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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 25 of 25 villas
    Save $1,068 Photo of Cozy Tuscan Villa near Montepulciano
    • min $5,881/wk
    • max $10,677/wk
    • min $5,293/wk
    • max $9,609/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 $1,068 when you book by Jun-30-2022**
    " Excellent LOCATION! ..." - Charles
    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 Jun-30-2022**
    " 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 $929 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
    • min $5,717/wk
    • max $9,287/wk
    • min $5,145/wk
    • max $8,358/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $929 when you book by Jun-30-2022**
    " It was a dream vacation. It was one of the few times in my life that the reality exceeded my expectations. ..." - Marjorie
    Save $910 Photo of Sophisticated Villa in a Village in Southern Tuscany
    • min $4,350/wk
    • max $9,102/wk
    • min $3,915/wk
    • max $8,192/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 $910 when you book by Jun-30-2022**
    Save $1,704 Photo of Elegant Tuscan Country Villa with Rich Landscape
    • min $10,099/wk
    • max $17,037/wk
    • min $9,089/wk
    • max $15,333/wk
    • Min Stay: 7 days
    Sleeps 12 people
    • 6 double bedrooms
    • 5 bathrooms
    • Independent House
    • Swimming Pool
    • Maid Service
    • Air Conditioning
    ** Save up to $1,704 when you book by Jun-30-2022**
    Save $1,428 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
    • min $8,086/wk
    • max $14,282/wk
    • min $7,277/wk
    • max $12,854/wk
    • Min Stay: 4 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,428 when you book by Jun-30-2022**
    " Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
    Save $1,437 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
    • min $8,900/wk
    • max $14,374/wk
    • min $8,010/wk
    • max $12,937/wk
    • Min Stay: 7 days
    Sleeps 12 people
    • 7 double bedrooms
    • 6 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,437 when you book by Jun-30-2022**
    Save $1,009 Photo of Villa Rental in Tuscany, Montalcino
    • min $5,761/wk
    • max $10,092/wk
    • min $5,185/wk
    • max $9,083/wk
    • Min Stay: 7 days
    Sleeps 11 to 12 people
    • 6 double bedrooms
    • 6 bathrooms
    • Independent House
    • Swimming Pool
    ** Save up to $1,009 when you book by Jun-30-2022**
    Save $2,355 Photo of Villa Rental in Tuscany, Radicofani
    • min $16,538/wk
    • max $23,547/wk
    • min $14,884/wk
    • max $21,192/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 $2,355 when you book by Jun-30-2022**
    Save $864 Photo of Villa Rental in Tuscany, Montalcino
    • min $7,390/wk
    • max $8,636/wk
    • min $6,651/wk
    • max $7,772/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 $864 when you book by Jun-30-2022**
    Save $3,198 Photo of Converted farmhouse and cottages with pool in the heart of Tuscany wine country.
    • min $25,288/wk
    • max $31,982/wk
    • min $22,759/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 Jun-30-2022**
    Save $1,555 Photo of Villa Rental in Tuscany, Lucignano d'Asso
    • min $13,653/wk
    • max $15,550/wk
    • min $12,288/wk
    • max $13,995/wk
    • Min Stay: 7 days
    Sleeps 18 people
    • 9 double bedrooms
    • 9 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Maid Service
    ** Save up to $1,555 when you book by Jun-30-2022**
    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 Jun-30-2022**
    " Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
    Save $245 Photo of Tuscany Villa Rental
    • min $1,559/wk
    • max $2,449/wk
    • min $1,403/wk
    • max $2,204/wk
    • Min Stay: 7 days
    Sleeps 4 people
    • 2 double bedrooms
    • 1 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    ** Save up to $245 when you book by Jun-30-2022**
    " 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 $412 Photo of House Rental in Tuscany, Buonconvento
    • min $1,925/wk
    • max $4,117/wk
    • min $1,733/wk
    • max $3,705/wk
    • Min Stay: 7 days
    Sleeps 4 to 6 people
    • 2 double bedrooms
    • 2 bathrooms
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $412 when you book by Jun-30-2022**
    Save $1,165 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
    • min $6,230/wk
    • max $11,648/wk
    • min $5,607/wk
    • max $10,483/wk
    • Min Stay: 7 days
    Sleeps 8 people
    • 4 double bedrooms
    • 4 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,165 when you book by Jun-30-2022**
    Save $2,053 Photo of Villa Rental in Tuscany, Buonconvento
    • min $14,374/wk
    • max $20,526/wk
    • min $12,937/wk
    • max $18,473/wk
    • Min Stay: 7 days
    Sleeps 18 people
    • 9 double bedrooms
    • 9 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $2,053 when you book by Jun-30-2022**
    Save $1,008 Photo of Villa Rental in Tuscany, Monticchiello
    • min $4,061/wk
    • max $10,082/wk
    • min $3,655/wk
    • max $9,074/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,008 when you book by Jun-30-2022**
    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 Jun-30-2022**
    " Very nice!..." - Tom
    Save $2,120 Photo of Villa Rental in Tuscany, Sarteano
    • min $12,749/wk
    • max $21,198/wk
    • min $11,474/wk
    • max $19,078/wk
    • Min Stay: 7 days
    Sleeps 26 people
    • 13 double bedrooms
    • 13 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $2,120 when you book by Jun-30-2022**
    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 Jun-30-2022**
    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 Jun-30-2022**
    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 Jun-30-2022**
    Save $1,330 Photo of Villa Rental in Tuscany, Pienza
    • min $7,267/wk
    • max $13,302/wk
    • min $6,540/wk
    • max $11,972/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 $1,330 when you book by Jun-30-2022**
    Save $1,298 Photo of Villa Rental in Tuscany, Montalcino
    • min $6,844/wk
    • max $12,980/wk
    • min $6,160/wk
    • max $11,682/wk
    • Min Stay: 7 days
    Sleeps 10 people
    • 5 double bedrooms
    • 5 bathrooms
    • Swimming Pool
    • Air Conditioning
    ** Save up to $1,298 when you book by Jun-30-2022**
     
    Displaying 1 to 25 of 25 villas

      Show all 83 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..