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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 51 villas
Save $1,881 Photo of Villa on Large Estate Near San Gimignano
  • min $5,300/wk
  • max $9,900/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 $1,881 when you book by Oct-31-2020**
" 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 Oct-31-2020**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $366 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,662/wk
  • min $1,869/wk
  • max $3,296/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $366 when you book by Oct-31-2020**
" 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 $511 Photo of Large Villa with Pool Near Arezzo
  • min $2,126/wk
  • max $5,110/wk
  • min $1,913/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 Oct-31-2020**
" 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 $345 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,448/wk
  • min $1,699/wk
  • max $3,103/wk
  • Min Stay: 4 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $345 when you book by Oct-31-2020**
" 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 $409 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $4,093/wk
  • min $2,064/wk
  • max $3,684/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 $409 when you book by Oct-31-2020**
" Wonderful all around!..." - Cinnamon
Save $3,450 Photo of Villa Rental near Florence with Pool and Fruit Orchard
  • min $7,500/wk
  • max $16,875/wk
  • min $4,050/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 $3,450 when you book by Oct-31-2020**
" Fantastic. Beyond our expectations...." - Maggie
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 Oct-31-2020**
" Excellent. It exceeded my expectations. ..." - Louis
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 Oct-31-2020**
" 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 $532 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,321/wk
  • min $2,206/wk
  • max $4,789/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 $532 when you book by Oct-31-2020**
" Absolutely excellent. ..." - Kerby
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 Oct-31-2020**
" Absolutely fabulous! The views from every window and the expansive outdoor areas are breathtaking. The owner/host, Palmi, was accommodating, generous, thoughtful ..." - Eric
Save $4,852 Photo of Villa Rental in Tuscany, Montepulciano
  • min $30,874/wk
  • max $48,516/wk
  • min $27,787/wk
  • max $43,664/wk
  • Min Stay: 4 days
Sleeps 24 people
  • 12 double bedrooms
  • 12 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $4,852 when you book by Oct-31-2020**
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 Oct-31-2020**
" 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 $2,373 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 Oct-31-2020**
Save $581 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,811/wk
  • min $2,521/wk
  • max $5,230/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 $581 when you book by Oct-31-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $760 Photo of Umbrian Villa for 14 with Pool, Views, Social Area 
Perfect for Wedding and Reunions!
  • min $3,039/wk
  • max $7,596/wk
  • min $2,735/wk
  • max $6,836/wk
  • Min Stay: 3 days
Sleeps 14 people
  • 7 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $760 when you book by Oct-31-2020**
Save $492 Photo of Exclusive  Hilltop  Medieval  Villa  Features  Modern  Comforts,  Panoramic  Sea  Views,  Garden,  Pool  and  Jacuzzi  in  Pistoia,  Tuscany
  • min $2,661/wk
  • max $4,915/wk
  • min $2,395/wk
  • max $4,424/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 $492 when you book by Oct-31-2020**
Save $1,270 Photo of Villa with Pool and 2 Guesthouses for a Group in Eastern Tuscany
  • min $8,439/wk
  • max $12,696/wk
  • min $7,595/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 $1,270 when you book by Oct-31-2020**
" 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 $1,276 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 Oct-31-2020**
" Pool area, kitchen, comfortable furnishings...." - Colleen
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 Oct-31-2020**
" Truly excellent. The only thing that could have been better would have been the weather...." - James
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 Oct-31-2020**
" Great experience in a spectacular villa...." - Viviane
Save $1,330 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $13,302/wk
  • min $8,192/wk
  • max $11,972/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,330 when you book by Oct-31-2020**
" 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 $1,139 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 Oct-31-2020**
" 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 $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 Oct-31-2020**
" 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 $2,499 Photo of Beautiful Hilltop Villa in Tuscany with Spectacular Views
  • min $4,621/wk
  • max $11,464/wk
  • min $2,703/wk
  • max $10,318/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 $2,499 when you book by Oct-31-2020**
" Our group cherishes relationships and therefore thoughtfulness, condsideration and a desire to serve are a valuable component of our friendships. Upon meeting Ale..." - Mark
  • Enquire for Rates
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The villa was lovely...." - Phyllis
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 Oct-31-2020**
" 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 Oct-31-2020**
" 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 $1,275 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,300/wk
  • max $4,554/wk
  • min $1,739/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 $1,275 when you book by Oct-31-2020**
" 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 $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 Oct-31-2020**
" Our stay was the highlight of our trip to Italy. ..." - Patty
 
Displaying 1 to 30 of 51 villas