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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 31 to 60 of 99 villas
  • $1,401/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 $9,800/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 $2,914/wk
  • max $6,698/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" This was our second time at the property...." - Michael
  • min $3,221/wk
  • max $5,321/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" There were three couples/friends sharing the villa. The three bedrooms downstairs were quite nice and all had their space. The owner was lovely. Accommodations for..." - Lee
  • min $3,500/wk
  • max $7,000/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" It was everything we hoped for and more. Everything was top notch, from the location to the amenities. Since we rented both apartments, it was very private...." - Norma
  • min $3,186/wk
  • max $4,901/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful time at the property..." - Leo
  • $1,401/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
  • $1,681/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Owners were great. Nice people. Very informative. Property was very nice in good locations to go leave from for day trips...." - William
  • 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
  • $1,401/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
" 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 $2,440/wk
  • max $4,100/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" A beautiful place, close to town. Very pleasant gardens...." - Cherise
  • min $3,641/wk
  • max $5,601/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Our group of six people - three couples - were delighted with the experience of sharing this beautiful villa for a week. ..." - Joan
  • min $1,955/wk
  • max $3,609/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
" The view was great. ..." - Charlotte
  • min $1,871/wk
  • max $4,061/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Extremely relaxing and enjoyable stay...." - Everett
  • min $1,374/wk
  • max $2,987/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" We had a wonderful time. Yolanda is a sweetheart. Very accommodating and whatever issues we had, she handled them immediately and in a courteous manner. She ma..." - Jan
  • $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 $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 $1,470/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 $6,371/wk
  • max $11,272/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Everything was fine...." - William
  • min $4,138/wk
  • max $8,292/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 $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 $1,784/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 $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 $1,200/wk
  • max $2,602/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" The property was very nice. ..." - Suzanna
  • min $9,012/wk
  • max $15,628/wk
  • Min Stay: 7 days
Sleeps 14 to 18 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • 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
  • 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 $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 $10,500/wk
  • max $12,460/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Our expectations were exceeded. We rented the villa for the month of October 2015. The property manager, is a master of customer service and charm...." - Alice
  • 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
 
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. 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..