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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 58 villas
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $8,300/wk
  • max $9,900/wk
  • min $7,470/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 Jun-10-2023**
" Fantastic - Sandro and Nelson were excellent hosts...." - Peggy
  • Enquire for Rates
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
" 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 $3,501 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • $35,005/wk
  • $31,505/wk
  • Min Stay: 7 days
Sleeps 28 people
  • 14 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $3,501 when you book by Jun-10-2023**
  • Enquire for Rates
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The historical impact of the villa made it magical. ..." - Mike
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Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
Save $1,010 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,758/wk
  • max $10,098/wk
  • min $5,182/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 $1,010 when you book by Jun-10-2023**
" A wonderful experience at the villa...." - John
  • Enquire for Rates
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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 $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $6,483/wk
  • max $10,092/wk
  • min $5,835/wk
  • max $9,083/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 $1,009 when you book by Jun-10-2023**
" The property itself was very pretty with amazing views. It was centrally located and fairly easy to access. ..." - Jacqueline
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
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Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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 $474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • $4,744/wk
  • $4,270/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 $474 when you book by Jun-10-2023**
" 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
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Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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 $219 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $1,469/wk
  • max $2,193/wk
  • min $1,322/wk
  • max $1,974/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 $219 when you book by Jun-10-2023**
" 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
  • Enquire for Rates
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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
  • Enquire for Rates
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
  • Enquire for Rates
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $11,342/wk
  • max $12,602/wk
  • min $10,208/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 Jun-10-2023**
" It was fantastic. ..." - Jessica
  • Enquire for Rates
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The villa was lovely...." - Phyllis
Save $1,295 Photo of Large Villa with Pool and Guest House in Chianti
  • $12,950/wk
  • $11,655/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 $1,295 when you book by Jun-10-2023**
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Except for a cooking class at the estate, we spent our time traveling to Siena, Florence, Cinque Terre, and the Chianti region during our 5 night stay. I'd ra..." - Bob
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Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Save $956 Photo of Chianti Villa near a Charming Village
  • $9,557/wk
  • $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 Jun-10-2023**
" Great experience in a spectacular villa...." - Viviane
  • Enquire for Rates
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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
  • Enquire for Rates
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Very nice and restful. S..." - Olenka
  • Enquire for Rates
Sleeps 2 to 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
" The location was perfect, both in relation to the town, and to the parking...." - Christine
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
  • Enquire for Rates
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
 
Displaying 1 to 30 of 58 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..