Siena Villas and Vacation 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 31 to 60 of 99 villas
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 Aug-31-2019**
"
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
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 Aug-31-2019**
"
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 $9,156/wkmax $13,673/wk- min $8,240/wk
- max $12,306/wk
- Min Stay: 7 days
Sleeps 12 people
- 7 double bedrooms
- 6 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
Air Conditioning
** Save up to $1,367 when you book by Aug-31-2019**
min $13,224/wkmax $19,488/wk- min $11,902/wk
- max $17,539/wk
- Min Stay: 7 days
Sleeps 18 people
- 9 double bedrooms
- 9 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,949 when you book by Aug-31-2019**
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 Aug-31-2019**
"
Very nice and restful. S..." - Olenka
min $1,030/wkmax $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 Aug-31-2019**
"
The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
min $1,618/wkmax $2,022/wk- min $1,456/wk
- max $1,820/wk
- Min Stay: 3 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Maid Service
- Air Conditioning
** Save up to $202 when you book by Aug-31-2019**
"
Excellent. In this unit were my wife's mom and our 11 year old twins. They spent more time in the facility while we went out sightseeing more. They loved the a..." - Curtis
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 Aug-31-2019**
min $31,242/wkmax $38,505/wk- min $28,118/wk
- max $34,655/wk
- Min Stay: 3 days
Sleeps 38 people
- 19 double bedrooms
- 15 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $3,851 when you book by Aug-31-2019**
"
The historical impact of the villa made it magical. ..." - Mike
min $1,000/wkmax $1,504/wk- min $900/wk
- max $1,354/wk
- Min Stay: 5 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $150 when you book by Aug-31-2019**
"
Overall, the experience was positive. The apartment and grounds were spotless, exactly the way I like my home in the U.S. The family is very nice, attentive and he..." - Michelle
min $1,784/wkmax $3,184/wk- min $1,606/wk
- max $2,866/wk
- Min Stay: 5 days
Sleeps 4 people
- 2 double bedrooms
- 2 bathrooms
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $318 when you book by Aug-31-2019**
"
We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Displaying 31 to 60 of 99 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..