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 61 to 90 of 99 villas
min $1,280/wkmax $2,161/wk- min $1,152/wk
- max $1,945/wk
- Min Stay: 5 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 Aug-31-2019**
"
Very happy; would go again...." - Karen
min $8,110/wkmax $9,245/wk- min $7,299/wk
- max $8,321/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 6 bathrooms
Independent House- Swimming Pool
- Washing Machine
** Save up to $925 when you book by Aug-31-2019**
"
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
min $3,815/wkmax $9,520/wk- min $3,434/wk
- max $8,568/wk
- Min Stay: 7 days
Sleeps 8 people
- 4 double bedrooms
- 4 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $952 when you book by Aug-31-2019**
Save $169
min $2,615/wkmax $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 Aug-31-2019**
"
Very good...." - Kenneth
min $2,842/wkmax $4,116/wk- min $2,558/wk
- max $3,704/wk
- Min Stay: 3 days
Sleeps 5 people
- 1 single bedrooms
- 2 double bedrooms
- 2 bathrooms
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $412 when you book by Aug-31-2019**
"
Very good. The property was well located. ..." - Rick
min $932/wkmax $1,177/wk- min $839/wk
- max $1,059/wk
- Min Stay: 4 days
Sleeps 2 to 4 people
- 1 double bedrooms
- 1 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $118 when you book by Aug-31-2019**
"
Absolutely wonderful.
Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
$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 Aug-31-2019**
"
The location was perfect, both in relation to the town, and to the parking...." - Christine
min $2,352/wkmax $3,411/wk- min $2,117/wk
- max $3,070/wk
- Min Stay: 3 days
Sleeps 4 people
- 2 double bedrooms
- 1 bathrooms
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $341 when you book by Aug-31-2019**
"
We had a great time. The property was in excellent condition. Anthony received us well and explained everything we needed and answered all of our questions. ..." - Andy
min $11,611/wkmax $14,877/wk- min $10,450/wk
- max $13,389/wk
- Min Stay: 3 days
Sleeps 18 people
- 9 double bedrooms
- 10 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $1,488 when you book by Aug-31-2019**
min $1,452/wkmax $2,645/wk- min $1,307/wk
- max $2,381/wk
- Min Stay: 7 days
Sleeps 6 to 7 people
- 3 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $265 when you book by Aug-31-2019**
"
Very good. We were upgraded us to a larger unit...." - Donna
min $3,360/wkmax $4,667/wk- min $3,024/wk
- max $4,200/wk
- Min Stay: 7 days
Sleeps 6 people
- 3 double bedrooms
- 2 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
** Save up to $467 when you book by Aug-31-2019**
"
It was like our own villa. The owners were so helpful in making everything work and we enjoyed our holiday.
The sun room was a special place. We set it up as o..." - Geoff
min $915/wkmax $1,121/wk- min $824/wk
- max $1,009/wk
- Min Stay: 3 days
Sleeps 2 people
- 1 double bedrooms
- 1 bathrooms
- Washing Machine
** Save up to $112 when you book by Aug-31-2019**
"
The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
$21,198/wk- $19,078/wk
- Min Stay: 7 days
Sleeps 10 people
- 5 double bedrooms
- 5 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Air Conditioning
** Save up to $2,120 when you book by Aug-31-2019**
min $5,822/wkmax $7,822/wk- min $5,240/wk
- max $7,040/wk
- Min Stay: 5 days
Sleeps 14 people
- 7 double bedrooms
- 5 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
- Air Conditioning
** Save up to $782 when you book by Aug-31-2019**
min $2,353/wkmax $3,117/wk- min $2,118/wk
- max $2,805/wk
- Min Stay: 5 days
Sleeps 6 people
- 3 double bedrooms
- 2 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $312 when you book by Aug-31-2019**
min $1,616/wkmax $3,088/wk- min $1,454/wk
- max $2,779/wk
- Min Stay: 7 days
Sleeps 8 people
- 4 double bedrooms
- 3 bathrooms
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $309 when you book by Aug-31-2019**
"
The size of the bedrooms, bathrooms and the outside patio area...." - Monica
min $13,818/wkmax $16,149/wk- min $12,436/wk
- max $14,534/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 5 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
** Save up to $1,615 when you book by Aug-31-2019**
min $1,042/wkmax $5,353/wk- min $938/wk
- max $4,818/wk
- Min Stay: 7 days
Sleeps 14 people
- 7 double bedrooms
- 7 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
** Save up to $535 when you book by Aug-31-2019**
min $1,042/wkmax $5,353/wk- min $938/wk
- max $4,818/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 6 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
** Save up to $535 when you book by Aug-31-2019**
min $5,880/wkmax $9,016/wk- min $5,292/wk
- max $8,114/wk
- Min Stay: 7 days
Sleeps 12 people
- 6 double bedrooms
- 5 bathrooms
- Independent House
- Swimming Pool
- Washing Machine
- Maid Service
** Save up to $902 when you book by Aug-31-2019**
Displaying 61 to 90 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..