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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 53 villas
Save $676 Photo of Elegant countryside Tuscan villa with pool near historic town, restaurants, attractions.
  • $6,763/wk
  • $6,087/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $676 when you book by Feb-29-2020**
" Absolutely fabulous! The views from every window and the expansive outdoor areas are breathtaking. The owner/host, Palmi, was accommodating, generous, thoughtful ..." - Eric
Save $1,115 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,319/wk
  • max $11,152/wk
  • min $6,587/wk
  • max $10,037/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,115 when you book by Feb-29-2020**
" The property is in a fabulous location with incredible 360 views- including a view to Florence. The house is over 500 years old but has been modernized with 7 bed..." - Robert
Save $1,271 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,215/wk
  • max $12,712/wk
  • min $7,393/wk
  • max $11,441/wk
  • Min Stay: 4 days
Sleeps 19 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,271 when you book by Feb-29-2020**
" This was one of the best large group trips we have ever taken. The place was far better than we expected. Paolo, the owner/architect was a charming guy who was t..." - Richard
Save $4,509 Photo of Large Resort Estate in Umbria Ideal for Large Groups
  • min $15,822/wk
  • max $23,733/wk
  • min $12,816/wk
  • max $19,224/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 $4,509 when you book by Feb-29-2020**
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 Feb-29-2020**
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 Feb-29-2020**
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
Save $1,106 Photo of Beautiful Hilltop Villa in Tuscany with Spectacular Views
  • min $4,621/wk
  • max $11,062/wk
  • min $4,159/wk
  • max $9,956/wk
  • Min Stay: 7 days
Sleeps 13 to 18 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,106 when you book by Feb-29-2020**
" Our group cherishes relationships and therefore thoughtfulness, condsideration and a desire to serve are a valuable component of our friendships. Upon meeting Ale..." - Mark
Save $490 Photo of Villa Near Cortona with a Private Pool
  • min $3,080/wk
  • max $4,900/wk
  • min $2,772/wk
  • max $4,410/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $490 when you book by Feb-29-2020**
" We loved our villa! The home was a vision of what, in our minds, Tuscany would look like. It was so comfortable and perfect for our stay. Louisa was darling and ..." - Cindy
Save $1,176 Photo of Beautiful Italian Villa near Volterra for Large Group
  • min $7,743/wk
  • max $11,762/wk
  • min $6,969/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 $1,176 when you book by Feb-29-2020**
" Excellent. It exceeded my expectations. ..." - Louis
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 Feb-29-2020**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
Save $307 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,794/wk
  • max $3,073/wk
  • min $1,615/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 $307 when you book by Feb-29-2020**
" Fantastic, better than our high expectations!..." - Harri
Save $317 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $993/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 $317 when you book by Feb-28-2020**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
Save $1,210 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,573/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 $1,210 when you book by Feb-28-2020**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $2,199 Photo of Luxury Tuscany Villa Near Lucca and Walking Distance to a Small Village
  • $21,994/wk
  • $19,795/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,199 when you book by Feb-29-2020**
" The villa was spectacular, even better than the photos. The grounds and surrounding areas were beautiful. It has been recently renovated and the owner spared no ..." - Elyce
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 Feb-29-2020**
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 Feb-29-2020**
Save $1,575 Photo of Rural Lucca Villa with Pool and Spectacular Views
  • min $9,627/wk
  • max $15,752/wk
  • min $8,664/wk
  • max $14,177/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,575 when you book by Feb-29-2020**
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 Feb-29-2020**
" The property is gorgeous and nicely furnished...." - Deann
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 Feb-29-2020**
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 Feb-29-2020**
" 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 $1,276 Photo of Large Villa Rental near Vorno, Lucca with Air Conditioning
  • $12,759/wk
  • $11,483/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 $1,276 when you book by Feb-29-2020**
" Pool area, kitchen, comfortable furnishings...." - Colleen
Save $1,925 Photo of Villa Rental in Tuscany, Montespertoli (Chianti Area)
  • min $8,750/wk
  • max $19,250/wk
  • min $7,875/wk
  • max $17,325/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $1,925 when you book by Feb-29-2020**
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 Feb-29-2020**
 
Displaying 31 to 60 of 53 villas