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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 36 villas
Save $333 Photo of Villa Within Walking Distance of Cortona
  • $3,325/wk
  • $2,993/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Washing Machine
** Save up to $333 when you book by Sep-30-2021**
" Wow!! What an incredibly beautiful residence! We thoroughly enjoyed our stay within the walled city of Cortona. The villa is quite beautiful and has a breathtak..." - Catherine
Save $700 Photo of Villa Rental in Tuscany, Cortona
  • $7,000/wk
  • $6,300/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 $700 when you book by Sep-30-2021**
" The villa was perfect for our group...." - Darcie
Save $205 Photo of Cozy Cortona Villa in the Countryside
  • min $1,307/wk
  • max $2,054/wk
  • min $1,176/wk
  • max $1,849/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $205 when you book by Sep-30-2021**
" Wonderful. We absolutely loved our week at the villa. The villa itself is sweet. Up the mountain from Cortona, the villa has beautiful views of the surrounding ..." - Stephen
Save $263 Photo of Charming Farmhouse with a Private Courtyard in Cortona
  • min $2,275/wk
  • max $2,625/wk
  • min $2,048/wk
  • max $2,363/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Washing Machine
** Save up to $263 when you book by Sep-30-2021**
" The overall experience was very good, however it is not for people who are not physically fit. You are either going up a steep hill or down a steep hill. It was ..." - 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-30-2021**
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
Save $193 Photo of Private Italian Cottage Located Near Historical Cortona
  • min $1,219/wk
  • max $1,934/wk
  • min $1,097/wk
  • max $1,741/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 $193 when you book by Sep-30-2021**
" Very good! ..." - Randy
Save $680 Photo of Private Italian Luxury Villa Near Historic Cortona
  • min $4,586/wk
  • max $6,804/wk
  • min $4,127/wk
  • max $6,124/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 $680 when you book by Sep-30-2021**
" Great...." - Ed
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 $391 Photo of Accommodation Cortona Tuscany
  • min $789/wk
  • max $3,911/wk
  • min $710/wk
  • max $3,520/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 $391 when you book by Sep-30-2021**
" Liked it...." - John
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-30-2021**
Save $700 Photo of Charming Villa near Cortona
  • min $5,950/wk
  • max $7,000/wk
  • min $5,355/wk
  • max $6,300/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $700 when you book by Sep-30-2021**
Save $1,547 Photo of Villa Rental in Tuscany, Cortona
  • min $10,236/wk
  • max $15,472/wk
  • min $9,212/wk
  • max $13,925/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,547 when you book by Sep-30-2021**
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-30-2021**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
Save $735 Photo of Tuscan Farmhouse with Pool within Walking Distance of Cortona
  • min $4,200/wk
  • max $7,350/wk
  • min $3,780/wk
  • max $6,615/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 $735 when you book by Sep-30-2021**
Save $630 Photo of Tuscany Farmhouse with Swimming Pool Near Cortona
  • min $5,320/wk
  • max $6,300/wk
  • min $4,788/wk
  • max $5,670/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 $630 when you book by Sep-30-2021**
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 $1,070 Photo of Welcoming Tuscan Hillside Villa with Infinity Pool
  • min $6,386/wk
  • max $10,703/wk
  • min $5,747/wk
  • max $9,633/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 $1,070 when you book by Sep-30-2021**
" Wonderful..." - Patti
Save $637 Photo of Beautiful Tuscan Villa with Medieval Tower near Charming Town
  • min $2,177/wk
  • max $6,374/wk
  • min $1,959/wk
  • max $5,737/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $637 when you book by Sep-30-2021**
" Villa Aurora exceeded our expectations for a 2 week vacation in a rustic authentic Tuscan farm house. The house itself, while dating back to the middle ages and 1..." - Katherine
Save $1,003 Photo of Villa Rental in Tuscany, Monterchi
  • min $4,042/wk
  • max $10,026/wk
  • min $3,638/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-30-2021**
" Had a great time and Rosado was very accommodating. Beautiful view great experience...." - Adam
Save $531 Photo of Villa Rental in Tuscany, Camucia
  • min $924/wk
  • max $5,312/wk
  • min $832/wk
  • max $4,781/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $531 when you book by Sep-30-2021**
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-30-2021**
" We had a wonderful time and Ivan couldn't have been more helpful and kind...." - Anne
Save $377 Photo of Villa Rental in Tuscany, Cortona
  • min $1,273/wk
  • max $3,770/wk
  • min $1,146/wk
  • max $3,393/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $377 when you book by Sep-30-2021**
Save $306 Photo of Villa Rental in Tuscany, Cortona
  • min $806/wk
  • max $3,056/wk
  • min $725/wk
  • max $2,750/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $306 when you book by Sep-30-2021**
Save $396 Photo of Villa Rental in Tuscany, Cortona
  • min $1,223/wk
  • max $3,957/wk
  • min $1,101/wk
  • max $3,561/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $396 when you book by Sep-30-2021**
Save $616 Photo of Villa Rental in Tuscany, Monterchi
  • min $3,501/wk
  • max $6,161/wk
  • min $3,151/wk
  • max $5,545/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $616 when you book by Sep-30-2021**
Save $230 Photo of Historic Apartment in Lush Tuscany Countryside
  • min $2,093/wk
  • max $2,303/wk
  • min $1,884/wk
  • max $2,073/wk
  • Min Stay: 3 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $230 when you book by Sep-30-2021**
Save $195 Photo of Tuscan Hillside Apartment with Shared Swimming Pool
  • min $1,743/wk
  • max $1,953/wk
  • min $1,569/wk
  • max $1,758/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $195 when you book by Sep-30-2021**
Save $525 Photo of Villa Rental in Tuscany, Camucia
  • $5,250/wk
  • $4,725/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $525 when you book by Sep-30-2021**
Save $728 Photo of Rustic Cortona Countryside Villa and Cottage with Views, Pool, Near Town, Restaurants, and Train Station
  • min $5,040/wk
  • max $7,280/wk
  • min $4,536/wk
  • max $6,552/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 $728 when you book by Sep-30-2021**
Save $378 Photo of Villa Rental in Tuscany, Cortona
  • min $2,800/wk
  • max $3,780/wk
  • min $2,520/wk
  • max $3,402/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $378 when you book by Sep-30-2021**
 
Displaying 1 to 30 of 36 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..