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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 56 villas
Save $188 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $840/wk
  • max $1,881/wk
  • min $756/wk
  • max $1,693/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 $188 when you book by Feb-28-2021**
" 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 $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/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 $713 when you book by Feb-28-2021**
" 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 $296 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,157/wk
  • max $2,955/wk
  • min $1,941/wk
  • max $2,660/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $296 when you book by Feb-28-2021**
" It's an amazing property. We had space galore and help when we needed it. The location is very central in Tuscany, so it makes a great home base for daily excu..." - Steven
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 Feb-28-2021**
" Great experience in a spectacular villa...." - Viviane
Save $532 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,221/wk
  • max $5,321/wk
  • min $2,899/wk
  • max $4,789/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 $532 when you book by Feb-28-2021**
" Absolutely excellent. ..." - Kerby
Save $237 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,118/wk
  • max $2,372/wk
  • min $1,006/wk
  • max $2,135/wk
  • Min Stay: 7 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $237 when you book by Feb-28-2021**
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,615/wk
  • max $3,399/wk
  • min $2,354/wk
  • max $3,059/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $340 when you book by Feb-28-2021**
" Very good...." - Kenneth
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,155/wk
  • max $1,239/wk
  • min $1,040/wk
  • max $1,115/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $124 when you book by Feb-28-2021**
Save $1,582 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,599/wk
  • max $15,820/wk
  • min $10,439/wk
  • max $14,238/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,582 when you book by Feb-28-2021**
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,900/wk
  • min $4,770/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 Feb-28-2021**
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
Save $324 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,353/wk
  • max $3,235/wk
  • min $2,118/wk
  • max $2,912/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $324 when you book by Feb-28-2021**
" 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
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 Feb-28-2021**
Save $581 Photo of Charming Villa with Pool in Tuscany
  • min $3,676/wk
  • max $5,811/wk
  • min $3,308/wk
  • max $5,230/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 $581 when you book by Feb-28-2021**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $273 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,261/wk
  • max $2,734/wk
  • min $1,135/wk
  • max $2,461/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 $273 when you book by Feb-28-2021**
" 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 $809 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $7,088/wk
  • max $8,089/wk
  • min $6,379/wk
  • max $7,280/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $809 when you book by Feb-28-2021**
" 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 $427 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,966/wk
  • max $4,267/wk
  • min $1,769/wk
  • max $3,840/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 $427 when you book by Feb-28-2021**
" Very nice and restful. S..." - Olenka
Save $3,632 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • min $36,322/wk
  • max $36,323/wk
  • min $32,690/wk
  • max $32,691/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 Feb-28-2021**
" The historical impact of the villa made it magical. ..." - Mike
Save $314 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,443/wk
  • max $3,137/wk
  • min $1,299/wk
  • max $2,823/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $314 when you book by Feb-28-2021**
" Rosalia 3 is an excellent property if you are looking to spend an authentic week in the Tuscan countryside. Located in a very private setting on a wine estate, th..." - Lisa
Save $293 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,059/wk
  • max $2,927/wk
  • min $1,853/wk
  • max $2,634/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $293 when you book by Feb-28-2021**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
Save $495 Photo of Villa Rental in Tuscany, San Gimignano
  • min $2,705/wk
  • max $4,947/wk
  • min $2,435/wk
  • max $4,452/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $495 when you book by Feb-28-2021**
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 Feb-28-2021**
" 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 $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 Feb-28-2021**
" 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 $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 Feb-28-2021**
" A wonderful place to relax...." - Ruth
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Feb-28-2021**
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
Save $1,010 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $10,098/wk
  • min $5,198/wk
  • max $9,088/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 Feb-28-2021**
" We had a wonderful, peaceful time...." - Davis
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 Feb-28-2021**
" 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 $216 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,520/wk
  • max $2,157/wk
  • min $1,368/wk
  • max $1,941/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $216 when you book by Feb-28-2021**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/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 $713 when you book by Feb-28-2021**
" 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
Save $304 Photo of Apartment Rental in the Center of Siena
  • min $1,960/wk
  • max $3,038/wk
  • min $1,764/wk
  • max $2,734/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $304 when you book by Feb-28-2021**
" Very good. The property was well located. ..." - Rick
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 Feb-28-2021**
" It was fantastic. ..." - Jessica
 
Displaying 1 to 30 of 56 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..