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

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 Dec-20-2018**
" Fantastic experience with a beautiful area and facility...." - Kennth
Save $1,828 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $11,642/wk
  • max $18,275/wk
  • min $10,478/wk
  • max $16,448/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,828 when you book by Dec-20-2018**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
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 Dec-20-2018**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
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 Dec-20-2018**
" Very good...." - Bill
Save $420 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,501/wk
  • max $4,203/wk
  • min $2,251/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 Dec-20-2018**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
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 Dec-20-2018**
" Excellent overall experience. Property managers are the owners and are very nice and hospitable. ..." - Ralph
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 Dec-20-2018**
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" 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 $485 Photo of Villa Rental in Tuscany, Castlenuovo dell'Abate
  • min $4,667/wk
  • max $4,853/wk
  • min $4,200/wk
  • max $4,368/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $485 when you book by Dec-20-2018**
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 Dec-20-2018**
" 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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" 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 $1,213 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 Dec-20-2018**
Save $361 Photo of Farmhouse in Southern Tuscany with Pool
  • min $1,955/wk
  • max $3,609/wk
  • min $1,760/wk
  • max $3,248/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 $361 when you book by Dec-20-2018**
" The view was great. ..." - Charlotte
Save $932 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
  • min $5,740/wk
  • max $9,318/wk
  • min $5,166/wk
  • max $8,386/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $932 when you book by Dec-20-2018**
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 Dec-20-2018**
Save $1,470 Photo of Inviting Tuscan Farmhouse with Incredible Views and Privacy
  • min $9,800/wk
  • max $14,700/wk
  • min $8,820/wk
  • max $13,230/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 $1,470 when you book by Dec-20-2018**
Save $676 Photo of Villa Rental in Tuscany, Montalcino
  • min $5,782/wk
  • max $6,762/wk
  • min $5,204/wk
  • max $6,086/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 $676 when you book by Dec-20-2018**
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 Dec-20-2018**
" 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 $418 Photo of House Rental in Tuscany, Buonconvento
  • min $1,958/wk
  • max $4,176/wk
  • min $1,762/wk
  • max $3,758/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $418 when you book by Dec-20-2018**
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 Dec-20-2018**
" 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 $1,148 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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" Excellent. Villa was very clean and owners were very helpful...." - Gary
Save $762 Photo of Farmhouse with Private Pool and Beautiful Views in Southern Tuscany
  • $7,617/wk
  • $6,855/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $762 when you book by Dec-20-2018**
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
" Very nice!..." - Tom
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 Dec-20-2018**
" We had a fabulous time and would do it again in a heartbeat. ..." - Susan
Save $952 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $3,815/wk
  • max $9,520/wk
  • min $3,434/wk
  • max $8,568/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $952 when you book by Dec-20-2018**
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 Dec-20-2018**
" Amazing! Staying here was like being in paradise. ..." - Cassandra
 
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..