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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
  • $10,026/wk
  • $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 Mar-31-2023**
" Had a great time and Rosado was very accommodating. Beautiful view great experience...." - Adam
Save $694 Photo of Beautiful Tuscan Villa with Medieval Tower near Charming Town
  • min $2,996/wk
  • max $6,939/wk
  • min $2,696/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 Mar-31-2023**
" The owner was very helpful and very informative. The grounds were lovely. ..." - JANET
  • Enquire for Rates
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • Enquire for Rates
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Enquire for Rates
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
  • Enquire for Rates
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Wonderful..." - Patti
Save $770 Photo of Private Italian Luxury Villa Near Historic Cortona
  • $7,701/wk
  • $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 Mar-31-2023**
" Great...." - Ed
  • Enquire for Rates
Sleeps 2 to 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Very good! ..." - Randy
Save $236 Photo of Villa Within Walking Distance of Cortona
  • $2,363/wk
  • $2,127/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Washing Machine
** Save up to $236 when you book by Mar-31-2023**
" 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
  • Enquire for Rates
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We enjoyed our stay at Casa Chiana. The location was very private and beautiful. Cortona was a wonderful city. Beautiful and friendly. ..." - Lisa
  • Enquire for Rates
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
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 Mar-31-2023**
Save $289 Photo of Apartment Rental in Tuscany, Cortona
  • min $2,538/wk
  • max $2,888/wk
  • min $2,284/wk
  • max $2,599/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
** Save up to $289 when you book by Mar-31-2023**
  • Enquire for Rates
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
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 Mar-31-2023**
  • Enquire for Rates
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Enquire for Rates
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Enquire for Rates
Sleeps 8 to 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
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 Mar-31-2023**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
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 Mar-31-2023**
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 Mar-31-2023**
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
  • Enquire for Rates
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Enquire for Rates
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
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 Mar-31-2023**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
  • Enquire for Rates
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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
 
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..