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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 63 villas
Save $930 Photo of Villa on Large Estate Near San Gimignano
  • min $4,500/wk
  • max $9,300/wk
  • min $4,050/wk
  • max $8,370/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $930 when you book by Oct-31-2018**
" It was a wonderful stay. The scenery was stunning, and the owners were very thoughtful and accommodating. We loved all the space, which made it easy for our group ..." - Nicole
Save $1,232 Photo of Apartment Farmhouse in Tuscany
  • min $1,025/wk
  • max $1,295/wk
  • min $820/wk
  • max $1,036/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,232 when you book by Oct-31-2018**
" It was a very nice time. Claudia and Rudi were great and wonderful hosts. Pizza parties were really special times...." - Allen
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 Oct-31-2018**
" The property manager was a gem. The garden was so wonderful. Very inviting place and it was so convenient to go to Siena and so many wineries. One of the best v..." - Harold
Save $748 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,296/wk
  • max $3,739/wk
  • min $1,837/wk
  • max $2,991/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $748 when you book by Oct-31-2018**
" Very good...." - Kenneth
Save $1,474 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,205/wk
  • max $7,368/wk
  • min $2,564/wk
  • max $5,894/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 $1,474 when you book by Oct-31-2018**
" We had a wonderful time at Villa Adelina. The rooms were large and we thought it was great that everyone had their own bathroom. I don't know how it compares..." - Patricia
Save $1,604 Photo of Tuscany Villa near Siena with Private Pool
  • min $2,055/wk
  • max $8,022/wk
  • min $1,644/wk
  • max $6,418/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,604 when you book by Oct-31-2018**
" Very good. The property management had lots of cheeses, meats, bread and wine for us upon arrival. Both kitchens were well stocked with glassware, dishes, pots an..." - Johnnie Lynn
Save $560 Photo of Charming Villa with Pool in Tuscany
  • min $3,641/wk
  • max $5,601/wk
  • min $3,277/wk
  • max $5,041/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 $560 when you book by Oct-31-2018**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $2,240 Photo of Luxury Villa Rental Near Siena
  • min $19,603/wk
  • max $22,403/wk
  • min $17,643/wk
  • max $20,163/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 $2,240 when you book by Oct-31-2018**
" The villa was lovely...." - Phyllis
Save $1,078 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,505/wk
  • max $5,391/wk
  • min $2,804/wk
  • max $4,313/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 $1,078 when you book by Oct-31-2018**
" We had a wonderful time at the property..." - Leo
Save $657 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,511/wk
  • max $3,286/wk
  • min $1,209/wk
  • max $2,629/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $657 when you book by Oct-31-2018**
" 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 $893 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $2,058/wk
  • max $4,467/wk
  • min $1,646/wk
  • max $3,574/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 $893 when you book by Oct-31-2018**
" Very nice and restful. S..." - Olenka
Save $812 Photo of Farmhouse on Historic Estate in the Chianti
  • min $4,464/wk
  • max $8,123/wk
  • min $4,018/wk
  • max $7,311/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 $812 when you book by Oct-31-2018**
" Our group of ten had a very enjoyable experience at the property...." - Marv
Save $157 Photo of Family-Friendly Apartment Close to Siena
  • min $981/wk
  • max $1,565/wk
  • min $883/wk
  • max $1,409/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Oct-31-2018**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $3,438 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,913/wk
  • max $17,191/wk
  • min $7,931/wk
  • max $13,753/wk
  • Min Stay: 7 days
Sleeps 14 to 18 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,438 when you book by Oct-31-2018**
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,050/wk
  • max $1,239/wk
  • min $945/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 Oct-31-2018**
Save $260 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,200/wk
  • max $2,602/wk
  • min $1,080/wk
  • max $2,342/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 $260 when you book by Oct-31-2018**
" 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 $6,846 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • $34,231/wk
  • $27,385/wk
  • Min Stay: 3 days
Sleeps 34 people
  • 17 double bedrooms
  • 14 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $6,846 when you book by Oct-31-2018**
" The historical impact of the villa made it magical. ..." - Mike
Save $641 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,858/wk
  • max $3,204/wk
  • min $1,486/wk
  • max $2,563/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $641 when you book by Oct-31-2018**
" Amazing! We felt like we were part of a family on the property - Sandra, Nicolo, and all the staff were so friendly and helpful. The whole experience made us fee..." - Rayna
Save $566 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,403/wk
  • max $2,830/wk
  • min $1,122/wk
  • max $2,264/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $566 when you book by Oct-31-2018**
" The view of the hills, grape orchard, and olive trees...." - Ann
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 Oct-31-2018**
" Everything was fine...." - William
Save $338 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,969/wk
  • max $3,376/wk
  • min $1,772/wk
  • max $3,038/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $338 when you book by Oct-31-2018**
" Very good...." - Leonard
Save $532 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,585/wk
  • max $2,659/wk
  • min $1,268/wk
  • max $2,127/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $532 when you book by Oct-31-2018**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $269 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,672/wk
  • max $2,689/wk
  • min $1,505/wk
  • max $2,420/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $269 when you book by Oct-31-2018**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
Save $317 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,038/wk
  • max $1,585/wk
  • min $831/wk
  • max $1,268/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $317 when you book by Oct-31-2018**
" It was a wonderful place that deserves recognition...." - Marilyn
Save $147 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,472/wk
  • min $878/wk
  • max $1,325/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $147 when you book by Oct-31-2018**
" It was amazing. Everything was very well done...." - Simin
Save $806 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,263/wk
  • max $4,032/wk
  • min $1,810/wk
  • max $3,225/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $806 when you book by Oct-31-2018**
" Our overall experience was fantastic. We were a group of 6 adults, retirement-aged, and were overwhelmed by the property. It fitted our needs beautifully. It wa..." - Nanci
Save $440 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,373/wk
  • max $2,201/wk
  • min $1,098/wk
  • max $1,761/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $440 when you book by Oct-31-2018**
" Wonderful!..." - Peter
Save $216 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,280/wk
  • max $2,161/wk
  • min $1,152/wk
  • max $1,945/wk
  • Min Stay: 5 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 Oct-31-2018**
" Very happy; would go again...." - Karen
Save $422 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,285/wk
  • max $2,112/wk
  • min $1,028/wk
  • max $1,690/wk
  • Min Stay: 5 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $422 when you book by Oct-31-2018**
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
Save $169 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,105/wk
  • max $1,689/wk
  • min $995/wk
  • max $1,520/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $169 when you book by Oct-31-2018**
" This was a wonderful experience. Ricardo, Sandra and Simona were always helpful and responsive. They helped us work on our Italian language skills with a smile a..." - Ellen
 
Displaying 1 to 30 of 63 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. View our Rental Villas in North Siena..