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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 92 villas
Save $1,582 Photo of Villa Rental in Tuscany, Castelnuova Berardenga
  • min $11,599/wk
  • max $15,820/wk
  • min $10,439/wk
  • max $14,238/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $1,582 when you book by Jul-10-2020**
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 Jul-10-2020**
" Very nice!..." - Tom
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $9,522/wk
  • max $12,602/wk
  • min $8,570/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Jul-10-2020**
" It was fantastic. ..." - Jessica
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Jul-10-2020**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Jul-10-2020**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
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 Jul-10-2020**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $265 Photo of Family-Friendly Apartment Close to Siena
  • min $1,452/wk
  • max $2,645/wk
  • min $1,307/wk
  • max $2,381/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $265 when you book by Jul-10-2020**
" Very good. We were upgraded us to a larger unit...." - Donna
Save $962 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • $9,615/wk
  • $8,654/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $962 when you book by Jul-10-2020**
" 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 $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $713 when you book by Jul-10-2020**
" We thoroughly enjoyed ourselves and were happy with the villa. The location was awesome. We traveled throughout Tuscany and found the villa to be centrally locat..." - Maurice
Save $1,103 Photo of Charming Tuscany Farmhouse Walking Distance to town
  • min $8,051/wk
  • max $11,027/wk
  • min $7,246/wk
  • max $9,924/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,103 when you book by Jul-10-2020**
Save $309 Photo of Family-Friendly Apartment Close to Siena
  • min $1,616/wk
  • max $3,088/wk
  • min $1,454/wk
  • max $2,779/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $309 when you book by Jul-10-2020**
" The size of the bedrooms, bathrooms and the outside patio area...." - Monica
Save $216 Photo of Family-Friendly Apartment Close to Siena
  • min $1,133/wk
  • max $2,162/wk
  • min $1,020/wk
  • max $1,946/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $216 when you book by Jul-10-2020**
" Overall the property and atmosphere were great. The location was convenient to Siena and we found this to be very enjoyable, much more so than Florence...." - Peter
Save $934 Photo of Sophisticated Villa in a Village in Southern Tuscany
  • min $5,601/wk
  • max $9,335/wk
  • min $5,041/wk
  • max $8,402/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 2 single bedrooms
  • 3 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $934 when you book by Jul-10-2020**
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Jul-10-2020**
Save $1,444 Photo of Elegant Tuscan Country Villa with Rich Landscape
  • min $10,098/wk
  • max $14,439/wk
  • min $9,088/wk
  • max $12,995/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $1,444 when you book by Jul-10-2020**
Save $2,743 Photo of Historic Tuscan Villa with Cottage with Private Pool and Tennis Court
  • min $18,357/wk
  • max $27,430/wk
  • min $16,521/wk
  • max $24,687/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,743 when you book by Jul-10-2020**
Save $1,033 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $7,350/wk
  • max $10,325/wk
  • min $6,615/wk
  • max $9,293/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,033 when you book by Jul-10-2020**
Save $1,985 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $13,608/wk
  • max $19,845/wk
  • min $12,247/wk
  • max $17,861/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 $1,985 when you book by Jul-10-2020**
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 Jul-10-2020**
Save $3,481 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
  • min $27,668/wk
  • max $34,808/wk
  • min $24,901/wk
  • max $31,327/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $3,481 when you book by Jul-10-2020**
Save $508 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,078/wk
  • max $5,082/wk
  • min $970/wk
  • max $4,574/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $508 when you book by Jul-10-2020**
Save $508 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,078/wk
  • max $5,082/wk
  • min $970/wk
  • max $4,574/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $508 when you book by Jul-10-2020**
Save $508 Photo of Farmhouse Rental in Tuscany, Sarteano
  • min $1,078/wk
  • max $5,082/wk
  • min $970/wk
  • max $4,574/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $508 when you book by Jul-10-2020**
Save $2,086 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • min $14,000/wk
  • max $20,860/wk
  • min $12,600/wk
  • max $18,774/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,086 when you book by Jul-10-2020**
Save $415 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $3,157/wk
  • max $4,148/wk
  • min $2,841/wk
  • max $3,733/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $415 when you book by Jul-10-2020**
Save $910 Photo of Villa Rental in Tuscany, Monticchiello
  • min $4,061/wk
  • max $9,102/wk
  • min $3,655/wk
  • max $8,192/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $910 when you book by Jul-10-2020**
Save $2,835 Photo of Estate Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $21,528/wk
  • max $28,354/wk
  • min $19,375/wk
  • max $25,519/wk
  • Min Stay: 7 days
Sleeps 28 people
  • 14 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $2,835 when you book by Jul-10-2020**
Save $490 Photo of House Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $3,501/wk
  • max $4,901/wk
  • min $3,151/wk
  • max $4,411/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Swimming Pool
** Save up to $490 when you book by Jul-10-2020**
Save $2,100 Photo of Villa Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $16,803/wk
  • max $21,003/wk
  • min $15,123/wk
  • max $18,903/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $2,100 when you book by Jul-10-2020**
Save $1,246 Photo of Villa Rental in Tuscany, Pienza
  • min $5,461/wk
  • max $12,462/wk
  • min $4,915/wk
  • max $11,216/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,246 when you book by Jul-10-2020**
 
Displaying 61 to 90 of 92 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..