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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 55 villas
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-30-2021**
" Great experience in a spectacular villa...." - Viviane
Save $197 Photo of Country Villa in heart of Chianti centrally located close to regions’ history, art, restaurants.
  • min $878/wk
  • max $1,965/wk
  • min $790/wk
  • max $1,769/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 $197 when you book by Sep-30-2021**
" 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 $1,653 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $12,122/wk
  • max $16,533/wk
  • min $10,910/wk
  • max $14,880/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,653 when you book by Sep-30-2021**
Save $448 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,966/wk
  • max $4,480/wk
  • min $1,769/wk
  • max $4,032/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 $448 when you book by Sep-30-2021**
" Very nice and restful. S..." - Olenka
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,323/wk
  • max $8,664/wk
  • min $3,891/wk
  • max $7,798/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-30-2021**
" 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 $759 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $7,088/wk
  • max $7,594/wk
  • min $6,379/wk
  • max $6,835/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $759 when you book by Sep-30-2021**
" 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 $287 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,261/wk
  • max $2,869/wk
  • min $1,135/wk
  • max $2,582/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 $287 when you book by Sep-30-2021**
" 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 $330 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,443/wk
  • max $3,295/wk
  • min $1,299/wk
  • max $2,966/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $330 when you book by Sep-30-2021**
" 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 $130 Photo of House Rental in Tuscany, Siena
  • min $1,207/wk
  • max $1,295/wk
  • min $1,086/wk
  • max $1,166/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $130 when you book by Sep-30-2021**
Save $990 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,900/wk
  • min $4,770/wk
  • max $8,910/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $990 when you book by Sep-30-2021**
" We absolutely LOVED our stay at Villa Dora! Every room was stunning, and the villa beautifully appointed. Every detail was perfect. The views, and outdoor spaces w..." - Patti
Save $393 Photo of Villa Rental in Tuscany, San Gimignano
  • min $2,705/wk
  • max $3,933/wk
  • min $2,435/wk
  • max $3,540/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $393 when you book by Sep-30-2021**
Save $324 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,353/wk
  • max $3,235/wk
  • min $2,118/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-30-2021**
" 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 $296 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,157/wk
  • max $2,955/wk
  • min $1,941/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-30-2021**
" 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 $293 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,059/wk
  • max $2,927/wk
  • min $1,853/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-30-2021**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
Save $560 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,221/wk
  • max $5,601/wk
  • min $2,899/wk
  • max $5,041/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 $560 when you book by Sep-30-2021**
" We loved the location the restored mill was beautiful, the home decor (mostly antiques were interesting), the internet was highly variable and could have lived for..." - Thomas
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 Sep-30-2021**
" 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 $748 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,484/wk
  • min $2,949/wk
  • max $6,736/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 $748 when you book by Sep-30-2021**
" 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-30-2021**
" 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 $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-30-2021**
" We loved this apt. It is located in the heart of Siena right on Il Campo, the main square and one of the great public spaces of any city in the world. The apt is v..." - Gregory
  • $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 Sep-30-2021**
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
Save $147 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,233/wk
  • max $1,471/wk
  • min $1,110/wk
  • max $1,324/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $147 when you book by Sep-30-2021**
" A wonderful place to relax...." - Ruth
Save $248 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,167/wk
  • max $2,480/wk
  • min $1,050/wk
  • max $2,232/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 $248 when you book by Sep-30-2021**
Save $210 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,401/wk
  • max $2,101/wk
  • min $1,261/wk
  • max $1,891/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Sep-30-2021**
" Great. Claudia and Rudi terrific ..." - Frank
Save $535 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $4,043/wk
  • max $5,352/wk
  • min $3,639/wk
  • max $4,817/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $535 when you book by Sep-30-2021**
Save $108 Photo of Tuscany Holiday Apartment
  • 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-30-2021**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
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 Sep-30-2021**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
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-30-2021**
" The villa was lovely...." - Phyllis
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-30-2021**
Save $721 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $7,210/wk
  • min $5,198/wk
  • max $6,489/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 $721 when you book by Sep-30-2021**
" We had a wonderful, peaceful time...." - Davis
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Sep-30-2021**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
 
Displaying 1 to 30 of 55 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..