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Accommodations Tuscany Villa & Home 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 1 to 30 of 33 villas
Save $1,382 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,041/wk
  • max $10,082/wk
  • min $4,499/wk
  • max $9,074/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,382 when you book by Nov-30-2020**
" There were 13 of us, 8 adults and 5 children ages 6 to 10. All had a great time and there was plenty of room for all. The adults particularly enjoyed sitting on th..." - Michael
Save $404 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,039/wk
  • min $2,159/wk
  • max $3,635/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $404 when you book by Nov-30-2020**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $734 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,419/wk
  • max $7,341/wk
  • min $5,777/wk
  • max $6,607/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $734 when you book by Nov-30-2020**
  • min $5,515/wk
  • max $8,959/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" We loved this experience! We were there for 2 weeks in August and had different groups of people coming to stay with us. The property is part of a working farm (..." - Marty
Save $490 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,276/wk
  • max $4,901/wk
  • min $2,048/wk
  • max $4,411/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $490 when you book by Nov-30-2020**
" The view was great. ..." - Charlotte
Save $401 Photo of House Rental in Tuscany, Buonconvento
  • min $1,881/wk
  • max $4,013/wk
  • min $1,693/wk
  • max $3,612/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $401 when you book by Nov-30-2020**
Save $1,765 Photo of Villa Rental in Tuscany, Buonconvento
  • min $10,086/wk
  • max $17,651/wk
  • min $9,077/wk
  • max $15,886/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,765 when you book by Nov-30-2020**
Save $210 Photo of Tuscany Villa Rental
  • min $1,470/wk
  • max $2,100/wk
  • min $1,323/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $210 when you book by Nov-30-2020**
" Enjoyed location due to plenty of hiking opportunities with our dog. The property is fine for two people or perhaps a small family. Wouldn't recommend it for t..." - Peter
Save $1,151 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $5,228/wk
  • max $11,506/wk
  • min $4,705/wk
  • max $10,355/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,151 when you book by Nov-30-2020**
Save $1,405 Photo of Villa Rental in Tuscany, Lucignano d'Asso
  • min $12,433/wk
  • max $14,053/wk
  • min $11,190/wk
  • max $12,648/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,405 when you book by Nov-30-2020**
Save $1,390 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,435/wk
  • max $13,895/wk
  • min $7,592/wk
  • max $12,506/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,390 when you book by Nov-30-2020**
" Relaxing We loved it. The stunning views really made us know we were in Tuscany...probably the most beautiful part of Tuscany. Although narrow winding dirt roads ..." - Val
Save $931 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $5,881/wk
  • max $9,312/wk
  • min $5,293/wk
  • max $8,381/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $931 when you book by Nov-30-2020**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
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 Nov-30-2020**
" Very nice!..." - Tom
Save $490 Photo of Villa near Montalcino
  • min $3,675/wk
  • max $4,900/wk
  • min $3,308/wk
  • max $4,410/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $490 when you book by Nov-30-2020**
" It was like our own villa. The owners were so helpful in making everything work and we enjoyed our holiday. The sun room was a special place. We set it up as o..." - Geoff
Save $1,288 Photo of Villa Rental in Tuscany, Pienza
  • min $5,461/wk
  • max $12,882/wk
  • min $4,915/wk
  • max $11,594/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 $1,288 when you book by Nov-30-2020**
Save $4,852 Photo of Villa Rental in Tuscany, Montepulciano
  • min $30,874/wk
  • max $48,516/wk
  • min $27,787/wk
  • max $43,664/wk
  • Min Stay: 4 days
Sleeps 24 people
  • 12 double bedrooms
  • 12 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $4,852 when you book by Nov-30-2020**
Save $942 Photo of Villa Rental in Tuscany, Monticchiello
  • min $4,061/wk
  • max $9,419/wk
  • min $3,655/wk
  • max $8,477/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $942 when you book by Nov-30-2020**
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 Nov-30-2020**
Save $522 Photo of Farmhouse Rental in Tuscany, Sarteano
  • min $1,078/wk
  • max $5,221/wk
  • min $970/wk
  • max $4,699/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $522 when you book by Nov-30-2020**
Save $805 Photo of Charming Tuscany Farmhouse Walking Distance to town
  • $8,051/wk
  • $7,246/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 $805 when you book by Nov-30-2020**
Save $2,169 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $13,608/wk
  • max $21,688/wk
  • min $12,247/wk
  • max $19,519/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 $2,169 when you book by Nov-30-2020**
Save $1,909 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,163/wk
  • max $19,093/wk
  • min $10,947/wk
  • max $17,184/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,909 when you book by Nov-30-2020**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
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 Nov-30-2020**
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 Nov-30-2020**
Save $1,520 Photo of Villa Rental in Tuscany, San Casciano dei Bagni
  • min $14,000/wk
  • max $15,197/wk
  • min $12,600/wk
  • max $13,677/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,520 when you book by Nov-30-2020**
Save $522 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,078/wk
  • max $5,221/wk
  • min $970/wk
  • max $4,699/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $522 when you book by Nov-30-2020**
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 Nov-30-2020**
Save $890 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
  • $8,900/wk
  • $8,010/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $890 when you book by Nov-30-2020**
Save $3,481 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
  • min $22,400/wk
  • max $34,808/wk
  • min $20,160/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 Nov-30-2020**
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 Nov-30-2020**
 
Displaying 1 to 30 of 33 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..