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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 $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 Jan-20-2019**
" Wonderful stay at the property. ..." - Robin
Save $578 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 $578 when you book by Jan-20-2019**
" Beautiful property. We enjoyed being on such a lovely property. The apartment was quite comfortable, nothing fancy...." - Kaireen
Save $459 Photo of Apartment Rental in the Center of Siena
  • min $2,352/wk
  • max $4,587/wk
  • min $2,117/wk
  • max $4,128/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 $459 when you book by Jan-20-2019**
" Very good. The property was well located. ..." - Rick
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 Jan-20-2019**
" Very good...." - Kenneth
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 Jan-20-2019**
" Great. Claudia and Rudi terrific ..." - Frank
Save $1,563 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,012/wk
  • max $15,628/wk
  • min $8,111/wk
  • max $14,065/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 $1,563 when you book by Jan-20-2019**
  • $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 Jan-20-2019**
" the apartment was as advertised and quite comfortable for our needs. It is well situated on the edge of the wall to make parking more convenient and only a couple..." - Linda
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 Jan-20-2019**
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 Jan-20-2019**
" Wonderful...." - Fred
Save $1,285 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,611/wk
  • max $12,850/wk
  • min $10,450/wk
  • max $11,565/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,285 when you book by Jan-20-2019**
Save $2,713 Photo of Luxury Villa Rental Near Siena
  • min $19,603/wk
  • max $27,129/wk
  • min $17,643/wk
  • max $24,416/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 $2,713 when you book by Jan-20-2019**
" The villa was lovely...." - Phyllis
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 Jan-20-2019**
" Our group of ten had a very enjoyable experience at the property...." - Marv
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 Jan-20-2019**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $118 Photo of Tuscany Holiday Apartment
  • 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 Jan-20-2019**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $670 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $2,914/wk
  • max $6,698/wk
  • min $2,623/wk
  • max $6,028/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 $670 when you book by Jan-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 $123 Photo of Farmhouse Accommodation in Tuscany
  • 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 Jan-20-2019**
" Beautiful stay...." - Joan
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 Jan-20-2019**
" It was fantastic. ..." - Jessica
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 Jan-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 $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 Jan-20-2019**
" Beautiful property, apartment well-appointed. Claudia and Rudi very friendly and helpful finding local eateries, grocery stores. Very quiet and although we were ..." - Susan
Save $426 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • max $1,881/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 $426 when you book by Jan-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 $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 Jan-20-2019**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $829 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,138/wk
  • max $8,292/wk
  • min $3,724/wk
  • max $7,463/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 $829 when you book by Jan-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 $967 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,511/wk
  • max $9,665/wk
  • min $4,960/wk
  • max $8,699/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $967 when you book by Jan-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 $299 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,374/wk
  • max $2,987/wk
  • min $1,237/wk
  • max $2,688/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $299 when you book by Jan-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 $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 Jan-20-2019**
" We had a wonderful time at the property..." - Leo
Save $925 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $8,111/wk
  • max $9,245/wk
  • min $7,300/wk
  • max $8,321/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $925 when you book by Jan-20-2019**
" 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 $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 Jan-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 Jan-20-2019**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $406 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,871/wk
  • max $4,061/wk
  • min $1,684/wk
  • max $3,655/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 $406 when you book by Jan-20-2019**
" Very nice and restful. S..." - Olenka
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 Jan-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 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..