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South Arezzo Villas and Vacation Rentals

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 31 to 60 of 43 villas
Save $378 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • $3,780/wk
  • $3,402/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 $378 when you book by Mar-31-2019**
" It was wonderful. It is very comfortable and the views are magnificent. The landscaping is well done and interesting...." - Richard
Save $714 Photo of Tuscany Farmhouse with Swimming Pool Near Cortona
  • min $4,760/wk
  • max $7,140/wk
  • min $4,284/wk
  • max $6,426/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 $714 when you book by Mar-31-2019**
Save $448 Photo of Villa Near Cortona with a Private Pool
  • min $3,003/wk
  • max $4,480/wk
  • min $2,703/wk
  • max $4,032/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 $448 when you book by Mar-31-2019**
" 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 $680 Photo of Private Italian Luxury Villa Near Historic Cortona
  • min $4,481/wk
  • max $6,804/wk
  • min $4,033/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 Mar-31-2019**
" Great...." - Ed
Save $641 Photo of Farmhouse in Tuscany with Five Bedrooms and Bathrooms near Cortona
  • min $4,004/wk
  • max $6,407/wk
  • min $3,604/wk
  • max $5,766/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 $641 when you book by Mar-31-2019**
" A dream come true!..." - Angela
Save $700 Photo of Villa with pool near Cortona
  • $7,000/wk
  • $6,300/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $700 when you book by Mar-31-2019**
" Exceeded expectations and resulted in a magical experience overall...." - John
Save $574 Photo of Charming Villa near Cortona
  • min $3,360/wk
  • max $5,740/wk
  • min $3,024/wk
  • max $5,166/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $574 when you book by Mar-31-2019**
Save $707 Photo of Tuscan Farmhouse with Pool within Walking Distance of Cortona
  • min $5,600/wk
  • max $7,070/wk
  • min $5,040/wk
  • max $6,363/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 $707 when you book by Mar-31-2019**
Save $630 Photo of Villa Rental in Tuscany, Cortona
  • min $4,620/wk
  • max $6,300/wk
  • min $4,158/wk
  • max $5,670/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $630 when you book by Mar-31-2019**
Save $510 Photo of Charming Tuscan Farmhouse Walking Distance to Cortona
  • min $3,276/wk
  • max $5,096/wk
  • min $2,948/wk
  • max $4,586/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $510 when you book by Mar-31-2019**
" It was a lovely house for just the two of us to stay in...." - Ian
Save $177 Photo of Tuscany Accommodation
  • min $1,214/wk
  • max $1,774/wk
  • min $1,093/wk
  • max $1,597/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $177 when you book by Mar-31-2019**
" Very good. ..." - Ralph
Save $187 Photo of Luxury Cortona Apartment steps from town center, restaurants, cafes
  • min $1,774/wk
  • max $1,867/wk
  • min $1,597/wk
  • max $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-31-2019**
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
Save $205 Photo of Tuscan Apartment with Shared Pool and Breathtaking Views of Cortona
  • min $1,307/wk
  • max $2,054/wk
  • min $1,176/wk
  • max $1,849/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $205 when you book by Mar-31-2019**
" We had a great time. Vanessa was marvelous and always very sweet and helpful. We felt very cozy in our unit. It was located centrally to most of Tuscany, and Umbr..." - Craig
 
Displaying 31 to 60 of 43 villas

Show all 57 Villas and Houses for Rent in Arezzo

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..