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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 106 villas
  • 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 $1,689/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 $10,782/wk
  • max $12,130/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 $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 $1,441/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
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
  • 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 $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 $1,513/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 $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 $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 $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 $1,168/wk
  • max $1,920/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
  • 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 $1,945/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 $1,248/wk
  • max $2,001/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Wonderful!..." - Peter
  • 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 $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 $1,280/wk
  • max $2,161/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 $1,958/wk
  • max $4,176/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • $4,667/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $8,111/wk
  • max $9,245/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" 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 $4,138/wk
  • max $6,784/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • 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
" The villa was lovely...." - Phyllis
  • 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
Save $1,833 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $14,553/wk
  • max $19,285/wk
  • min $13,098/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
** Save up to $1,833 when you book by Jul-31-2018**
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The size of the bedrooms, bathrooms and the outside patio area...." - Monica
  • min $3,680/wk
  • max $9,184/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • $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
  • $1,371/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
 
Displaying 61 to 90 of 106 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..