large Luxury Villa Rental in the Chianti with Spectacular Views
  • 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 Jul-20-2020**
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
Save $108 Photo of Tuscan Apartment in Historic Castle
  • min $541/wk
  • max $1,081/wk
  • min $487/wk
  • max $973/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $108 when you book by Jul-20-2020**
Save $155 Photo of Charming Apartment in Chianti Overlooking the Countryside
  • 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 Jul-20-2020**
" The view and being in a small town. ..." - Joseph
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 Jul-20-2020**
" It was an experience of a lifetime - just awesome!..." - Carmita
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 Jul-20-2020**
Save $146 Photo of Charming 14th Century Apartment in the Center of a Medieval Town in Tuscany
  • $1,458/wk
  • $1,312/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $146 when you book by Jul-20-2020**
" The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
Save $2,788 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • 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 Jul-20-2020**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
Save $124 Photo of Tuscan Apartment in Historic Castle
  • min $587/wk
  • max $1,235/wk
  • min $528/wk
  • max $1,112/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $124 when you book by Jul-20-2020**
" Love this property. Second year in a row I have been there...." - Sadia
Save $1,033 Photo of Luxury Chianti Villa on a Wine Estate
  • $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 Jul-20-2020**
" Exceptional villa...." - Jerry
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 Jul-20-2020**
" Our stay was the highlight of our trip to Italy. ..." - Patty
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • 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 Jul-20-2020**
Save $252 Photo of Tuscany Vacation Villa
  • 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 Jul-20-2020**
" It was wonderful. ..." - Cathie
Save $149 Photo of CastleApartment Rental in Tuscany, Montagnana
  • min $871/wk
  • max $1,489/wk
  • min $784/wk
  • max $1,340/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $149 when you book by Jul-20-2020**
" Outstanding! The property and the villa were absolutely perfect and everything we hoped it would be!..." - Dana
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • 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 Jul-20-2020**
Save $185 Photo of Tuscan Apartment in Historic Castle
  • min $850/wk
  • max $1,853/wk
  • min $765/wk
  • max $1,668/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $185 when you book by Jul-20-2020**
Save $139 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,392/wk
  • min $695/wk
  • max $1,253/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $139 when you book by Jul-20-2020**
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
Save $139 Photo of Tuscan Apartment in Historic Castle
  • min $685/wk
  • max $1,392/wk
  • min $616/wk
  • max $1,253/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $139 when you book by Jul-20-2020**
Save $120 Photo of Cozy Apartment Rental in the Chianti Area
  • min $766/wk
  • max $1,195/wk
  • min $689/wk
  • max $1,076/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $120 when you book by Jul-20-2020**
" Enjoyed the villa and its location in the small town very much...." - Richard P
Save $155 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,545/wk
  • min $695/wk
  • max $1,391/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Jul-20-2020**
" We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
Save $132 Photo of Tuscan Apartment in Historic Castle
  • min $696/wk
  • max $1,315/wk
  • min $626/wk
  • max $1,184/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $132 when you book by Jul-20-2020**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,622/wk
  • min $695/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 Jul-20-2020**
 
Displaying 1 to 30 of 169 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..