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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 101 villas
Save $858 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • $8,575/wk
  • $7,718/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $858 when you book by Jun-20-2019**
" It was very pleasant. Getting there late at night and having a bottle of wine and homemade lasagna, olive oil and bread, was a very welcomed surprise...." - Janice
Save $157 Photo of Family-Friendly Apartment Close to Siena
  • min $1,030/wk
  • max $1,565/wk
  • min $927/wk
  • max $1,409/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Jun-20-2019**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $1,470 Photo of Inviting Tuscan Farmhouse with Incredible Views and Privacy
  • min $9,800/wk
  • max $14,700/wk
  • min $8,820/wk
  • max $13,230/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
** Save up to $1,470 when you book by Jun-20-2019**
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,338/wk
  • max $2,573/wk
  • min $1,204/wk
  • max $2,316/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $257 when you book by Jun-20-2019**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Jun-20-2019**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
Save $1,010 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,758/wk
  • max $10,098/wk
  • min $5,182/wk
  • max $9,088/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,010 when you book by Jun-20-2019**
" Villa Castellina is unbelievably wonderful. It went beyond my wildest imagination. The views were spectacular, modern, comfortable. All of us were so pleased, e..." - Pamela T
Save $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Jun-20-2019**
" Nice small property with charming hosts in a pretty area...." - Sara
Save $1,633 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,415/wk
  • max $16,328/wk
  • min $8,474/wk
  • max $14,695/wk
  • Min Stay: 7 days
Sleeps 14 to 16 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,633 when you book by Jun-20-2019**
Save $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,323/wk
  • max $8,663/wk
  • min $3,891/wk
  • max $7,797/wk
  • Min Stay: 7 days
Sleeps 11 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $866 when you book by Jun-20-2019**
" 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
Save $553 Photo of Villa Rental in Tuscany, Castlenuovo dell'Abate
  • min $3,361/wk
  • max $5,527/wk
  • min $3,025/wk
  • max $4,974/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $553 when you book by Jun-20-2019**
Save $589 Photo of Tuscany Villa with Private Pool
  • min $3,199/wk
  • max $5,887/wk
  • min $2,879/wk
  • max $5,298/wk
  • Min Stay: 7 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
** Save up to $589 when you book by Jun-20-2019**
" 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
Save $181 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,520/wk
  • max $1,814/wk
  • min $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Jun-20-2019**
" Beautiful property, apartment well-appointed. Claudia and Rudi very friendly and helpful finding local eateries, grocery stores. Very quiet and although we were ..." - Susan
Save $1,057 Photo of Tuscany Villa near Siena with Private Pool
  • min $3,338/wk
  • max $7,587/wk
  • min $3,004/wk
  • max $6,828/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,057 when you book by Jun-20-2019**
" Very good. The property management had lots of cheeses, meats, bread and wine for us upon arrival. Both kitchens were well stocked with glassware, dishes, pots an..." - Johnnie Lynn
Save $265 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,224/wk
  • max $2,654/wk
  • min $1,102/wk
  • max $2,389/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $265 when you book by Jun-20-2019**
" Overall, we absolutely loved our stay at this property. It was beautiful, quiet, close to many things that we wanted to see, and a perfect mix of relaxation and b..." - Lisa
Save $205 Photo of Farmhouse Rental in Tuscany, San Giovanni
  • min $1,067/wk
  • max $2,049/wk
  • min $960/wk
  • max $1,844/wk
  • Min Stay: 3 days
Sleeps 2 to 6 people
  • 1 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $205 when you book by Jun-20-2019**
Save $700 Photo of Tuscan Farmhouse with a Private Pool Near Spas
  • min $3,500/wk
  • max $7,000/wk
  • min $3,150/wk
  • max $6,300/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $700 when you book by Jun-20-2019**
" Very nice!..." - Tom
Save $243 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,887/wk
  • max $2,426/wk
  • min $1,698/wk
  • max $2,183/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $243 when you book by Jun-20-2019**
" We had a grand time. The staff were kind and exceedingly helpful. The town was a bit quiet, but we were close to some beautiful towns. ..." - Jamie
Save $210 Photo of Tuscany Villa Rental
  • min $1,470/wk
  • max $2,100/wk
  • min $1,323/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $210 when you book by Jun-20-2019**
" 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
Save $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Jun-20-2019**
" 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
Save $124 Photo of House Rental in Tuscany, Siena
  • min $1,155/wk
  • max $1,239/wk
  • min $1,040/wk
  • max $1,115/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 bathrooms
  • Independent House
  • Maid Service
  • Air Conditioning
** Save up to $124 when you book by Jun-20-2019**
Save $411 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,276/wk
  • max $4,114/wk
  • min $2,048/wk
  • max $3,703/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 $411 when you book by Jun-20-2019**
" The view was great. ..." - Charlotte
Save $414 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,909/wk
  • max $4,142/wk
  • min $1,718/wk
  • max $3,728/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $414 when you book by Jun-20-2019**
" Very nice and restful. S..." - Olenka
Save $1,949 Photo of Villa Rental in Tuscany, Buonconvento
  • min $13,224/wk
  • max $19,488/wk
  • min $11,902/wk
  • max $17,539/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,949 when you book by Jun-20-2019**
Save $1,148 Photo of Large Villa in Tuscany with Two Pools
  • min $9,800/wk
  • max $11,480/wk
  • min $8,820/wk
  • max $10,332/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,148 when you book by Jun-20-2019**
" 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
Save $1,213 Photo of Charming Tuscany Farmhouse Walking Distance to town
  • min $10,782/wk
  • max $12,130/wk
  • min $9,704/wk
  • max $10,917/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
** Save up to $1,213 when you book by Jun-20-2019**
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $588 when you book by Jun-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $305 Photo of Farmhouse Rental in Tuscany, Castellina Scalo
  • min $1,401/wk
  • max $3,046/wk
  • min $1,261/wk
  • max $2,741/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $305 when you book by Jun-20-2019**
" Rosalia 3 is an excellent property if you are looking to spend an authentic week in the Tuscan countryside. Located in a very private setting on a wine estate, th..." - Lisa
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $518 when you book by Jun-20-2019**
" We had a wonderful time at the property..." - Leo
Save $3,851 Photo of Large Estate with Historic Villa and Two Farmhouses for a Large Group
  • min $31,242/wk
  • max $38,505/wk
  • min $28,118/wk
  • max $34,655/wk
  • Min Stay: 3 days
Sleeps 38 people
  • 19 double bedrooms
  • 15 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $3,851 when you book by Jun-20-2019**
" The historical impact of the villa made it magical. ..." - Mike
Save $952 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $3,815/wk
  • max $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 Jun-20-2019**
 
Displaying 31 to 60 of 101 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..