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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
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 Aug-31-2019**
" Nice small property with charming hosts in a pretty area...." - Sara
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 Aug-31-2019**
" 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 $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 Aug-31-2019**
" 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 $866 Photo of Farmhouse in the Chianti Region for Friends or a Large Family
  • min $4,317/wk
  • max $8,663/wk
  • min $3,885/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 Aug-31-2019**
" 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 $1,367 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
  • min $9,156/wk
  • max $13,673/wk
  • min $8,240/wk
  • max $12,306/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,367 when you book by Aug-31-2019**
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 Aug-31-2019**
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 Aug-24-2019**
" 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 $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 Aug-31-2019**
" Very nice and restful. S..." - Olenka
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 Aug-31-2019**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $300 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $2,157/wk
  • max $3,002/wk
  • min $1,941/wk
  • max $2,702/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $300 when you book by Aug-31-2019**
" We had a very relaxing and enjoyable time at Casa dei Venti - La Tempesta. Our host, Filippo, was very kind and generous and helped us with several outings in the ..." - Jim
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 Aug-31-2019**
" Absolutely excellent. ..." - Kerby
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 Aug-31-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $2,372 Photo of Large Farmhouse on a Wine Estate near Siena Fit for Families
  • min $5,747/wk
  • max $10,092/wk
  • min $5,172/wk
  • max $7,720/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $2,372 when you book by Aug-31-2019**
" 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
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Aug-31-2019**
" 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 Aug-31-2019**
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 Aug-31-2019**
" The historical impact of the villa made it magical. ..." - Mike
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 Aug-31-2019**
" 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 Aug-31-2019**
Save $956 Photo of Chianti Villa near a Charming Village
  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Aug-31-2019**
" Great experience in a spectacular villa...." - Viviane
Save $1,009 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,761/wk
  • max $10,092/wk
  • min $5,185/wk
  • max $9,083/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,009 when you book by Aug-31-2019**
" We had a wonderful, peaceful time...." - Davis
Save $269 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,672/wk
  • max $2,689/wk
  • min $1,505/wk
  • max $2,420/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $269 when you book by Aug-31-2019**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
Save $242 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,441/wk
  • max $2,417/wk
  • min $1,297/wk
  • max $2,175/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $242 when you book by Aug-31-2019**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $200 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $2,001/wk
  • min $1,123/wk
  • max $1,801/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $200 when you book by Aug-31-2019**
" Wonderful!..." - Peter
Save $546 Photo of Enchanting Tuscan Villa Near Montepulciano
  • min $3,361/wk
  • max $5,461/wk
  • min $3,025/wk
  • max $4,915/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $546 when you book by Aug-31-2019**
" Excellent. Villa was very clean and owners were very helpful...." - Gary
Save $291 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,913/wk
  • min $1,520/wk
  • max $2,622/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $291 when you book by Aug-31-2019**
" 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
Save $147 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,472/wk
  • min $878/wk
  • max $1,325/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $147 when you book by Aug-31-2019**
" It was amazing. Everything was very well done...." - Simin
Save $150 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,000/wk
  • max $1,504/wk
  • min $900/wk
  • max $1,354/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $150 when you book by Aug-31-2019**
" 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
Save $318 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,784/wk
  • max $3,184/wk
  • min $1,606/wk
  • max $2,866/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $318 when you book by Aug-31-2019**
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Save $256 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,513/wk
  • max $2,561/wk
  • min $1,362/wk
  • max $2,305/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $256 when you book by Aug-31-2019**
" 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
Save $338 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,969/wk
  • max $3,376/wk
  • min $1,772/wk
  • max $3,038/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $338 when you book by Aug-31-2019**
" It's an amazing property. We had space galore and help when we needed it. The location is very central in Tuscany, so it makes a great home base for daily excu..." - Steven
 
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..