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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 Jan-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 Jan-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 Jan-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 Jan-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 $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 Jan-20-2020**
" It was an experience of a lifetime - just awesome!..." - Carmita
Save $391 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $391 when you book by Jan-20-2020**
" Perfect. ..." - Mario
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 Jan-20-2020**
" The view and being in a small town. ..." - Joseph
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 Jan-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 $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 Jan-20-2020**
" Wonderful!..." - Chuck
Save $2,188 Photo of Grand Villa with Private Pool Overlooking Tuscan Vineyards
  • $21,878/wk
  • $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 $2,188 when you book by Jan-20-2020**
" Excellent. Best way to find the Villa was to use the Waze app. Simple...." - Alan
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 Jan-20-2020**
" Enjoyed the villa and its location in the small town very much...." - Richard P
Save $1,098 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $5,488/wk
  • max $10,976/wk
  • min $4,939/wk
  • max $9,878/wk
  • Min Stay: 4 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 15 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,098 when you book by Jan-20-2020**
Save $154 Photo of Holiday Accommodation in Chianti
  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jan-20-2020**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
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 Jan-20-2020**
" Our stay was the highlight of our trip to Italy. ..." - Patty
Save $154 Photo of Holiday Accommodation in Chianti
  • 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 Jan-20-2020**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $1,750 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $9,100/wk
  • max $17,500/wk
  • min $8,190/wk
  • max $15,750/wk
  • Min Stay: 4 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,750 when you book by Jan-20-2020**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,470/wk
  • max $1,960/wk
  • min $1,323/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Jan-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 Jan-20-2020**
" It was wonderful. ..." - Cathie
Save $330 Photo of Tuscan Villa with a Private Pool in a Village
  • min $693/wk
  • max $3,296/wk
  • min $624/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 Jan-20-2020**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
Save $529 Photo of Charming Tuscan Villa on Large Estate
  • min $2,646/wk
  • max $5,292/wk
  • min $2,381/wk
  • max $4,763/wk
  • Min Stay: 4 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $529 when you book by Jan-20-2020**
" Excellent...." - Colin
Save $2,310 Photo of Villa Rental in Tuscany, Castelfalfi
  • 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 Jan-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 Jan-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 $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 Jan-20-2020**
" 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
Save $980 Photo of Villa Rental in Tuscany, Gambassi Terme
  • 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 Jan-20-2020**
" Overall we had a good week. ..." - Phil
Save $4,947 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $26,078/wk
  • max $49,471/wk
  • min $23,470/wk
  • max $44,524/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,947 when you book by Jan-20-2020**
Save $1,362 Photo of Private Country Estate in Tuscany
  • min $5,558/wk
  • max $13,622/wk
  • min $5,002/wk
  • max $12,260/wk
  • Min Stay: 4 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,362 when you book by Jan-20-2020**
" Absolutely beautiful with a nice Tuscan feel. The pool and outdoor loggia were very lovely. We spent a lot of time outside with wine and watching a beautiful sunse..." - Sujata
Save $293 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,235/wk
  • max $2,933/wk
  • min $1,112/wk
  • max $2,640/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $293 when you book by Jan-20-2020**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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
** Save up to $211 when you book by Jan-20-2020**
Save $213 Photo of Apartment Rental in Tuscany, Gambassi Terme
  • min $923/wk
  • max $2,132/wk
  • min $831/wk
  • max $1,919/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $213 when you book by Jan-20-2020**
Save $1,442 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $5,880/wk
  • max $14,420/wk
  • min $5,292/wk
  • max $12,978/wk
  • Min Stay: 4 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,442 when you book by Jan-20-2020**
" Wonderful...." - Naomi
 
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..