Suitcase

Your Suitcase contains your favorite villas and details of your upcoming trip. Sign up to use this feature.
Rated Excellent By Trip Advisor

Quick Filter

Travelers
Arrival Date
Departure Date
Max Price per Week

South Siena Villas and Vacation Rentals

If such a thing is possible, this may be Tuscany's most picturesque zone. South of Siena, the walled town of Montalcino and the Etruscan center of Chiusi are not to be missed.   Continue >

Displaying 31 to 60 of 43 villas
Save $3,124 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $14,553/wk
  • max $19,285/wk
  • min $11,788/wk
  • max $17,357/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 $3,124 when you book by Sep-30-2018**
Save $1,470 Photo of Farmhouse Rental in Tuscany, Pienza
  • min $9,800/wk
  • max $14,700/wk
  • min $8,820/wk
  • max $13,230/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,470 when you book by Sep-30-2018**
  • min $4,000/wk
  • max $6,700/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 $250 Photo of Apartment within a Villa in Southern Tuscany
  • min $2,059/wk
  • max $2,500/wk
  • min $1,853/wk
  • max $2,250/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $250 when you book by Sep-30-2018**
Save $781 Photo of Farmhouse Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $7,810/wk
  • min $938/wk
  • max $7,029/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $781 when you book by Sep-30-2018**
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 Sep-30-2018**
Save $782 Photo of Charming Farmhouse on a Large Estate in Monticchiello
  • min $5,822/wk
  • max $7,822/wk
  • min $5,240/wk
  • max $7,040/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $782 when you book by Sep-30-2018**
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 Sep-30-2018**
Save $858 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • min $7,980/wk
  • max $8,575/wk
  • min $7,182/wk
  • max $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 Sep-30-2018**
" 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 $3,276 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
  • min $25,340/wk
  • max $32,760/wk
  • min $22,806/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 Sep-30-2018**
Save $781 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $7,810/wk
  • min $938/wk
  • max $7,029/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $781 when you book by Sep-30-2018**
Save $1,041 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $10,413/wk
  • min $938/wk
  • max $9,372/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,041 when you book by Sep-30-2018**
Save $1,091 Photo of Elegant Tuscan Country Villa with Rich Landscape
  • min $6,550/wk
  • max $10,905/wk
  • min $5,895/wk
  • max $9,815/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $1,091 when you book by Sep-30-2018**
 
Displaying 31 to 60 of 43 villas

Show all 108 Villas and Houses for Rent in Siena

A walled town of Roman origins, Montalcino produces one of the finest red wines in Italy: Brunello di Montalcino. Although you could sip Brunello from dawn till dusk in Montalcino, the Cistercian abbey of Sant'Antimo---located near the town---is well worth a side trip. The Romanesque abbey's yellow and white stone makes its interior literally glow. Add the otherworldly sound of Gregorian chants (French monks have inhabited the abbey---which dates back to 1118---since 1992), and merely standing inside the abbey becomes a sublime experience. Pienza, home of pecorino cheese, is another worthwhile stop on the road eastward. One of the most powerful cities in the 12-city Etruscan federation, Chiusi boasts some of Southern Tuscany's most significant archaeology. Conveniently, it is also one of the main stops on the Florence – Rome line and is an exit off the A-1 autostrada. Montepulciano, 13 miles northeast of Chiusi, produces a red wine, called Vino Nobile di Montepulciano, that is second only to Montalcino's Brunello. To the southeast of Montepulciano lies Chianciano Terme, a famous Tuscan spa where you can soak in the thermal baths or drink the waters, which through the ages have been purported to cure a variety of ailments. Discover our Villas for rent in South Siena..