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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 91 to 120 of 101 villas
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 Jun-20-2019**
Save $312 Photo of Charming Apartment on a Large Estate in Monticchiello
  • min $2,353/wk
  • max $3,117/wk
  • min $2,118/wk
  • max $2,805/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $312 when you book by Jun-20-2019**
Save $1,444 Photo of Elegant Tuscan Country Villa with Rich Landscape
  • min $10,098/wk
  • max $14,438/wk
  • min $9,088/wk
  • max $12,994/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 Jun-20-2019**
Save $902 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Jun-20-2019**
Save $5,684 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $16,240/wk
  • max $20,300/wk
  • min $13,923/wk
  • max $16,443/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 $5,684 when you book by Jun-20-2019**
Save $294 Photo of Historic Apartment for a Couple in the Center of Siena
  • min $1,862/wk
  • max $2,940/wk
  • min $1,676/wk
  • max $2,646/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $294 when you book by Jun-20-2019**
Save $535 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $5,353/wk
  • min $938/wk
  • max $4,818/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $535 when you book by Jun-20-2019**
Save $535 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $5,353/wk
  • min $938/wk
  • max $4,818/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $535 when you book by Jun-20-2019**
Save $3,276 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
  • min $26,040/wk
  • max $32,760/wk
  • min $23,436/wk
  • max $29,484/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $3,276 when you book by Jun-20-2019**
Save $1,492 Photo of Villa Rental in Tuscany, San Casciano dei Bagni
  • min $13,818/wk
  • max $14,924/wk
  • min $12,436/wk
  • max $13,432/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,492 when you book by Jun-20-2019**
Save $341 Photo of Apartment for a Family in the Center of Siena
  • min $2,352/wk
  • max $3,411/wk
  • min $2,117/wk
  • max $3,070/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $341 when you book by Jun-20-2019**
 
Displaying 91 to 120 of 101 villas

Show all 511 Villas and Houses for Rent in Tuscany

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..