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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 53 villas
Save $2,580 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,300/wk
  • min $4,770/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 $2,580 when you book by Nov-20-2019**
" Villa Dora exceeded our expectations in every way! We were a family of 6 adults and every one of us fell in love with the villa!..." - Lynn
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 Nov-20-2019**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $996 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,495/wk
  • max $3,202/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $996 when you book by Nov-20-2019**
" We loved our stay! The location is perfect and very peaceful. With a car everything is close and accessible. The villa was big for our family of 4 but we loved it...." - Pia
Save $1,389 Photo of Spacious and Beautiful Tuscany Villa Near Montalcino
  • min $8,432/wk
  • max $13,889/wk
  • min $7,589/wk
  • max $12,500/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,389 when you book by Nov-20-2019**
" 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 Nov-20-2019**
" Great. Claudia and Rudi terrific ..." - Frank
Save $943 Photo of Tuscany Villa with Four Bedrooms all with En Suite Baths
  • min $3,000/wk
  • max $4,961/wk
  • min $2,430/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 $943 when you book by Nov-20-2019**
" Truly excellent. The only thing that could have been better would have been the weather...." - James
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/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 $518 when you book by Nov-20-2019**
" Absolutely excellent. ..." - Kerby
Save $560 Photo of Tuscany Villa Rental near Greve
  • min $2,941/wk
  • max $5,601/wk
  • min $2,647/wk
  • max $5,041/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Nov-20-2019**
" Our stay was the highlight of our trip to Italy. ..." - Patty
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 Nov-20-2019**
" It was fantastic. ..." - Jessica
Save $906 Photo of Exclusive  Hilltop  Medieval  Villa  Features  Modern  Comforts,  Panoramic  Sea  Views,  Garden,  Pool  and  Jacuzzi  in  Pistoia,  Tuscany
  • min $2,661/wk
  • max $6,021/wk
  • min $2,258/wk
  • max $5,419/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $906 when you book by Nov-20-2019**
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/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 $588 when you book by Nov-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
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 Nov-20-2019**
" 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 $2,373 Photo of Large Resort Estate in Umbria Ideal for Large Groups
  • min $15,122/wk
  • max $23,733/wk
  • min $13,610/wk
  • max $21,360/wk
  • Min Stay: 3 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 Nov-20-2019**
Save $633 Photo of Umbrian Villa for 14 with Pool, Views, Social Area 
Perfect for Wedding and Reunions!
  • min $2,941/wk
  • max $5,661/wk
  • min $2,382/wk
  • max $5,095/wk
  • Min Stay: 4 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $633 when you book by Nov-20-2019**
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 Nov-20-2019**
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 Nov-20-2019**
" Absolutely fabulous! The views from every window and the expansive outdoor areas are breathtaking. The owner/host, Palmi, was accommodating, generous, thoughtful ..." - Eric
Save $1,138 Photo of Historic 16th Century Villa in Tuscany with  Private Pool and Shared Tennis Court
  • min $7,060/wk
  • max $11,377/wk
  • min $6,354/wk
  • max $10,239/wk
  • Min Stay: 4 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,138 when you book by Nov-20-2019**
" 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
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 Nov-20-2019**
" The villa was lovely...." - Phyllis
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 Nov-20-2019**
" Great experience in a spectacular villa...." - Viviane
Save $1,987 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $7,869/wk
  • max $12,696/wk
  • min $6,836/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 $1,987 when you book by Nov-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 $719 Photo of Lovely Villa with Countryside Views of Tuscany
  • min $3,493/wk
  • max $7,188/wk
  • min $3,144/wk
  • max $6,469/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $719 when you book by Nov-20-2019**
" Perfect!..." - Michal
Save $1,358 Photo of Private Villa on a Castle Estate near Certaldo
  • min $10,922/wk
  • max $13,582/wk
  • min $9,830/wk
  • max $12,224/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,358 when you book by Nov-20-2019**
" 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 $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 Nov-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 $906 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,359/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 $906 when you book by Nov-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 $1,110 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $1,651/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 $1,110 when you book by Nov-20-2019**
" Wonderful all around!..." - Cinnamon
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,337/wk
  • min $1,971/wk
  • max $3,903/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 $434 when you book by Nov-20-2019**
" It was magical. When you arrive and open the gate, you are surrounded by roses, hydrangeas, geraniums (with colors I'd never seen) and olive trees. The Villa..." - Joan
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 Nov-20-2019**
" We thoroughly enjoyed our stay. Alessandro couldn't have been nicer. He gave us directions to the local supermarkets and places of interest to visit...." - Robert
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 Nov-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 $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 Nov-20-2019**
" 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 $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 Nov-20-2019**
 
Displaying 1 to 30 of 53 villas