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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 $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 Mar-10-2021**
" 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 $3,016/wk
  • max $3,662/wk
  • min $2,714/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 Mar-10-2021**
" 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 $1,275 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,554/wk
  • min $1,739/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 $1,275 when you book by Mar-10-2021**
" 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 $345 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $2,801/wk
  • max $3,448/wk
  • min $2,521/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 Mar-10-2021**
" 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 $3,448/wk
  • max $4,093/wk
  • min $3,103/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 Mar-10-2021**
" Wonderful all around!..." - Cinnamon
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 Mar-10-2021**
" Wonderful..." - Aline
Save $347 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,440/wk
  • max $3,467/wk
  • min $2,196/wk
  • max $3,120/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 $347 when you book by Mar-10-2021**
" 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 $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 Mar-10-2021**
" 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 $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 Mar-10-2021**
" It was wonderful. ..." - Cathie
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 Mar-10-2021**
" 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 $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 Mar-10-2021**
" Casa Donnini was absolutely wonderful. Great location. Pool. Store, bakery, butcher literally seconds away! A dream come true...." - Mark
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 Mar-10-2021**
" 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 $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 Mar-10-2021**
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 Mar-10-2021**
" Our stay was the highlight of our trip to Italy. ..." - Patty
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 Mar-10-2021**
" Fantastic. 13 adults. Accommodations outstanding and the view is idyllic...." - Joan
Save $165 Photo of Tuscan Apartment in Historic Castle
  • min $884/wk
  • max $1,647/wk
  • min $796/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 Mar-10-2021**
" Terrific!..." - Ross
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 Mar-10-2021**
" 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 $588 Photo of Charming, traditional Tuscan villa with pool, terrace with views, located in Montaione
  • $5,876/wk
  • $5,288/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $588 when you book by Mar-10-2021**
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 Mar-10-2021**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
Save $1,050 Photo of Self Catering Accommodation in Tuscany
  • min $6,721/wk
  • max $10,502/wk
  • min $6,049/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,050 when you book by Mar-10-2021**
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
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 Mar-10-2021**
" Wonderful!..." - Chuck
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: 7 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 Mar-10-2021**
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: 7 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 Mar-10-2021**
Save $1,386 Photo of Beautiful Tuscan Villa on a Large Estate
  • min $5,880/wk
  • max $13,860/wk
  • min $5,292/wk
  • max $12,474/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,386 when you book by Mar-10-2021**
" Wonderful...." - Naomi
Save $182 Photo of Apartment Rental in Tuscany, Tavarnelle in val di Pesa
  • min $1,092/wk
  • max $1,820/wk
  • min $983/wk
  • max $1,638/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $182 when you book by Mar-10-2021**
" It is difficult to find the appropriate words to express how wonderful our experience at Casa della Fioraia was. The view we awoke to every day was spectacular. ..." - Bill
Save $221 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,205/wk
  • min $1,361/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Mar-10-2021**
" We had a great time at Poggio 2. Giulia was very helpful ..." - Karyn
Save $289 Photo of Ancient Hamlet in Tuscany near Florence
  • min $2,107/wk
  • max $2,891/wk
  • min $1,896/wk
  • max $2,602/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $289 when you book by Mar-10-2021**
" Luigi and his staff were great. Friendly and responsive...." - John
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: 7 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 Mar-10-2021**
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 Mar-10-2021**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
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 Mar-10-2021**
" The view and being in a small town. ..." - Joseph
 
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..