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Siena Villas, Siena Apartments

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 >

Showing 31 to 60 of 97 properties
  • min $1,219/wk
  • max $1,625/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Nice small property with charming hosts in a pretty area...." - Sara
  • min $6,021/wk
  • max $8,402/wk
  • Min Stay: 7 days
Sleeps 12 to 20 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $3,360/wk
  • max $4,667/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" My visit to Italy was spectacular in part due to Villa Seggiano. The location and view were beautiful and the villa impeccably decorated. We had everything we ne..." - Susan
  • min $5,881/wk
  • max $12,000/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $1,219/wk
  • max $1,625/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
" From the time we arrived we were made to feel like family by Filippo and Rachel. The experience was just what we were looking for. A little piece of heaven in the ..." - Brad
  • min $1,470/wk
  • max $2,100/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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 $19,603/wk
  • max $22,403/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Excellent..." - Carmel
  • min $4,569/wk
  • max $9,021/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • min $4,637/wk
  • max $14,700/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • 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 $1,105/wk
  • max $1,689/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This was a wonderful experience. Ricardo, Sandra and Simona were always helpful and responsive. They helped us work on our Italian language skills with a smile a..." - Ellen
Save $372 Photo of Farmhouse in Southern Tuscany with Pool
  • min $1,862/wk
  • max $3,609/wk
  • min $1,490/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 $372 when you book by Oct-31-2017**
" The overall experience was great. We used the villa for a group of 6, and it worked out perfectly...." - Jeffrey
  • min $976/wk
  • max $1,472/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was amazing. Everything was very well done...." - Simin
  • min $1,784/wk
  • max $3,184/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
  • min $6,044/wk
  • max $6,759/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Terrific! It is a very lovely villa - the online pictures don't do it justice. All the charm of an historic villa plus recent renovations that resulted in st..." - Jeanne
  • min $1,248/wk
  • max $1,968/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Wonderful!..." - Peter
  • 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 $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 $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 $944/wk
  • max $1,441/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was a wonderful place that deserves recognition...." - Marilyn
  • min $1,441/wk
  • max $2,417/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful experience! The staff was amazing! The property was gorgeous and the dinners were unforgettable! ..." - Tess
  • 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 $1,672/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 $1,513/wk
  • max $2,561/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This property is excellent. The owners are the most wonderful people. They were always gracious, helpful and friendly. We had a two bedroom apartment with a rea..." - Julie
  • 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 $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 $3,199/wk
  • max $5,887/wk
  • Min Stay: 7 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
" We had a great experience. The owner, Antonella, was exceptionally helpful in so many ways. The property is lovely, and a great deal of thought has been given to..." - Felice
  • min $6,041/wk
  • max $9,371/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • min $3,072/wk
  • max $10,124/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" As a group of 10 friends and neighbors, we really enjoyed all the space, both inside and out, to be together or to have privacy. Loved cooking together and comfor..." - Penelope
 
Showing 31 to 60 of 97 properties

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..