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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 43 villas
Save $924 Photo of Cozy Tuscan Villa near Montepulciano
  • min $4,761/wk
  • max $9,242/wk
  • min $4,285/wk
  • max $8,318/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 $924 when you book by Oct-31-2018**
" Fantastic experience with a beautiful area and facility...." - Kennth
Save $925 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,751/wk
  • max $4,623/wk
  • min $2,201/wk
  • max $3,699/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 $925 when you book by Oct-31-2018**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $4,021 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,806/wk
  • max $20,103/wk
  • min $10,245/wk
  • max $16,082/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,021 when you book by Oct-31-2018**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
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 Oct-31-2018**
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
Save $1,372 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $6,861/wk
  • max $13,722/wk
  • min $6,175/wk
  • max $12,350/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,372 when you book by Oct-31-2018**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $6,035 Photo of Historic Tuscan Villa with Cottage with Private Pool and Tennis Court
  • min $20,193/wk
  • max $30,173/wk
  • min $16,154/wk
  • max $24,138/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 $6,035 when you book by Oct-31-2018**
Save $2,909 Photo of Villa in Southern Tuscany with Privacy and Views
  • min $9,240/wk
  • max $14,543/wk
  • min $7,392/wk
  • max $11,634/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 $2,909 when you book by Oct-31-2018**
" Very good...." - Bill
Save $445 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,780/wk
  • max $2,224/wk
  • min $1,424/wk
  • max $1,779/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $445 when you book by Oct-31-2018**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
Save $794 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,151/wk
  • max $3,970/wk
  • min $1,720/wk
  • max $3,176/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 $794 when you book by Oct-31-2018**
" The view was great. ..." - Charlotte
Save $300 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $2,157/wk
  • max $3,002/wk
  • min $1,941/wk
  • max $2,702/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $300 when you book by Oct-31-2018**
" We had a very relaxing and enjoyable time at Casa dei Venti - La Tempesta. Our host, Filippo, was very kind and generous and helped us with several outings in the ..." - Jim
Save $1,488 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,360/wk
  • max $7,438/wk
  • min $5,088/wk
  • max $5,951/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,488 when you book by Oct-31-2018**
Save $534 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $2,076/wk
  • max $2,669/wk
  • min $1,661/wk
  • max $2,135/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $534 when you book by Oct-31-2018**
" We had a grand time. The staff were kind and exceedingly helpful. The town was a bit quiet, but we were close to some beautiful towns. ..." - Jamie
Save $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Oct-31-2018**
" Nice small property with charming hosts in a pretty area...." - Sara
Save $202 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,618/wk
  • max $2,022/wk
  • min $1,456/wk
  • max $1,820/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $202 when you book by Oct-31-2018**
" Excellent. In this unit were my wife's mom and our 11 year old twins. They spent more time in the facility while we went out sightseeing more. They loved the a..." - Curtis
Save $2,669 Photo of Charming Tuscany Farmhouse Walking Distance to town
  • min $11,860/wk
  • max $13,343/wk
  • min $9,488/wk
  • max $10,674/wk
  • Min Stay: 7 days
Sleeps 12 to 20 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,669 when you book by Oct-31-2018**
Save $3,234 Photo of Inviting Tuscan Farmhouse with Incredible Views and Privacy
  • min $10,780/wk
  • max $16,170/wk
  • min $8,624/wk
  • max $12,936/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $3,234 when you book by Oct-31-2018**
Save $1,260 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
  • min $8,528/wk
  • max $12,598/wk
  • min $7,675/wk
  • max $11,338/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Oct-31-2018**
Save $589 Photo of Tuscany Villa with Private Pool
  • min $3,199/wk
  • max $5,887/wk
  • min $2,879/wk
  • max $5,298/wk
  • Min Stay: 7 days
Sleeps 16 to 17 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
** Save up to $589 when you book by Oct-31-2018**
" We had a great experience. The owner, Antonella, was exceptionally helpful in so many ways. The property is lovely, and a great deal of thought has been given to..." - Felice
Save $462 Photo of Tuscany Villa Rental
  • min $1,617/wk
  • max $2,310/wk
  • min $1,294/wk
  • max $1,848/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $462 when you book by Oct-31-2018**
" 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 $1,068 Photo of Villa Rental in Tuscany, Castlenuovo dell'Abate
  • min $5,134/wk
  • max $5,338/wk
  • min $4,107/wk
  • max $4,271/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,068 when you book by Oct-31-2018**
Save $919 Photo of House Rental in Tuscany, Buonconvento
  • min $2,154/wk
  • max $4,594/wk
  • min $1,723/wk
  • max $3,675/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $919 when you book by Oct-31-2018**
Save $1,676 Photo of Farmhouse with Private Pool and Beautiful Views in Southern Tuscany
  • min $6,331/wk
  • max $8,379/wk
  • min $5,064/wk
  • max $6,703/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $1,676 when you book by Oct-31-2018**
Save $1,330 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,074/wk
  • max $13,300/wk
  • min $7,267/wk
  • max $11,970/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,330 when you book by Oct-31-2018**
" 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 $1,148 Photo of Large Villa in Tuscany with Two Pools
  • min $9,100/wk
  • max $11,480/wk
  • min $8,190/wk
  • max $10,332/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,148 when you book by Oct-31-2018**
" Our expectations were exceeded. We rented the villa for the month of October 2015. The property manager, is a master of customer service and charm...." - Alice
Save $1,201 Photo of Enchanting Tuscan Villa Near Montepulciano
  • min $3,697/wk
  • max $6,007/wk
  • min $2,958/wk
  • max $4,806/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,201 when you book by Oct-31-2018**
" There were three couples/friends sharing the villa. The three bedrooms downstairs were quite nice and all had their space. The owner was lovely. Accommodations for..." - Lee
Save $2,050 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $6,314/wk
  • max $10,250/wk
  • min $5,051/wk
  • max $8,200/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,050 when you book by Oct-31-2018**
Save $467 Photo of Villa near Montalcino
  • min $3,360/wk
  • max $4,667/wk
  • min $3,024/wk
  • max $4,200/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $467 when you book by Oct-31-2018**
" 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 $1,540 Photo of Tuscan Farmhouse with a Private Pool Near Spas
  • min $3,850/wk
  • max $7,700/wk
  • min $3,080/wk
  • max $6,160/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,540 when you book by Oct-31-2018**
" Very nice!..." - Tom
Save $1,706 Photo of Villa Rental in Tuscany, Buonconvento
  • min $9,826/wk
  • max $17,056/wk
  • min $8,843/wk
  • max $15,350/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,706 when you book by Oct-31-2018**
Save $3,234 Photo of Farmhouse Rental in Tuscany, Pienza
  • min $10,780/wk
  • max $16,170/wk
  • min $8,624/wk
  • max $12,936/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 $3,234 when you book by Oct-31-2018**
 
Displaying 1 to 30 of 43 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..