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Chianti Villa Rentals Tuscany, Italy

North of Siena 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 57 villas
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $6,450/wk
  • max $9,900/wk
  • min $5,805/wk
  • max $8,910/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $990 when you book by Jan-20-2022**
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
Save $262 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • $2,615/wk
  • $2,354/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $262 when you book by Jan-20-2022**
" We loved this apt. It is located in the heart of Siena right on Il Campo, the main square and one of the great public spaces of any city in the world. The apt is v..." - Gregory
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $9,522/wk
  • max $12,602/wk
  • min $8,570/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Jan-20-2022**
" It was fantastic. ..." - Jessica
Save $560 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,600/wk
  • max $5,601/wk
  • min $3,240/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $560 when you book by Jan-20-2022**
" We loved the location the restored mill was beautiful, the home decor (mostly antiques were interesting), the internet was highly variable and could have lived for..." - Thomas
Save $248 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,167/wk
  • max $2,480/wk
  • min $1,050/wk
  • max $2,232/wk
  • Min Stay: 3 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $248 when you book by Jan-20-2022**
Save $4,308 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • max $10,098/wk
  • max $9,088/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,308 when you book by Jan-20-2022**
" Villa Castellina is unbelievably wonderful. It went beyond my wildest imagination. The views were spectacular, modern, comfortable. All of us were so pleased, e..." - Pamela T
Save $3,632 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • $36,322/wk
  • $32,690/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,632 when you book by Jan-20-2022**
" The historical impact of the villa made it magical. ..." - Mike
Save $748 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,441/wk
  • max $7,484/wk
  • min $3,097/wk
  • max $6,736/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $748 when you book by Jan-20-2022**
" We were three couples staying at Villa Adelina, and all of us loved our stay. The villa was clean, a bit rustic but very comfortable for our home away from home f..." - Janet
Save $546 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $4,128/wk
  • max $5,463/wk
  • min $3,715/wk
  • max $4,917/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $546 when you book by Jan-20-2022**
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,324/wk
  • max $8,664/wk
  • min $3,892/wk
  • max $7,798/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $866 when you book by Jan-20-2022**
" Terrific! Everything worked, the villa was comfortable and very clean, and it was wonderful to be out in the countryside and simultaneously next to a substantiall..." - Alexander
Save $130 Photo of House Rental in Tuscany, Siena
  • min $1,207/wk
  • max $1,295/wk
  • min $1,086/wk
  • max $1,166/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $130 when you book by Jan-20-2022**
Save $197 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $878/wk
  • max $1,965/wk
  • min $790/wk
  • max $1,769/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $197 when you book by Jan-20-2022**
" When we arrived Maria had wine, fruit, bread, apricot jam (my favourite) and goodies for us (what a lovely touch)! A charcoal BBQ on the patio as you went into th..." - Judy
Save $616 Photo of Charming Villa with Pool in Tuscany
  • min $3,921/wk
  • max $6,161/wk
  • min $3,529/wk
  • max $5,545/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 $616 when you book by Jan-20-2022**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $1,010 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $10,099/wk
  • min $5,198/wk
  • max $9,089/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,010 when you book by Jan-20-2022**
" We had a wonderful, peaceful time...." - Davis
Save $814 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $6,786/wk
  • max $8,144/wk
  • min $6,107/wk
  • max $7,330/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $814 when you book by Jan-20-2022**
" We took this trip to celebrate our 40th anniversary. We were joined by our three adult children and their significant others and our grandson. We had a wonderful..." - Mark
Save $1,633 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,415/wk
  • max $16,328/wk
  • min $8,474/wk
  • max $14,695/wk
  • Min Stay: 7 days
Sleeps 14 to 16 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,633 when you book by Jan-20-2022**
Save $448 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $2,064/wk
  • max $4,480/wk
  • min $1,858/wk
  • max $4,032/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $448 when you book by Jan-20-2022**
" Very nice and restful. S..." - Olenka
Save $1,653 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $12,122/wk
  • max $16,533/wk
  • min $10,910/wk
  • max $14,880/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,653 when you book by Jan-20-2022**
Save $287 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,324/wk
  • max $2,869/wk
  • min $1,192/wk
  • max $2,582/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $287 when you book by Jan-20-2022**
" Overall, we absolutely loved our stay at this property. It was beautiful, quiet, close to many things that we wanted to see, and a perfect mix of relaxation and b..." - Lisa
Save $956 Photo of Chianti Villa near a Charming Village
  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Jan-20-2022**
" Great experience in a spectacular villa...." - Viviane
Save $3,150 Photo of Luxury Villa Rental Near Siena
  • min $28,004/wk
  • max $31,504/wk
  • min $25,204/wk
  • max $28,354/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,150 when you book by Jan-20-2022**
" The villa was lovely...." - Phyllis
Save $614 Photo of Villa Rental in Tuscany, San Gimignano
  • min $4,660/wk
  • max $6,136/wk
  • min $4,194/wk
  • max $5,522/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $614 when you book by Jan-20-2022**
Save $147 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,233/wk
  • max $1,471/wk
  • min $1,110/wk
  • max $1,324/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $147 when you book by Jan-20-2022**
" Our stay greatly facilitated the overall enjoyment of our experience in Tuscany. It is centrally located, and provided easy access to all of the places we wanted ..." - William
Save $301 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,255/wk
  • max $3,011/wk
  • min $2,030/wk
  • max $2,710/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $301 when you book by Jan-20-2022**
" It was an awesome experience. This property has it all. A couple of nights they provide a restaurant dining experience with great ambience. The owners are gracious..." - Charles
Save $1,278 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,622/wk
  • max $12,784/wk
  • min $10,460/wk
  • max $11,506/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,278 when you book by Jan-20-2022**
" The property is beautiful. It seems to have been a hotel at some point so each room has a well appointed bathroom. The kitchen is a commercial kitchen which is v..." - Julia
Save $330 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,515/wk
  • max $3,295/wk
  • min $1,364/wk
  • max $2,966/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $330 when you book by Jan-20-2022**
" We had a wonderful time at Rosalia and in Lilliano. The house was huge and had everything we needed, including a high chair and washing machine, extra blankets. ..." - Holly
Save $108 Photo of Apartment Farmhouse in Tuscany
  • min $925/wk
  • max $1,079/wk
  • min $833/wk
  • max $971/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $108 when you book by Jan-20-2022**
" it exceeded our expectation. Claudia and Rudy were the perfect host, made use feel like family right from the start. invited us to partake in making and cooking re..." - Katheryn
Save $181 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,422/wk
  • max $1,814/wk
  • min $1,280/wk
  • max $1,633/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $181 when you book by Jan-20-2022**
" Wonderful!..." - Peter
Save $2,835 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $21,528/wk
  • max $28,354/wk
  • min $19,375/wk
  • max $25,519/wk
  • Min Stay: 7 days
Sleeps 28 people
  • 14 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $2,835 when you book by Jan-20-2022**
Save $2,441 Photo of Family friendly Tuscan Villa on Wine-Producing Estate
  • min $13,440/wk
  • max $24,413/wk
  • min $12,096/wk
  • max $21,972/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,441 when you book by Jan-20-2022**
" Great place...." - Kathy
 
Displaying 1 to 30 of 57 villas

Following the old Chiantigiana road from your Chianti vacation rental you see the heart of this region, including the Chianti Classico, the Sienese Chianti, and southeast of Siena, the border of Valdarno. To the north lies San Casciano, and further north still, Florence. What to do while staying in one of our villas in 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..