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Tuscany Villas Under The Tuscan Sun

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 1 to 30 of 59 villas
Save $416 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,130/wk
  • min $1,774/wk
  • max $3,717/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $416 when you book by Dec-15-2018**
" Couldn't have been any better. Loved every minute...." - Kathy
Save $930 Photo of Villa on Large Estate Near San Gimignano
  • min $4,500/wk
  • max $9,300/wk
  • min $4,050/wk
  • max $8,370/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $930 when you book by Dec-20-2018**
" Wonderful stay at the property. ..." - Robin
Save $784 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $7,841/wk
  • min $5,041/wk
  • max $7,057/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $784 when you book by Dec-20-2018**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $356 Photo of Tuscany Villa Rental in Chianti
  • min $1,888/wk
  • max $3,558/wk
  • min $1,699/wk
  • max $3,202/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $356 when you book by Dec-20-2018**
" The experience was amazing. It was two perfect weeks...." - Michael
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 Dec-20-2018**
" Truly excellent. The only thing that could have been better would have been the weather...." - James
Save $511 Photo of Large Villa with Pool Near Arezzo
  • min $1,637/wk
  • max $5,110/wk
  • min $1,473/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 Dec-20-2018**
" Amazing. Loved every aspect of it. ..." - Candy
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 Dec-20-2018**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
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: 5 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 Dec-20-2018**
" Loved La Solaia, very cozy and comfortable and it was everything we hoped for and more. The location was excellent to surrounding areas and the views were to die f..." - John
Save $396 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,084/wk
  • max $3,963/wk
  • min $1,876/wk
  • max $3,567/wk
  • Min Stay: 5 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 Dec-20-2018**
" Terrific. ..." - Claudia
Save $728 Photo of Tuscany Villa Rental
  • min $3,361/wk
  • max $7,281/wk
  • min $3,025/wk
  • max $6,553/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $728 when you book by Dec-20-2018**
" It was good...." - William
Save $669 Photo of Charming Villa in Tuscan Countryside near Forcoli
  • min $3,890/wk
  • max $6,690/wk
  • min $3,501/wk
  • max $6,021/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $669 when you book by Dec-20-2018**
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Dec-20-2018**
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
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 Dec-20-2018**
Save $1,330 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,074/wk
  • max $13,300/wk
  • min $7,267/wk
  • max $11,970/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,330 when you book by Dec-20-2018**
" 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 $252 Photo of Restored Farmhouse Surrounded by Vineyards and Olive Groves, Centrally Located in Tuscany
  • min $1,762/wk
  • max $2,521/wk
  • min $1,586/wk
  • max $2,269/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $252 when you book by Dec-20-2018**
" Great. Claudia and Rudi terrific ..." - Frank
Save $1,733 Photo of Luxury Chianti Villa Near a Small Town
  • min $11,375/wk
  • max $17,325/wk
  • min $10,238/wk
  • max $15,593/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,733 when you book by Dec-20-2018**
" 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 $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 Dec-20-2018**
" The villa was lovely...." - Phyllis
Save $1,105 Photo of Beautiful Italian Villa near Volterra for Large Group
  • min $6,217/wk
  • max $11,048/wk
  • min $5,595/wk
  • max $9,943/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,105 when you book by Dec-20-2018**
" A delightful stay at a lovely villa with incredible views...." - Kay
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 Dec-20-2018**
Save $308 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,519/wk
  • max $3,079/wk
  • min $1,367/wk
  • max $2,771/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $308 when you book by Dec-20-2018**
" In very good condition. A real retreat with a fantastic view..." - Andrew
Save $812 Photo of Farmhouse on Historic Estate in the Chianti
  • min $4,464/wk
  • max $8,123/wk
  • min $4,018/wk
  • max $7,311/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $812 when you book by Dec-20-2018**
" Our group of ten had a very enjoyable experience at the property...." - Marv
Save $181 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,520/wk
  • max $1,814/wk
  • min $1,368/wk
  • max $1,633/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $181 when you book by Dec-20-2018**
" Beautiful property, apartment well-appointed. Claudia and Rudi very friendly and helpful finding local eateries, grocery stores. Very quiet and although we were ..." - Susan
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 Dec-20-2018**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $569 Photo of Villa in Tuscany in a Small Village
  • min $4,622/wk
  • max $5,689/wk
  • min $4,160/wk
  • max $5,120/wk
  • Min Stay: 7 days
Sleeps 9 to 10 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $569 when you book by Dec-20-2018**
" We had a great time on our holiday. The villa is unique, which presents some challenges, but offers an authentic experience...." - Rob
Save $1,181 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $6,843/wk
  • max $11,808/wk
  • min $6,159/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 Dec-20-2018**
" 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 $1,575 Photo of Private Villa on a Castle Estate near Certaldo
  • min $11,639/wk
  • max $15,752/wk
  • min $10,475/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 Dec-20-2018**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $490 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,186/wk
  • max $4,901/wk
  • min $2,867/wk
  • max $4,411/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 $490 when you book by Dec-20-2018**
" We had a wonderful time at the property..." - Leo
Save $560 Photo of Charming Villa with Pool in Tuscany
  • min $3,641/wk
  • max $5,601/wk
  • min $3,277/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $560 when you book by Dec-20-2018**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 Dec-20-2018**
Save $1,091 Photo of Historic 16th Century Villa in Tuscany with  Private Pool and Shared Tennis Court
  • min $6,767/wk
  • max $10,905/wk
  • min $6,090/wk
  • max $9,815/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,091 when you book by Dec-20-2018**
" Of all the lovely places I've been, it's the one I most want to return to. Sooo relaxing--because of the peaceful, beautiful surroundings, the beauty of th..." - Anne
 
Displaying 1 to 30 of 59 villas