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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 99 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 Sep-20-2019**
Save $675 Photo of Charming Farmhouse on a Large Estate in Monticchiello
  • min $5,822/wk
  • max $6,752/wk
  • min $5,240/wk
  • max $6,077/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $675 when you book by Sep-20-2019**
Save $1,632 Photo of Large Villa with Pool and Guest House in Chianti
  • min $9,399/wk
  • max $16,315/wk
  • min $8,459/wk
  • max $14,684/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 $1,632 when you book by Sep-20-2019**
Save $2,109 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $14,459/wk
  • max $21,086/wk
  • min $13,013/wk
  • max $18,977/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 $2,109 when you book by Sep-20-2019**
Save $2,120 Photo of Villa Rental in Tuscany, Radicofani
  • min $15,024/wk
  • max $21,197/wk
  • min $13,522/wk
  • max $19,077/wk
  • Min Stay: 7 days
Sleeps 17 people
  • 1 single bedrooms
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,120 when you book by Sep-20-2019**
Save $1,172 Photo of Villa Rental in Tuscany, Lucignano d'Asso
  • min $9,010/wk
  • max $11,716/wk
  • min $8,109/wk
  • max $10,544/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,172 when you book by Sep-20-2019**
Save $2,882 Photo of Villa Rental in Tuscany, Sarteano
  • min $19,845/wk
  • max $28,823/wk
  • min $17,861/wk
  • max $25,941/wk
  • Min Stay: 7 days
Sleeps 26 people
  • 13 double bedrooms
  • 13 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,882 when you book by Sep-20-2019**
Save $2,120 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • $21,198/wk
  • $19,078/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,120 when you book by Sep-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 Sep-20-2019**
 
Displaying 91 to 120 of 99 villas

Show all 473 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..