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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 Dec-20-2018**
" Wonderful stay at the property. ..." - Robin
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 Dec-20-2018**
" Very good. The property was well located. ..." - Rick
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 Dec-20-2018**
" Beautiful property. We enjoyed being on such a lovely property. The apartment was quite comfortable, nothing fancy...." - Kaireen
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,416/wk
  • max $3,399/wk
  • min $2,174/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 Dec-20-2018**
" Very good...." - Kenneth
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 Dec-20-2018**
" 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
  • $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 Dec-20-2018**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
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 Dec-20-2018**
  • $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 Dec-20-2018**
" 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 $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Dec-20-2018**
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Dec-20-2018**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
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 Dec-20-2018**
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 Dec-20-2018**
" Great. Claudia and Rudi terrific ..." - Frank
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 Dec-20-2018**
Save $967 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,528/wk
  • max $9,665/wk
  • min $4,975/wk
  • max $8,699/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 $967 when you book by Dec-20-2018**
" We had a wonderful, peaceful time...." - Davis
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 Dec-20-2018**
" Wonderful...." - Fred
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 Dec-20-2018**
" The villa was lovely...." - Phyllis
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 Dec-20-2018**
" It was amazing. Everything was very well done...." - Simin
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 Dec-20-2018**
" 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 Dec-20-2018**
" Wonderful!..." - Peter
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 Dec-20-2018**
" Our group of ten had a very enjoyable experience at the property...." - Marv
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 Dec-20-2018**
" Beautiful stay...." - Joan
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 Dec-20-2018**
" 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 Dec-20-2018**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" 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 $144 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $944/wk
  • max $1,441/wk
  • min $850/wk
  • max $1,297/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $144 when you book by Dec-20-2018**
" Perfect!!! Beyond our expectations!!!..." - Rebecca
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,275/wk
  • max $2,573/wk
  • min $1,148/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 Dec-20-2018**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $490 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,186/wk
  • max $4,901/wk
  • min $2,867/wk
  • max $4,411/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 $490 when you book by Dec-20-2018**
" We had a wonderful time at the property..." - Leo
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" Very Good. A little too far from grocery store and Florence...." - Mary
 
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..