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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 59 villas
Save $2,580 Photo of Villa on Large Estate Near San Gimignano
  • min $5,653/wk
  • max $9,300/wk
  • min $5,088/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 $2,580 when you book by Apr-10-2020**
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
Save $196 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,513/wk
  • max $1,961/wk
  • min $1,362/wk
  • max $1,765/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $196 when you book by Apr-10-2020**
" Great. Claudia and Rudi terrific ..." - Frank
Save $380 Photo of Apartment Rental in the Center of Siena
  • min $2,450/wk
  • max $3,799/wk
  • min $2,205/wk
  • max $3,419/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 $380 when you book by Apr-10-2020**
" Very good. The property was well located. ..." - Rick
Save $198 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $840/wk
  • max $1,980/wk
  • min $756/wk
  • max $1,782/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 $198 when you book by Apr-10-2020**
" When we arrived Maria had wine, fruit, bread, apricot jam (my favourite) and goodies for us (what a lovely touch)! A charcoal BBQ on the patio as you went into th..." - Judy
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 Apr-10-2020**
" We were three couples staying at Villa Adelina, and all of us loved our stay. The villa was clean, a bit rustic but very comfortable for our home away from home f..." - Janet
Save $1,278 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,622/wk
  • max $12,784/wk
  • min $10,460/wk
  • max $11,506/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,278 when you book by Apr-10-2020**
" The property is beautiful. It seems to have been a hotel at some point so each room has a well appointed bathroom. The kitchen is a commercial kitchen which is v..." - Julia
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 Apr-10-2020**
" Very good...." - Kenneth
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 Apr-10-2020**
" It was fantastic. ..." - Jessica
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 Apr-10-2020**
" Wonderful...." - Fred
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 Apr-10-2020**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $151 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,345/wk
  • max $1,513/wk
  • min $1,211/wk
  • max $1,362/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $151 when you book by Apr-10-2020**
" A wonderful place to relax...." - Ruth
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 Apr-10-2020**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
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 Apr-10-2020**
" Absolutely excellent. ..." - Kerby
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 Apr-10-2020**
" it exceeded our expectation. Claudia and Rudy were the perfect host, made use feel like family right from the start. invited us to partake in making and cooking re..." - Katheryn
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 Apr-10-2020**
" Beautiful stay...." - Joan
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 Apr-10-2020**
" The view of the hills, grape orchard, and olive trees...." - Ann
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 Apr-10-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $713 when you book by Apr-10-2020**
" We thoroughly enjoyed ourselves and were happy with the villa. The location was awesome. We traveled throughout Tuscany and found the villa to be centrally locat..." - Maurice
Save $1,909 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • max $8,663/wk
  • max $7,797/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 $1,909 when you book by Apr-10-2020**
" 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 $367 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,057/wk
  • max $3,665/wk
  • min $1,851/wk
  • max $3,299/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $367 when you book by Apr-10-2020**
" Except for a cooking class at the estate, we spent our time traveling to Siena, Florence, Cinque Terre, and the Chianti region during our 5 night stay. I'd ra..." - Bob
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: 7 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 Apr-10-2020**
" 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 $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: 7 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 Apr-10-2020**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
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: 7 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 Apr-10-2020**
" Wonderful!..." - Peter
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: 7 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 Apr-10-2020**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
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: 7 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 Apr-10-2020**
" It was amazing. Everything was very well done...." - Simin
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 Apr-10-2020**
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: 7 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 Apr-10-2020**
" 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
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: 7 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 Apr-10-2020**
" Very happy; would go again...." - Karen
Save $809 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $7,088/wk
  • max $8,089/wk
  • min $6,379/wk
  • max $7,280/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $809 when you book by Apr-10-2020**
" 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 $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 Apr-10-2020**
" Great experience in a spectacular villa...." - Viviane
 
Displaying 1 to 30 of 59 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..