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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 $1,925 Photo of Cozy Tuscan Villa near Montepulciano
  • min $5,041/wk
  • max $9,242/wk
  • min $4,537/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 $1,925 when you book by Sep-20-2019**
" Awesome ..." - Trent
Save $1,389 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,432/wk
  • max $13,889/wk
  • min $7,589/wk
  • max $12,500/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,389 when you book by Sep-20-2019**
" 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 $420 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,203/wk
  • min $2,159/wk
  • max $3,783/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 $420 when you book by Sep-20-2019**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $1,294 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $6,077/wk
  • max $12,938/wk
  • min $5,469/wk
  • max $11,644/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,294 when you book by Sep-20-2019**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $1,909 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,157/wk
  • max $19,094/wk
  • min $10,941/wk
  • max $17,185/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 Sep-20-2019**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
Save $902 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Sep-20-2019**
Save $896 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,515/wk
  • max $8,959/wk
  • min $4,964/wk
  • max $8,063/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $896 when you book by Sep-20-2019**
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 Sep-20-2019**
" 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 $401 Photo of House Rental in Tuscany, Buonconvento
  • min $1,882/wk
  • max $4,013/wk
  • min $1,694/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 Sep-20-2019**
Save $221 Photo of Apartment within a Villa in Southern Tuscany
  • min $2,059/wk
  • max $2,206/wk
  • min $1,853/wk
  • max $1,985/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 $221 when you book by Sep-20-2019**
" Amazing! Staying here was like being in paradise. ..." - Cassandra
Save $706 Photo of Villa Rental in Tuscany, Montalcino
  • min $6,174/wk
  • max $7,056/wk
  • min $5,557/wk
  • max $6,350/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 $706 when you book by Sep-20-2019**
Save $670 Photo of Sophisticated Villa in a Village in Southern Tuscany
  • min $4,000/wk
  • max $6,700/wk
  • min $3,600/wk
  • max $6,030/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 up to $670 when you book by Sep-20-2019**
Save $411 Photo of Farmhouse in Southern Tuscany with Pool
  • min $2,276/wk
  • max $4,114/wk
  • min $2,048/wk
  • max $3,703/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 $411 when you book by Sep-20-2019**
" The view was great. ..." - Charlotte
Save $980 Photo of Large Villa in Tuscany with Two Pools
  • $9,800/wk
  • $8,820/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $980 when you book by Sep-20-2019**
" 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 $2,007 Photo of Villa Rental in Tuscany, Buonconvento
  • min $15,088/wk
  • max $20,065/wk
  • min $13,579/wk
  • max $18,059/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,007 when you book by Sep-20-2019**
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 Sep-20-2019**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
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 Sep-20-2019**
" 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 $243 Photo of Charming Tuscany Apartment Walking Distance to town
  • min $1,887/wk
  • max $2,426/wk
  • min $1,698/wk
  • max $2,183/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 $243 when you book by Sep-20-2019**
" 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 Sep-20-2019**
" 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 Sep-20-2019**
" 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 $1,213 Photo of Charming Tuscany Farmhouse Walking Distance to town
  • min $10,782/wk
  • max $12,130/wk
  • min $9,704/wk
  • max $10,917/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 $1,213 when you book by Sep-20-2019**
Save $1,111 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $3,815/wk
  • max $11,114/wk
  • min $3,434/wk
  • max $10,003/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,111 when you book by Sep-20-2019**
Save $546 Photo of Enchanting Tuscan Villa Near Montepulciano
  • min $3,361/wk
  • max $5,461/wk
  • min $3,025/wk
  • max $4,915/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 $546 when you book by Sep-20-2019**
" Excellent. Villa was very clean and owners were very helpful...." - Gary
Save $271 Photo of Charming Apartment on a Large Estate in Monticchiello
  • min $2,353/wk
  • max $2,706/wk
  • min $2,118/wk
  • max $2,435/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $271 when you book by Sep-20-2019**
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
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 Sep-20-2019**
" 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 $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-20-2019**
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 Sep-20-2019**
" Very nice!..." - Tom
Save $1,050 Photo of Villa in Southern Tuscany with Privacy and Views
  • min $8,400/wk
  • max $10,500/wk
  • min $7,560/wk
  • max $9,450/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 $1,050 when you book by Sep-20-2019**
" Very good...." - Bill
Save $962 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • min $8,575/wk
  • max $9,615/wk
  • min $7,718/wk
  • max $8,654/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $962 when you book by Sep-20-2019**
" 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 $271 Photo of Charming Apartment on a Large Estate in Monticchiello
  • min $2,353/wk
  • max $2,706/wk
  • min $2,118/wk
  • max $2,435/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $271 when you book by Sep-20-2019**
 
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..