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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 $930 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,300/wk
  • min $4,770/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 Sep-20-2019**
" Villa Dora is an extraordinary villa. Our experience was fantastic in every way...." - Rick
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 Sep-20-2019**
" The property was absolutely beautiful! Maria, the property manager, was wonderful and very accomodating. When we arrived, Maria had a vast arrangement of fruit and..." - Connie
Save $118 Photo of Apartment Farmhouse in Tuscany
  • min $932/wk
  • max $1,177/wk
  • min $839/wk
  • max $1,059/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Sep-20-2019**
" Beautiful property. We enjoyed being on such a lovely property. The apartment was quite comfortable, nothing fancy...." - Kaireen
Save $252 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,762/wk
  • max $2,521/wk
  • min $1,586/wk
  • max $2,269/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $252 when you book by Sep-20-2019**
" Great. Claudia and Rudi terrific ..." - Frank
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 Sep-20-2019**
" Very good...." - Kenneth
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 Sep-20-2019**
" The villa is perched on a hillside with wonderful views and that set the stage for my wife's wish to have friends and family enjoy the Tuscan countryside with ..." - Chris
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/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 $518 when you book by Sep-20-2019**
" Absolutely excellent. ..." - Kerby
Save $123 Photo of Tuscany Vacation Rental Agritourism
  • min $961/wk
  • max $1,230/wk
  • min $865/wk
  • max $1,107/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Sep-20-2019**
" Wonderful...." - Fred
Save $759 Photo of Tuscany Villa near Siena with Private Pool
  • min $3,338/wk
  • max $7,587/wk
  • min $3,004/wk
  • max $6,828/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 $759 when you book by Sep-20-2019**
" 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 $205 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,067/wk
  • max $2,049/wk
  • min $960/wk
  • max $1,844/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 $205 when you book by Sep-20-2019**
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/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 $588 when you book by Sep-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $305 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,401/wk
  • max $3,046/wk
  • min $1,261/wk
  • max $2,741/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $305 when you book by Sep-20-2019**
" 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 $181 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,520/wk
  • max $1,814/wk
  • min $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Sep-20-2019**
" A wonderful place to relax...." - Ruth
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 Sep-20-2019**
Save $3,851 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • max $38,505/wk
  • max $34,655/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,851 when you book by Sep-20-2019**
" The historical impact of the villa made it magical. ..." - Mike
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,338/wk
  • max $2,573/wk
  • min $1,204/wk
  • max $2,316/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $257 when you book by Sep-20-2019**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $414 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,909/wk
  • max $4,142/wk
  • min $1,718/wk
  • max $3,728/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 $414 when you book by Sep-20-2019**
" Very nice and restful. S..." - Olenka
Save $265 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,224/wk
  • max $2,654/wk
  • min $1,102/wk
  • max $2,389/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 $265 when you book by Sep-20-2019**
" 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 $157 Photo of Family-Friendly Apartment Close to Siena
  • min $1,030/wk
  • max $1,565/wk
  • min $927/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 Sep-20-2019**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $1,009 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,746/wk
  • max $10,092/wk
  • min $5,171/wk
  • max $9,083/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,009 when you book by Sep-20-2019**
" 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 $865 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,317/wk
  • max $8,649/wk
  • min $3,885/wk
  • max $7,784/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $865 when you book by Sep-20-2019**
" Terrific! Everything worked, the villa was comfortable and very clean, and it was wonderful to be out in the countryside and simultaneously next to a substantiall..." - Alexander
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 Sep-20-2019**
" Great experience in a spectacular villa...." - Viviane
Save $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,761/wk
  • max $10,092/wk
  • min $5,185/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 Sep-20-2019**
" We had a wonderful, peaceful time...." - Davis
Save $242 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,441/wk
  • max $2,417/wk
  • min $1,297/wk
  • max $2,175/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $242 when you book by Sep-20-2019**
" 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 Sep-20-2019**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
Save $150 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,000/wk
  • max $1,504/wk
  • min $900/wk
  • max $1,354/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $150 when you book by Sep-20-2019**
" Overall, the experience was positive. The apartment and grounds were spotless, exactly the way I like my home in the U.S. The family is very nice, attentive and he..." - Michelle
Save $200 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $2,001/wk
  • min $1,123/wk
  • max $1,801/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $200 when you book by Sep-20-2019**
" Wonderful!..." - Peter
Save $291 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,913/wk
  • min $1,520/wk
  • max $2,622/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 $291 when you book by Sep-20-2019**
" 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 $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 Sep-20-2019**
" 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 $256 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,513/wk
  • max $2,561/wk
  • min $1,362/wk
  • max $2,305/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $256 when you book by Sep-20-2019**
" 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
 
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..