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Villa Rentals in Tuscany South of Arezzo

Located in the southern reaches of the Arezzo province, the countryside around Cortona offers many opportunities for exploration and discovery. Whether staying in a Tuscan villa near Loro Ciuffenna, Montisi, Cicogna, or Bettolle, you can head to Cortona for a day of museum hopping, or venture further south to the towns of northern Umbria and Lake Trasimeno.   Continue >

Displaying 1 to 30 of 35 villas
Save $1,003 Photo of Villa Rental in Tuscany, Monterchi
  • min $4,353/wk
  • max $10,026/wk
  • min $3,918/wk
  • max $9,023/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 $1,003 when you book by Sep-30-2022**
" Had a great time and Rosado was very accommodating. Beautiful view great experience...." - Adam
Save $333 Photo of Villa Within Walking Distance of Cortona
  • min $2,363/wk
  • max $3,325/wk
  • min $2,127/wk
  • max $2,993/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Washing Machine
** Save up to $333 when you book by Sep-30-2022**
" We had a great experience. The steep walk to and from the villa was challenging at times. I missed not having a car to go to other areas . ..." - Kathryn
Save $1,400 Photo of Villa with Pool Near Cortona in the Valdichiana
  • $4,376/wk
  • $3,938/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 $1,400 when you book by Sep-30-2022**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
  • min $2,275/wk
  • max $2,625/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Washing Machine
" The overall experience was very good...." - Ellen
Save $187 Photo of Luxury Cortona Apartment steps from town center, restaurants, cafes
  • $1,867/wk
  • $1,680/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Air Conditioning
** Save up to $187 when you book by Sep-30-2022**
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
Save $476 Photo of Villa Rental in Tuscany, Cortona
  • $4,760/wk
  • $4,284/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $476 when you book by Sep-30-2022**
Save $1,757 Photo of Villa Rental in Tuscany, Cortona
  • min $10,236/wk
  • max $17,573/wk
  • min $9,212/wk
  • max $15,816/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,757 when you book by Sep-30-2022**
Save $588 Photo of Tuscan Farmhouse with Pool within Walking Distance of Cortona
  • $5,880/wk
  • $5,292/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $588 when you book by Sep-30-2022**
Save $266 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • min $2,380/wk
  • max $2,660/wk
  • min $2,142/wk
  • max $2,394/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 $266 when you book by Sep-30-2022**
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
Save $525 Photo of Villa Near Cortona with a Private Pool
  • $5,250/wk
  • $4,725/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 $525 when you book by Sep-30-2022**
" 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 $908 Photo of Private Italian Villa and Cottage and Located Near Historical Cortona
  • min $5,986/wk
  • max $9,084/wk
  • min $5,387/wk
  • max $8,176/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $908 when you book by Sep-30-2022**
" By far the best property we have ever rented in Italy over the past 10 years. Maybe the best villa we've rented anywhere!..." - Karen
Save $770 Photo of Private Italian Luxury Villa Near Historic Cortona
  • min $4,709/wk
  • max $7,701/wk
  • min $4,238/wk
  • max $6,931/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $770 when you book by Sep-30-2022**
" Great...." - Ed
Save $595 Photo of Charming Villa near Cortona
  • $5,950/wk
  • $5,355/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $595 when you book by Sep-30-2022**
Save $694 Photo of Beautiful Tuscan Villa with Medieval Tower near Charming Town
  • min $2,208/wk
  • max $6,939/wk
  • min $1,987/wk
  • max $6,245/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $694 when you book by Sep-30-2022**
" The owner was very helpful and very informative. The grounds were lovely. ..." - JANET
Save $532 Photo of Villa Rental in Tuscany, Camucia
  • $5,320/wk
  • $4,788/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $532 when you book by Sep-30-2022**
Save $532 Photo of Tuscany Farmhouse with Swimming Pool Near Cortona
  • $5,320/wk
  • $4,788/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $532 when you book by Sep-30-2022**
Save $685 Photo of Welcoming Tuscan Hillside Villa with Infinity Pool
  • $6,853/wk
  • $6,168/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $685 when you book by Sep-30-2022**
" Wonderful..." - Patti
Save $370 Photo of Accommodation Cortona Tuscany
  • min $789/wk
  • max $3,695/wk
  • min $710/wk
  • max $3,326/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $370 when you book by Sep-30-2022**
" We enjoyed our stay at Casa Chiana. The location was very private and beautiful. Cortona was a wonderful city. Beautiful and friendly. ..." - Lisa
Save $245 Photo of Apartment Overlooking the Rooftops of the Ancient Town of Cortona
  • $2,450/wk
  • $2,205/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Washing Machine
** Save up to $245 when you book by Sep-30-2022**
" We had a wonderful time and Ivan couldn't have been more helpful and kind...." - Anne
Save $140 Photo of Villa Rental in Tuscany, Cortona
  • min $886/wk
  • max $1,400/wk
  • min $797/wk
  • max $1,260/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $140 when you book by Sep-30-2022**
Save $3,030 Photo of Villa Rental in Tuscany, Camucia
  • min $958/wk
  • max $4,933/wk
  • min $862/wk
  • max $4,440/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,030 when you book by Sep-30-2022**
Save $420 Photo of Villa Rental in Tuscany, Cortona
  • min $2,975/wk
  • max $4,200/wk
  • min $2,678/wk
  • max $3,780/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $420 when you book by Sep-30-2022**
Save $683 Photo of Rustic Cortona Countryside Villa and Cottage with Views, Pool, Near Town, Restaurants, and Train Station
  • min $4,725/wk
  • max $6,825/wk
  • min $4,253/wk
  • max $6,143/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $683 when you book by Sep-30-2022**
Save $595 Photo of Villa Rental in Tuscany, Cortona
  • $5,950/wk
  • $5,355/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $595 when you book by Sep-30-2022**
" The villa was perfect for our group...." - Darcie
Save $630 Photo of Villa Rental in Tuscany, Cortona
  • min $4,288/wk
  • max $6,300/wk
  • min $3,859/wk
  • max $5,670/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $630 when you book by Sep-30-2022**
Save $207 Photo of Private Italian Cottage Located Near Historical Cortona
  • min $1,279/wk
  • max $2,074/wk
  • min $1,151/wk
  • max $1,867/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $207 when you book by Sep-30-2022**
" Very good! ..." - Randy
Save $190 Photo of Apartment Rental in Tuscany, Monte Benichi
  • min $1,756/wk
  • max $1,903/wk
  • min $1,580/wk
  • max $1,713/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $190 when you book by Sep-30-2022**
Save $345 Photo of Villa Rental in Tuscany, Cortona
  • min $2,824/wk
  • max $3,453/wk
  • min $2,542/wk
  • max $3,108/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $345 when you book by Sep-30-2022**
Save $210 Photo of Two-Bedroom Apartment with Views in Cortona’s Historic Center
  • min $1,838/wk
  • max $2,100/wk
  • min $1,654/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
** Save up to $210 when you book by Sep-30-2022**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
Save $209 Photo of Tuscan Hillside Apartment with Shared Swimming Pool
  • min $1,883/wk
  • max $2,093/wk
  • min $1,695/wk
  • max $1,884/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $209 when you book by Sep-30-2022**
 
Displaying 1 to 30 of 35 villas

Perched on a mountainside, Cortona is a medieval city with sweeping views over the Valdichiana. Originally one of the 12 cities that formed the Etruscan confederation, a portion of the city's 4th century BC walls remain preserved. Etruscan tombs and an altar can be viewed at excavation sites called Melone I and II; additional artifacts can be viewed in the Museo dell'Accademia Etrusca. Renaissance aficionados should pay a visit to the Museo Diocesano, which houses works by such masters as Lorenzetti and Fra Angelico..