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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 $5,625/wk
  • max $9,900/wk
  • min $5,063/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 Dec-10-2022**
" 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 Dec-10-2022**
" 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 $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 Dec-10-2022**
" The historical impact of the villa made it magical. ..." - Mike
Save $3,501 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $21,528/wk
  • max $35,005/wk
  • min $19,375/wk
  • max $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 Dec-10-2022**
Save $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $10,092/wk
  • min $5,198/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 Dec-10-2022**
" The property itself was very pretty with amazing views. It was centrally located and fairly easy to access. ..." - Jacqueline
  • 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
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
  • 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
Save $123 Photo of Vacation Rental Agritourism in Tuscany
  • $1,233/wk
  • $1,110/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Dec-10-2022**
" 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 $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 Dec-10-2022**
" A wonderful experience at the villa...." - John
  • Enquire for Rates
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
  • 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
  • min $9,415/wk
  • max $12,950/wk
  • min $8,474/wk
  • max $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 Dec-10-2022**
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 Dec-10-2022**
" It was fantastic. ..." - Jessica
  • Enquire for Rates
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
  • $925/wk
  • $833/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $93 when you book by Dec-10-2022**
" 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
  • 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
Save $474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,441/wk
  • max $4,744/wk
  • min $3,097/wk
  • max $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 Dec-10-2022**
" 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 $2,380 Photo of Villa Rental in Tuscany, Casole d'Elsa
  • min $12,613/wk
  • max $23,800/wk
  • min $11,352/wk
  • max $21,420/wk
  • Min Stay: 4 days
Sleeps 30 people
  • 8 single bedrooms
  • 11 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $2,380 when you book by Dec-10-2022**
Save $350 Photo of House Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • $3,501/wk
  • $3,151/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Swimming Pool
** Save up to $350 when you book by Dec-10-2022**
Save $1,680 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • $16,803/wk
  • $15,123/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,680 when you book by Dec-10-2022**
Save $3,638 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • min $22,050/wk
  • max $36,379/wk
  • min $19,845/wk
  • max $32,741/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,638 when you book by Dec-10-2022**
Save $3,372 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • min $16,603/wk
  • max $33,724/wk
  • min $14,943/wk
  • max $30,352/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,372 when you book by Dec-10-2022**
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 Dec-10-2022**
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 Dec-10-2022**
Save $219 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $878/wk
  • max $2,193/wk
  • min $790/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 Dec-10-2022**
" 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
  • $813/wk
  • $732/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $81 when you book by Dec-10-2022**
" Wonderful...." - Fred
Save $344 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • $3,441/wk
  • $3,097/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $344 when you book by Dec-10-2022**
" We thoroughly enjoyed ourselves and were happy with the villa. The location was awesome. We traveled throughout Tuscany and found the villa to be centrally locat..." - Maurice
 
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..