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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 62 villas
  • min $932/wk
  • max $1,177/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Fantastic!!! This was our 4th time to return! Loved it and love Claudia, Rudi and Simone!..." - Dana
  • min $1,200/wk
  • max $9,300/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The caretaker was fantastic upon our arrival! He provided an excellent tour and answered all of our questions. The villa exceeded my expectations and I have alre..." - Brandi
  • min $2,087/wk
  • max $2,416/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
" Very good...." - Kenneth
  • min $5,951/wk
  • max $7,186/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful experience at this property. It was a perfect location close to Siena. ..." - Pennie
  • min $4,464/wk
  • max $8,123/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of ten had a very enjoyable experience at the property...." - Marv
  • min $1,245/wk
  • max $2,307/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Overall the property and atmosphere were great. The location was convenient to Siena and we found this to be very enjoyable, much more so than Florence...." - Peter
  • min $3,890/wk
  • max $6,125/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Casa Luciana was perfect for the four couple who stayed there. It was a gorgeous place and actually had 6 bedrooms and 7 bathrooms. Loved it!! ..." - Nancy
  • min $8,629/wk
  • max $10,935/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" I would and already have recommended the villa to anyone. My experience with your firm was excellent. When I return to Tuscany I intend to stay at the same locatio..." - Hal
  • min $932/wk
  • max $1,177/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
  • min $1,868/wk
  • max $7,293/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
" 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
  • min $11,611/wk
  • max $12,850/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $7,473/wk
  • max $8,831/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Beautiful stay...." - Joan
  • min $19,603/wk
  • max $22,403/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Excellent..." - Carmel
  • min $1,520/wk
  • max $1,814/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Wonderful...awesome!! It was so peaceful and relaxing, just what we needed! The hosts were very welcoming, friendly and helpful they gave us additional information..." - Anita
  • min $9,522/wk
  • max $12,602/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Good...." - Jim
  • min $5,511/wk
  • max $9,665/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $1,762/wk
  • max $2,521/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was everything I had hoped for. We enjoyed the other guests and our privacy on the spacious grounds...." - Robert
  • min $840/wk
  • max $1,881/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
  • min $2,352/wk
  • max $3,528/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $961/wk
  • max $1,230/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" This was my second visit in five months! I love it!..." - Barbara
  • min $3,186/wk
  • max $4,901/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful time at the property..." - Leo
  • min $3,641/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of six people - three couples - were delighted with the experience of sharing this beautiful villa for a week. ..." - Joan
  • min $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This was our second time at the property...." - Michael
  • min $1,871/wk
  • max $4,061/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Extremely relaxing and enjoyable stay...." - Everett
  • min $1,374/wk
  • max $2,987/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We had a wonderful time. Yolanda is a sweetheart. Very accommodating and whatever issues we had, she handled them immediately and in a courteous manner. She ma..." - Jan
  • min $1,441/wk
  • max $2,417/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful experience! The staff was amazing! The property was gorgeous and the dinners were unforgettable! ..." - Tess
  • min $1,513/wk
  • max $2,561/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This property is excellent. The owners are the most wonderful people. They were always gracious, helpful and friendly. We had a two bedroom apartment with a rea..." - Julie
  • min $1,784/wk
  • max $3,184/wk
  • Min Stay: 5 days
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
 
Displaying 1 to 30 of 62 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..