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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 44 villas
Save $455 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,554/wk
  • min $2,070/wk
  • max $4,099/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 $455 when you book by Sep-30-2021**
" We had a wonderful time. The house was beautiful and everything we expected. ..." - Theresa
Save $1,139 Photo of Historic 16th Century Villa in Tuscany with  Private Pool and Shared Tennis Court
  • min $7,070/wk
  • max $11,393/wk
  • min $6,363/wk
  • max $10,254/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,139 when you book by Sep-30-2021**
" Our family enjoyed the villa so much they wished they had more time to just enjoy the villa and stay on the property. From check-in to check-out, everyone made us ..." - Mary
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-30-2021**
" Great experience in a spectacular villa...." - Viviane
Save $770 Photo of Elegant countryside Tuscan villa with pool near historic town, restaurants, attractions.
  • $7,701/wk
  • $6,931/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 $770 when you book by Sep-30-2021**
" Absolutely fabulous! The views from every window and the expansive outdoor areas are breathtaking. The owner/host, Palmi, was accommodating, generous, thoughtful ..." - Eric
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 Sep-30-2021**
" Our stay was the highlight of our trip to Italy. ..." - Patty
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-30-2021**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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 Sep-30-2021**
" Had a wonderful experience Place was great..." - Paula
Save $770 Photo of Tuscany Villa Rental
  • min $3,361/wk
  • max $7,701/wk
  • min $3,025/wk
  • max $6,931/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $770 when you book by Sep-30-2021**
" It was good...." - William
Save $822 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $8,215/wk
  • min $5,041/wk
  • max $7,393/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $822 when you book by Sep-30-2021**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $1,050 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $10,502/wk
  • min $8,192/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Sep-30-2021**
" 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 $461 Photo of Lovely Villa with Countryside Views of Tuscany
  • min $3,493/wk
  • max $4,612/wk
  • min $3,144/wk
  • max $4,151/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $461 when you book by Sep-30-2021**
" Perfect!..." - Michal
Save $350 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • min $2,380/wk
  • max $3,500/wk
  • min $2,142/wk
  • max $3,150/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 $350 when you book by Sep-30-2021**
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
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 Sep-30-2021**
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-30-2021**
Save $560 Photo of Large Villa with Pool Near Arezzo
  • min $2,221/wk
  • max $5,604/wk
  • min $1,999/wk
  • max $5,044/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $560 when you book by Sep-30-2021**
" 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 $1,176 Photo of Beautiful Hilltop Villa in Tuscany with Spectacular Views
  • min $4,621/wk
  • max $11,762/wk
  • min $4,159/wk
  • max $10,586/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 $1,176 when you book by Sep-30-2021**
" 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 $990 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,900/wk
  • min $4,770/wk
  • max $8,910/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $990 when you book by Sep-30-2021**
" We absolutely LOVED our stay at Villa Dora! Every room was stunning, and the villa beautifully appointed. Every detail was perfect. The views, and outdoor spaces w..." - Patti
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 Sep-30-2021**
" 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 Sep-30-2021**
" 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 $630 Photo of Villa Near Cortona with a Private Pool
  • min $3,150/wk
  • max $6,300/wk
  • min $2,835/wk
  • max $5,670/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 $630 when you book by Sep-30-2021**
" 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 $560 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $3,221/wk
  • max $5,601/wk
  • min $2,899/wk
  • max $5,041/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 $560 when you book by Sep-30-2021**
" We loved the location the restored mill was beautiful, the home decor (mostly antiques were interesting), the internet was highly variable and could have lived for..." - Thomas
Save $1,460 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $9,335/wk
  • max $14,600/wk
  • min $8,402/wk
  • max $13,140/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 $1,460 when you book by Sep-30-2021**
" Overall, we had a very nice experience. The property is beautiful, the villa and the rooms are beautiful and all in a very peaceful setting. The proximity to the b..." - Craig
Save $147 Photo of Vacation Rental Agritourism in Tuscany
  • min $1,233/wk
  • max $1,471/wk
  • min $1,110/wk
  • max $1,324/wk
  • Min Stay: 4 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $147 when you book by Sep-30-2021**
" A wonderful place to relax...." - Ruth
Save $1,294 Photo of Beautiful Italian Villa near Volterra for Large Group
  • min $7,743/wk
  • max $12,938/wk
  • min $6,969/wk
  • max $11,644/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,294 when you book by Sep-30-2021**
" Excellent. It exceeded my expectations. ..." - Louis
Save $700 Photo of Umbrian Villa for 14 with Pool, Views, Social Area 
Perfect for Wedding and Reunions!
  • min $3,579/wk
  • max $7,001/wk
  • min $3,221/wk
  • max $6,301/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $700 when you book by Sep-30-2021**
" The bedrooms were comfortable and furnished beautifully the pictures were accurate and the kitchen was workable. Pretty good location once we found it, would have ..." - Janet
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 Sep-30-2021**
" Excellent. Tuscany is exceptionally beautiful in the winter, and with the sun shining almost every day, all in all it was a lovely week...." - Judith
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 Sep-30-2021**
" Great. Claudia and Rudi terrific ..." - Frank
Save $630 Photo of Exclusive  Hilltop  Medieval  Villa  Features  Modern  Comforts,  Panoramic  Sea  Views,  Garden,  Pool  and  Jacuzzi  in  Pistoia,  Tuscany
  • min $2,941/wk
  • max $6,301/wk
  • min $2,647/wk
  • max $5,671/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 $630 when you book by Sep-30-2021**
Save $350 Photo of Tuscany Villa Near Florence
  • $3,500/wk
  • $3,150/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $350 when you book by Sep-30-2021**
" The property is gorgeous and nicely furnished...." - Deann
Save $1,008 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $10,082/wk
  • min $6,049/wk
  • max $9,074/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 $1,008 when you book by Sep-30-2021**
" 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
 
Displaying 1 to 30 of 44 villas