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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 37 villas
  • min $5,755/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • min $25,940/wk
  • max $33,961/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
  • min $2,059/wk
  • max $2,500/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • 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
  • min $2,353/wk
  • max $3,117/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $11,256/wk
  • max $13,221/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very good...." - Bill
 
Displaying 31 to 60 of 37 villas

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..