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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 57 villas
Save $1,181 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $7,869/wk
  • max $11,808/wk
  • min $7,082/wk
  • max $10,627/wk
  • Min Stay: 7 days
Sleeps 13 to 20 people
  • 7 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,181 when you book by Sep-20-2019**
" 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 $1,323 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,215/wk
  • max $13,228/wk
  • min $7,393/wk
  • max $11,905/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 $1,323 when you book by Sep-20-2019**
" 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 $324 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,699/wk
  • max $2,912/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $324 when you book by Sep-20-2019**
" Our experience was very soul-refreshing with the family at La Solaia. We enjoyed the location and the home. The kitchen was stocked with enough basic equipment to ..." - Dana
Save $396 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $2,064/wk
  • max $3,567/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $396 when you book by Sep-20-2019**
" Terrific. ..." - Claudia
Save $1,160 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,319/wk
  • max $11,603/wk
  • min $6,587/wk
  • max $10,443/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 $1,160 when you book by Sep-20-2019**
" Amazing. We has a wonderful time. ..." - Tim
Save $956 Photo of Chianti Villa near a Charming Village
  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Sep-20-2019**
" Great experience in a spectacular villa...." - Viviane
Save $490 Photo of Villa Near Cortona with a Private Pool
  • min $3,003/wk
  • max $4,900/wk
  • min $2,703/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 Sep-20-2019**
" 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 $511 Photo of Large Villa with Pool Near Arezzo
  • min $1,852/wk
  • max $5,110/wk
  • min $1,667/wk
  • max $4,599/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $511 when you book by Sep-20-2019**
" Wonderful. We loved the villa and the owner was very helpful The nights were cool and we kept the windows open...." - Becky
Save $1,050 Photo of Self Catering Accommodation in Tuscany
  • min $6,721/wk
  • max $10,502/wk
  • min $6,049/wk
  • max $9,452/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 $1,050 when you book by Sep-20-2019**
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
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 Sep-20-2019**
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 Sep-20-2019**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
Save $2,240 Photo of Luxury Villa Rental Near Siena
  • min $19,603/wk
  • max $22,403/wk
  • min $17,643/wk
  • max $20,163/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 $2,240 when you book by Sep-20-2019**
" The villa was lovely...." - Phyllis
Save $7,906 Photo of Villa Rental near Florence with Pool and Fruit Orchard
  • min $5,625/wk
  • max $16,875/wk
  • min $5,063/wk
  • max $15,188/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $7,906 when you book by Sep-20-2019**
" Fantastic. Beyond our expectations...." - Maggie
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 Sep-20-2019**
" It was wonderful. It is very comfortable and the views are magnificent. The landscaping is well done and interesting...." - Richard
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 Sep-20-2019**
" It was fantastic. ..." - Jessica
Save $637 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,970/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 $637 when you book by Sep-20-2019**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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 Sep-20-2019**
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 Sep-20-2019**
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 Sep-20-2019**
" The property is gorgeous and nicely furnished...." - Deann
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 Sep-20-2019**
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 Sep-20-2019**
" Pool area, kitchen, comfortable furnishings...." - Colleen
Save $941 Photo of Villa Rental Tuscany
  • min $4,900/wk
  • max $5,880/wk
  • min $4,410/wk
  • max $5,292/wk
  • Min Stay: 4 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $941 when you book by Sep-20-2019**
" Adequate space for a large group - wonderful views and ability to walk around. The manager at the reception was wonderful, efficient and accommodating...." - Sumaya
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 Sep-20-2019**
" 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 $2,109 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $14,459/wk
  • max $21,086/wk
  • min $13,013/wk
  • max $18,977/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 $2,109 when you book by Sep-20-2019**
Save $653 Photo of Villa for a Group Near Trasimeno Lake
  • min $4,107/wk
  • max $6,534/wk
  • min $3,696/wk
  • max $5,881/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $653 when you book by Sep-20-2019**
Save $1,755 Photo of Luxury Chianti Villa Near a Small Town
  • min $11,375/wk
  • max $17,553/wk
  • min $10,238/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 Sep-20-2019**
" 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 $5,304 Photo of Lucca Villa for Rent
  • min $39,782/wk
  • max $53,042/wk
  • min $35,804/wk
  • max $47,738/wk
  • Min Stay: 7 days
Sleeps 32 to 35 people
  • 17 double bedrooms
  • 16 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $5,304 when you book by Sep-20-2019**
 
Displaying 31 to 60 of 57 villas