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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.   Continue >

Displaying 61 to 90 of 100 villas
  • min $1,000/wk
  • max $1,504/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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 $1,280/wk
  • max $2,081/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very happy; would go again...." - Karen
  • min $1,672/wk
  • max $2,689/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
  • min $1,969/wk
  • max $3,376/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very good...." - Leonard
  • min $1,689/wk
  • max $2,913/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Amazing! We felt like we were part of a family on the property - Sandra, Nicolo, and all the staff were so friendly and helpful. The whole experience made us fee..." - Rayna
  • min $28,117/wk
  • max $31,119/wk
  • Min Stay: 3 days
Sleeps 34 people
  • 17 double bedrooms
  • 14 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The historical impact of the villa made it magical. ..." - Mike
  • min $1,168/wk
  • max $1,849/wk
  • Min Stay: 5 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
  • min $1,945/wk
  • max $3,346/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
  • min $5,528/wk
  • max $9,380/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a wonderful, peaceful time...." - Davis
  • min $2,057/wk
  • max $3,665/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our overall experience was fantastic. We were a group of 6 adults, retirement-aged, and were overwhelmed by the property. It fitted our needs beautifully. It wa..." - Nanci
  • min $1,927/wk
  • max $3,204/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $2,240/wk
  • max $2,800/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The view from the property of the Tuscan Hills was breathtaking. We enjoyed our visits to the small villages and Tuscany area. We felt that we touched the heart ..." - Dixie
  • min $6,237/wk
  • max $9,765/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $2,353/wk
  • max $3,117/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
  • min $1,450/wk
  • max $2,801/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very good. We were upgraded us to a larger unit...." - Donna
  • min $5,755/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • min $4,464/wk
  • max $8,123/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of ten had a very enjoyable experience at the property...." - Marv
  • min $992/wk
  • max $1,706/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
  • min $25,940/wk
  • max $33,961/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
  • min $2,353/wk
  • max $3,117/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • $915/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
" The location was perfect, both in relation to the town, and to the parking...." - Christine
  • min $1,245/wk
  • max $2,307/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The view of the hills, grape orchard, and olive trees...." - Ann
  • min $11,256/wk
  • max $13,221/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very good...." - Bill
  • $915/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
" the apartment was as advertised and quite comfortable for our needs. It is well situated on the edge of the wall to make parking more convenient and only a couple..." - Linda
  • min $14,553/wk
  • max $18,333/wk
  • Min Stay: 7 days
Sleeps 11 to 13 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $1,050/wk
  • max $1,239/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
  • min $18,357/wk
  • max $27,430/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,277/wk
  • max $1,916/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $4,802/wk
  • max $5,782/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $1,903/wk
  • max $3,894/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
 
Displaying 61 to 90 of 100 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. If you are looking for a villa or rental apartment for your romantic honeymoon, or a house with swimming pool for your family vacation, view our Siena Rental Accommodations..