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.
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Displaying 1 to 30 of 92 villas
min $1,224/wkmax $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
min $925/wkmax $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
min $925/wkmax $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**
"
Absolutely wonderful.
Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
min $11,599/wkmax $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**
min $1,470/wkmax $2,100/wk- min $1,323/wk
- max $1,890/wk
- Min Stay: 7 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
** Save up to $210 when you book by Sep-30-2020**
"
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
$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
min $1,067/wkmax $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**
min $1,401/wkmax $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
min $1,909/wkmax $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
min $1,155/wkmax $1,239/wk- min $1,040/wk
- max $1,115/wk
- Min Stay: 7 days
- Independent House
- Maid Service
- Air Conditioning
** Save up to $124 when you book by Sep-30-2020**
min $30,874/wkmax $48,516/wk- min $27,787/wk
- max $43,664/wk
- Min Stay: 4 days
Sleeps 24 people
- 12 double bedrooms
- 12 bathrooms
- Independent House
- Swimming Pool
- Air Conditioning
** Save up to $4,852 when you book by Sep-30-2020**
min $1,881/wkmax $4,013/wk- min $1,693/wk
- max $3,612/wk
- Min Stay: 7 days
Sleeps 4 to 6 people
- 2 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $401 when you book by Sep-30-2020**
min $10,086/wkmax $17,651/wk- min $9,077/wk
- max $15,886/wk
- Min Stay: 7 days
Sleeps 18 people
- 9 double bedrooms
- 9 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,765 when you book by Sep-30-2020**
min $5,228/wkmax $11,506/wk- min $4,705/wk
- max $10,355/wk
- Min Stay: 7 days
Sleeps 8 people
- 4 double bedrooms
- 4 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,151 when you book by Sep-30-2020**
Displaying 1 to 30 of 92 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..