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 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 Nov-30-2022**
    " This was our second visit to this beautiful property. This time we stayed 2 weeks. The villa is beautiful and our family of twelve would definitely stay there ga..." - Stephen
    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 Nov-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 $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 Nov-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 Nov-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 Nov-30-2022**
    Save $572 Photo of Stunning  Montepulciano  villa    close  to  city  center,  with  views,  pool,  within  walking  distance  to  restaurants,  wine-tasting  and  shops!
    • $5,717/wk
    • $5,145/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $572 when you book by Nov-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 $721 Photo of Villa Rental in Tuscany, Montalcino
    • min $5,761/wk
    • max $7,205/wk
    • min $5,185/wk
    • max $6,485/wk
    • Min Stay: 7 days
    Sleeps 11 to 12 people
    • 6 double bedrooms
    • 6 bathrooms
    • Independent House
    • Swimming Pool
    ** Save up to $721 when you book by Nov-30-2022**
    Save $1,654 Photo of Villa Rental in Tuscany, Radicofani
    • $16,538/wk
    • $14,884/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 $1,654 when you book by Nov-30-2022**
    • Enquire for Rates
    Sleeps 18 people
    • 9 double bedrooms
    • 9 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Maid Service
    Save $3,087 Photo of Villa Rental in Tuscany, Montepulciano
    • $30,874/wk
    • $27,787/wk
    • Min Stay: 4 days
    Sleeps 16 people
    • 12 double bedrooms
    • 12 bathrooms
    • Independent House
    • Swimming Pool
    • Air Conditioning
    ** Save up to $3,087 when you book by Nov-30-2022**
    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 Nov-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 Nov-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 Nov-30-2022**
    Save $890 Photo of Villa Rental in Tuscany, Monteroni D'Arbia
    • $8,900/wk
    • $8,010/wk
    • Min Stay: 7 days
    Sleeps 12 people
    • 7 double bedrooms
    • 6 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $890 when you book by Nov-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 Nov-30-2022**
    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 Nov-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 Nov-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 $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 Nov-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 Nov-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 Nov-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 $1,870 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
    • min $14,766/wk
    • max $18,703/wk
    • min $13,289/wk
    • max $16,833/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 $1,870 when you book by Nov-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 Nov-30-2022**
    " Very nice!..." - Tom
    Save $815 Photo of Sophisticated Villa in a Village in Southern Tuscany
    • min $4,350/wk
    • max $8,148/wk
    • min $3,915/wk
    • max $7,333/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 $815 when you book by Nov-30-2022**
    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 Nov-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 $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 Nov-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..