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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 $5,300/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 $2,580 when you book by Sep-30-2020**
" 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 $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-30-2020**
" 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 Sep-30-2020**
" 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 $108 Photo of Apartment Farmhouse in Tuscany
  • min $925/wk
  • max $1,079/wk
  • min $833/wk
  • max $971/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $108 when you book by Sep-30-2020**
" 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 $532 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,321/wk
  • min $2,206/wk
  • max $4,789/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 $532 when you book by Sep-30-2020**
" Absolutely excellent. ..." - Kerby
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-30-2020**
" 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 $581 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,811/wk
  • min $2,521/wk
  • max $5,230/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 $581 when you book by Sep-30-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,323/wk
  • max $8,663/wk
  • min $3,891/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 $866 when you book by Sep-30-2020**
" 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 $1,582 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,599/wk
  • max $15,820/wk
  • min $10,439/wk
  • max $14,238/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,582 when you book by Sep-30-2020**
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-30-2020**
" 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 $1,633 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,415/wk
  • max $16,328/wk
  • min $8,474/wk
  • max $14,695/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 $1,633 when you book by Sep-30-2020**
Save $237 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,067/wk
  • max $2,372/wk
  • min $960/wk
  • max $2,135/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 $237 when you book by Sep-30-2020**
Save $3,466 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • $34,655/wk
  • $31,190/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,466 when you book by Sep-30-2020**
" The historical impact of the villa made it magical. ..." - Mike
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-30-2020**
" Very nice and restful. S..." - Olenka
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-30-2020**
Save $956 Photo of Chianti Villa near a Charming Village
  • min $1,129/wk
  • max $9,557/wk
  • min $1,016/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-30-2020**
" Great experience in a spectacular villa...." - Viviane
Save $216 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,441/wk
  • max $2,157/wk
  • min $1,297/wk
  • max $1,941/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 Sep-30-2020**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $235 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,672/wk
  • max $2,353/wk
  • min $1,505/wk
  • max $2,118/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $235 when you book by Sep-30-2020**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
Save $137 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,373/wk
  • min $878/wk
  • max $1,236/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $137 when you book by Sep-30-2020**
" It was amazing. Everything was very well done...." - Simin
Save $167 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,168/wk
  • max $1,667/wk
  • min $1,051/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $167 when you book by Sep-30-2020**
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
Save $255 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,549/wk
  • min $1,520/wk
  • max $2,294/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 $255 when you book by Sep-30-2020**
" 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 $226 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,513/wk
  • max $2,255/wk
  • min $1,362/wk
  • max $2,030/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $226 when you book by Sep-30-2020**
" 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 $293 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,945/wk
  • max $2,927/wk
  • min $1,751/wk
  • max $2,634/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 $293 when you book by Sep-30-2020**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
Save $177 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $1,765/wk
  • min $1,123/wk
  • max $1,589/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $177 when you book by Sep-30-2020**
" Wonderful!..." - Peter
Save $296 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,969/wk
  • max $2,955/wk
  • min $1,772/wk
  • max $2,660/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $296 when you book by Sep-30-2020**
" 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 $182 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,280/wk
  • max $1,821/wk
  • min $1,152/wk
  • max $1,639/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $182 when you book by Sep-30-2020**
" Very happy; would go again...." - Karen
Save $2,170 Photo of Luxury Villa Rental Near Siena
  • $21,703/wk
  • $19,533/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 $2,170 when you book by Sep-30-2020**
" The villa was lovely...." - Phyllis
Save $324 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,057/wk
  • max $3,235/wk
  • min $1,851/wk
  • max $2,912/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 $324 when you book by Sep-30-2020**
" 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 $279 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,784/wk
  • max $2,794/wk
  • min $1,606/wk
  • max $2,515/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $279 when you book by Sep-30-2020**
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Save $148 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,105/wk
  • max $1,478/wk
  • min $995/wk
  • max $1,330/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $148 when you book by Sep-30-2020**
" This was a wonderful experience. Ricardo, Sandra and Simona were always helpful and responsive. They helped us work on our Italian language skills with a smile a..." - Ellen
 
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..