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Italy Accommodations Chianti Tuscany Villa Rentals

Nestled amidst the hills and valleys of the Sienese Chianti-a territory dominated by medieval hill towns---Siena offers a wonderfully preserved example of the Tuscan Middle Ages. The city is home to many Gothic palaces, churches, and museums filled with Gothic art.   Continue >

Displaying 1 to 30 of 82 villas
Save $1,038 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,461/wk
  • max $10,082/wk
  • min $4,423/wk
  • max $9,074/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,038 when you book by Sep-20-2021**
" Excellent LOCATION! ..." - Charles
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-20-2021**
" 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 $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-20-2021**
" 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-20-2021**
" 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 $928 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,515/wk
  • max $9,281/wk
  • min $4,964/wk
  • max $8,353/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $928 when you book by Sep-20-2021**
" We loved this experience! We were there for 2 weeks in August and had different groups of people coming to stay with us. The property is part of a working farm (..." - Marty
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-20-2021**
" 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 $1,405 Photo of Villa Rental in Tuscany, Lucignano d'Asso
  • min $12,433/wk
  • max $14,053/wk
  • min $11,190/wk
  • max $12,648/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,405 when you book by Sep-20-2021**
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-20-2021**
Save $616 Photo of Charming Villa with Pool in Tuscany
  • min $3,676/wk
  • max $6,161/wk
  • min $3,308/wk
  • max $5,545/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 $616 when you book by Sep-20-2021**
" Very Good. A little too far from grocery store and Florence...." - Mary
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-20-2021**
" 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 $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-20-2021**
" 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 $220 Photo of Tuscany Villa Rental
  • min $1,536/wk
  • max $2,196/wk
  • min $1,382/wk
  • max $1,976/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $220 when you book by Sep-20-2021**
" Enjoyed location due to plenty of hiking opportunities with our dog. The property is fine for two people or perhaps a small family. Wouldn't recommend it for t..." - Peter
Save $490 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,801/wk
  • max $4,901/wk
  • min $2,521/wk
  • max $4,411/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $490 when you book by Sep-20-2021**
" The view was great. ..." - Charlotte
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-20-2021**
" 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-20-2021**
" 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 $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-20-2021**
" Very nice and restful. S..." - Olenka
Save $2,007 Photo of Villa Rental in Tuscany, Buonconvento
  • min $12,719/wk
  • max $20,065/wk
  • min $11,447/wk
  • max $18,059/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,007 when you book by Sep-20-2021**
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-20-2021**
Save $813 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,978/wk
  • max $8,134/wk
  • min $6,280/wk
  • max $7,321/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $813 when you book by Sep-20-2021**
Save $402 Photo of House Rental in Tuscany, Buonconvento
  • min $1,876/wk
  • max $4,019/wk
  • min $1,688/wk
  • max $3,617/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $402 when you book by Sep-20-2021**
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-20-2021**
Save $1,112 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $4,575/wk
  • max $11,120/wk
  • min $4,118/wk
  • max $10,008/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,112 when you book by Sep-20-2021**
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-20-2021**
" 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-20-2021**
" 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-20-2021**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
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-20-2021**
" 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-20-2021**
" 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-20-2021**
" 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 $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-20-2021**
" A wonderful place to relax...." - Ruth
  • $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-20-2021**
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
 
Displaying 1 to 30 of 82 villas

Dating back to 1310, the Palio delle Contrade is an annual bareback horse race in which 10 of the city's 17 contrade (neighborhoods) compete. The culminating event of Italy's most spectacular festival, the biggest race is held on August 16; a smaller race is held on July 2nd. In the environs of Radda in Chianti, wine estates such as Castello di Volpaia and Badia a Coltibuono are satisfying side trips for wine and olive oil lovers. Heading northwest of Siena towards San Gimignano, Monteriggioni, one of Italy's most perfectly preserved fortified villages, dominates the vista..