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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 $659 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,440/wk
  • max $3,467/wk
  • min $2,084/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 $659 when you book by Nov-30-2020**
" 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 $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 Nov-30-2020**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $366 Photo of Tuscany Villa Rental in Chianti
  • 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 Nov-30-2020**
" 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 $345 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • 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 Nov-30-2020**
" 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 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • 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 Nov-30-2020**
" Wonderful all around!..." - Cinnamon
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 Nov-30-2020**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • 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 Nov-30-2020**
" 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 Photo of Villa Rental in Tuscany, San Donato in Poggio
  • 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 Nov-30-2020**
" Wonderful..." - Aline
Save $2,153 Photo of Large Luxury Villa Rental in the Chianti with Spectacular Views
  • min $13,302/wk
  • max $21,528/wk
  • min $11,972/wk
  • max $19,375/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,153 when you book by Nov-30-2020**
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
Save $966 Photo of Traditional Tuscan Villa on a Large Estate
  • min $4,158/wk
  • max $9,660/wk
  • min $3,742/wk
  • max $8,694/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $966 when you book by Nov-30-2020**
" Wonderful!..." - Chuck
Save $1,208 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • 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 Nov-30-2020**
" 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 $1,115 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,319/wk
  • max $11,152/wk
  • min $6,587/wk
  • max $10,037/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,115 when you book by Nov-30-2020**
" The property is in a fabulous location with incredible 360 views- including a view to Florence. The house is over 500 years old but has been modernized with 7 bed..." - Robert
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 Nov-30-2020**
" Overall we had a good week. ..." - Phil
Save $2,916 Photo of Ancient Hamlet in Tuscany near Florence
  • min $21,952/wk
  • max $29,155/wk
  • min $19,757/wk
  • max $26,240/wk
  • Min Stay: 7 days
Sleeps 50 people
  • 25 double bedrooms
  • 25 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,916 when you book by Nov-30-2020**
" It was a wonderful experience from beginning to end. I can't express how much all my friends and family enjoyed their time at the property...." - Brendan
Save $1,271 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,215/wk
  • max $12,712/wk
  • min $7,393/wk
  • max $11,441/wk
  • Min Stay: 4 days
Sleeps 19 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,271 when you book by Nov-30-2020**
" This was one of the best large group trips we have ever taken. The place was far better than we expected. Paolo, the owner/architect was a charming guy who was t..." - Richard
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 Nov-30-2020**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
Save $1,204 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $5,880/wk
  • max $12,040/wk
  • min $5,292/wk
  • max $10,836/wk
  • Min Stay: 7 days
Sleeps 29 people
  • 5 single bedrooms
  • 12 double bedrooms
  • 15 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,204 when you book by Nov-30-2020**
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 Nov-30-2020**
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 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Nov-30-2020**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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 Nov-30-2020**
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 Nov-30-2020**
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
** Save up to $196 when you book by Nov-30-2020**
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 Nov-30-2020**
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 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Nov-30-2020**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
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 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Nov-30-2020**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $261 Photo of Tuscan Apartment in Historic Castle
  • min $1,454/wk
  • max $2,611/wk
  • min $1,309/wk
  • max $2,350/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $261 when you book by Nov-30-2020**
" Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
Save $165 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $1,647/wk
  • min $880/wk
  • max $1,482/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $165 when you book by Nov-30-2020**
" Terrific!..." - Ross
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 Nov-30-2020**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
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 Nov-30-2020**
" 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 $127 Photo of Ancient Hamlet in Tuscany near Florence
  • min $931/wk
  • max $1,274/wk
  • min $838/wk
  • max $1,147/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $127 when you book by Nov-30-2020**
 
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..