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Under the Tuscan Sun Villas and Vacation Rentals

You've dreamt of the rolling Tuscan hills; glasses of ruby-red Classico; villas framed with the orange glow of the setting sun; medieval hill towns outlined on the horizon... So come experience Italian life at its best, under the Tuscan sun. 

Displaying 31 to 60 of 52 villas
Save $1,470 Photo of Rural Woodland Tuscan villa with Pool and BBQ near Montaione
  • min $8,402/wk
  • max $14,702/wk
  • min $7,562/wk
  • max $13,232/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,470 when you book by Aug-10-2020**
Save $2,373 Photo of Large Resort Estate in Umbria Ideal for Large Groups
  • min $15,822/wk
  • max $23,733/wk
  • min $14,240/wk
  • max $21,360/wk
  • Min Stay: 7 days
Sleeps 26 people
  • 13 double bedrooms
  • 13 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,373 when you book by Aug-10-2020**
Save $496 Photo of Tuscany Villa with Four Bedrooms all with En Suite Baths
  • min $3,000/wk
  • max $4,961/wk
  • min $2,700/wk
  • max $4,465/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $496 when you book by Aug-10-2020**
" Truly excellent. The only thing that could have been better would have been the weather...." - James
Save $2,450 Photo of Luxury Villa Rental Near Siena
  • min $21,703/wk
  • max $24,503/wk
  • min $19,533/wk
  • max $22,053/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,450 when you book by Aug-10-2020**
" The villa was lovely...." - Phyllis
Save $2,764 Photo of Beautiful Italian Villa near Volterra for Large Group
  • min $7,743/wk
  • max $11,762/wk
  • min $5,923/wk
  • max $10,586/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,764 when you book by Aug-10-2020**
" Excellent. It exceeded my expectations. ..." - Louis
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 Aug-10-2020**
" 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 $210 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,401/wk
  • max $2,101/wk
  • min $1,261/wk
  • max $1,891/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Aug-10-2020**
" Great. Claudia and Rudi terrific ..." - Frank
Save $375 Photo of Villa with Pool Near Cortona in the Valdichiana
  • min $2,941/wk
  • max $3,754/wk
  • min $2,647/wk
  • max $3,379/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $375 when you book by Aug-10-2020**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
Save $378 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • min $3,500/wk
  • max $3,780/wk
  • min $3,150/wk
  • max $3,402/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $378 when you book by Aug-10-2020**
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
Save $392 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $938/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $392 when you book by Aug-10-2020**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
Save $600 Photo of Tuscany Villa Near Florence
  • min $3,500/wk
  • max $6,000/wk
  • min $3,150/wk
  • max $5,400/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $600 when you book by Aug-10-2020**
" The property is gorgeous and nicely furnished...." - Deann
Save $3,851 Photo of Private luxury villa near Florence with pool, tennis court, beautiful gardens, spectacular views.
  • min $17,503/wk
  • max $38,505/wk
  • min $15,753/wk
  • max $34,655/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,851 when you book by Aug-10-2020**
Save $1,260 Photo of Beautiful Chianti Villa with Guest Cottage and Private Infinity Pool
  • min $9,522/wk
  • max $12,602/wk
  • min $8,570/wk
  • max $11,342/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,260 when you book by Aug-10-2020**
" It was fantastic. ..." - Jessica
Save $1,497 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,374/wk
  • max $5,734/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,497 when you book by Aug-10-2020**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $722 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,794/wk
  • max $3,073/wk
  • min $1,372/wk
  • max $2,766/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $722 when you book by Aug-10-2020**
" Fantastic, better than our high expectations!..." - Harri
Save $1,033 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $7,350/wk
  • max $10,325/wk
  • min $6,615/wk
  • max $9,293/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,033 when you book by Aug-10-2020**
Save $2,984 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $8,439/wk
  • max $12,696/wk
  • min $6,456/wk
  • max $11,426/wk
  • Min Stay: 7 days
Sleeps 13 to 20 people
  • 7 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,984 when you book by Aug-10-2020**
" Wonderful! We had a group of 15, and everyone agrees that this villa and hostess are superior. We were there two weeks, and each day was better than the one before..." - Pamela
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 Aug-10-2020**
Save $1,755 Photo of Luxury Chianti Villa Near a Small Town
  • min $11,424/wk
  • max $17,553/wk
  • min $10,282/wk
  • max $15,798/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,755 when you book by Aug-10-2020**
" What a lovely villa! The location was perfect to get away from the crowds of Florence. Such a beautiful setting amongst the olive trees and vineyards nearby...." - Cyndi
Save $1,985 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $13,608/wk
  • max $19,845/wk
  • min $12,247/wk
  • max $17,861/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 $1,985 when you book by Aug-10-2020**
Save $1,050 Photo of Gorgeous Toscana Villa with pools, private garden and views
  • min $6,126/wk
  • max $10,502/wk
  • min $5,513/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Aug-10-2020**
Save $2,940 Photo of Estate Rental in Tuscany, Montaione
  • min $16,800/wk
  • max $29,400/wk
  • min $15,120/wk
  • max $26,460/wk
  • Min Stay: 3 days
Sleeps 32 people
  • 6 single bedrooms
  • 13 double bedrooms
  • 19 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $2,940 when you book by Aug-10-2020**
 
Displaying 31 to 60 of 52 villas