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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 27 of 27 villas
    Save $1,038 Photo of Cozy Tuscan Villa near Montepulciano
    • min $5,461/wk
    • max $10,082/wk
    • min $4,423/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 $1,038 when you book by Sep-30-2021**
    " Excellent LOCATION! ..." - Charles
    Save $928 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 $9,281/wk
    • min $4,964/wk
    • max $8,353/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $928 when you book by Sep-30-2021**
    " 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 $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 Sep-30-2021**
    Save $220 Photo of Tuscany Villa Rental
    • min $1,536/wk
    • max $2,196/wk
    • min $1,382/wk
    • max $1,976/wk
    • Min Stay: 7 days
    Sleeps 4 people
    • 2 double bedrooms
    • 1 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    ** Save up to $220 when you book by Sep-30-2021**
    " 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 $490 Photo of Farmhouse in Southern Tuscany with Pool
    • min $2,801/wk
    • max $4,901/wk
    • min $2,521/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 Sep-30-2021**
    " The view was great. ..." - Charlotte
    Save $2,007 Photo of Villa Rental in Tuscany, Buonconvento
    • min $12,719/wk
    • max $20,065/wk
    • min $11,447/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-30-2021**
    Save $402 Photo of House Rental in Tuscany, Buonconvento
    • min $1,876/wk
    • max $4,019/wk
    • min $1,688/wk
    • max $3,617/wk
    • Min Stay: 7 days
    Sleeps 4 to 6 people
    • 2 double bedrooms
    • 2 bathrooms
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $402 when you book by Sep-30-2021**
    Save $813 Photo of Villa Rental in Tuscany, Montalcino
    • min $6,978/wk
    • max $8,134/wk
    • min $6,280/wk
    • max $7,321/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 $813 when you book by Sep-30-2021**
    Save $1,112 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
    • min $4,575/wk
    • max $11,120/wk
    • min $4,118/wk
    • max $10,008/wk
    • Min Stay: 7 days
    Sleeps 8 people
    • 4 double bedrooms
    • 4 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,112 when you book by Sep-30-2021**
    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 Sep-30-2021**
    " Excellent. Tuscany is exceptionally beautiful in the winter, and with the sun shining almost every day, all in all it was a lovely week...." - Judith
    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 Sep-30-2021**
    " Very cozy property, although a tiny kitchen for a property of that size...." - Anne
    Save $910 Photo of Villa Rental in Tuscany, Monticchiello
    • min $4,061/wk
    • max $9,102/wk
    • min $3,655/wk
    • max $8,192/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $910 when you book by Sep-30-2021**
    Save $1,176 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
    • min $5,881/wk
    • max $11,762/wk
    • min $5,293/wk
    • max $10,586/wk
    • Min Stay: 4 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,176 when you book by Sep-30-2021**
    " 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 Sep-30-2021**
    " Very nice!..." - Tom
    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 Sep-30-2021**
    " Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
    Save $1,225 Photo of Charming Tuscany Farmhouse Walking Distance to town
    • min $9,802/wk
    • max $12,252/wk
    • min $8,822/wk
    • max $11,027/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 $1,225 when you book by Sep-30-2021**
    Save $1,094 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
    • min $9,000/wk
    • max $10,935/wk
    • min $8,100/wk
    • max $9,842/wk
    • Min Stay: 7 days
    Sleeps 12 people
    • 7 double bedrooms
    • 6 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,094 when you book by Sep-30-2021**
    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 16 people
    • 12 double bedrooms
    • 12 bathrooms
    • Independent House
    • Swimming Pool
    • Air Conditioning
    ** Save up to $4,852 when you book by Sep-30-2021**
    Save $934 Photo of Sophisticated Villa in a Village in Southern Tuscany
    • min $5,601/wk
    • max $9,335/wk
    • min $5,041/wk
    • max $8,402/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 $934 when you book by Sep-30-2021**
    Save $962 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
    • $9,615/wk
    • $8,654/wk
    • Min Stay: 7 days
    Sleeps 8 people
    • 4 double bedrooms
    • 4 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $962 when you book by Sep-30-2021**
    " 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 $1,444 Photo of Elegant Tuscan Country Villa with Rich Landscape
    • min $10,099/wk
    • max $14,439/wk
    • min $9,089/wk
    • max $12,995/wk
    • Min Stay: 7 days
    Sleeps 12 people
    • 6 double bedrooms
    • 5 bathrooms
    • Independent House
    • Swimming Pool
    • Maid Service
    • Air Conditioning
    ** Save up to $1,444 when you book by Sep-30-2021**
    Save $2,166 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
    • min $14,766/wk
    • max $21,657/wk
    • min $13,289/wk
    • max $19,491/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 $2,166 when you book by Sep-30-2021**
    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 Sep-30-2021**
    Save $3,198 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
    • min $22,400/wk
    • max $31,982/wk
    • min $20,160/wk
    • max $28,784/wk
    • Min Stay: 7 days
    Sleeps 16 people
    • 8 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Air Conditioning
    ** Save up to $3,198 when you book by Sep-30-2021**
    Save $1,815 Photo of Villa Rental in Tuscany, Radicofani
    • min $15,024/wk
    • max $18,149/wk
    • min $13,522/wk
    • max $16,334/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 $1,815 when you book by Sep-30-2021**
    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 Sep-30-2021**
    Save $1,316 Photo of Villa Rental in Tuscany, Pienza
    • min $5,881/wk
    • max $13,162/wk
    • min $5,293/wk
    • max $11,846/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 $1,316 when you book by Sep-30-2021**
     
    Displaying 1 to 27 of 27 villas

      Show all 82 Villas and Houses for Rent in Siena

      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..