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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 41 villas
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 Aug-10-2021**
Save $248 Photo of House Rental in Tuscany, Camucia
  • min $530/wk
  • max $2,478/wk
  • min $477/wk
  • max $2,230/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $248 when you book by Aug-10-2021**
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 Aug-10-2021**
" Great...." - Ed
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 Aug-10-2021**
" 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
  • $2,625/wk
  • $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 Aug-10-2021**
" 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 $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 Aug-10-2021**
" 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 $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 Aug-10-2021**
" Liked it...." - John
Save $560 Photo of Villa with pool near Cortona
  • min $4,200/wk
  • max $5,600/wk
  • min $3,780/wk
  • max $5,040/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 $560 when you book by Aug-10-2021**
" Three couples shared Villa Ilia - it was a perfect place to stay. The owner was an excellent host. He was waiting for us when we arrived at the meeting point and ..." - Lynn
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 Aug-10-2021**
" Wonderful..." - Patti
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 Aug-10-2021**
Save $560 Photo of Villa Rental in Tuscany, Cortona
  • min $4,760/wk
  • max $5,600/wk
  • min $4,284/wk
  • max $5,040/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $560 when you book by Aug-10-2021**
Save $560 Photo of Villa with pool near Cortona
  • $5,600/wk
  • $5,040/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 $560 when you book by Aug-10-2021**
" Lovely property with beautiful views. The owner was very nice and helpful. We used his cook, Ada, one night and that was fabulous. ..." - Joyce
Save $630 Photo of Villa Rental in Tuscany, Cortona
  • min $4,200/wk
  • max $6,300/wk
  • min $3,780/wk
  • max $5,670/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $630 when you book by Aug-10-2021**
Save $434 Photo of Villa Rental in Tuscany, Camucia
  • min $854/wk
  • max $4,343/wk
  • min $769/wk
  • max $3,909/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $434 when you book by Aug-10-2021**
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 Aug-10-2021**
" Very good! ..." - Randy
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 Aug-10-2021**
Save $210 Photo of Two-Bedroom Apartment with Views in Cortona’s Historic Center
  • $2,100/wk
  • $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 Aug-10-2021**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
Save $403 Photo of Villa with Pool Near Cortona in the Valdichiana
  • $4,026/wk
  • $3,623/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 $403 when you book by Aug-10-2021**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
Save $490 Photo of Beautiful Villa in Tuscany Close to Cortona
  • min $3,500/wk
  • max $4,900/wk
  • min $3,150/wk
  • max $4,410/wk
  • Min Stay: 7 days
Sleeps 10 to 13 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $490 when you book by Aug-10-2021**
" Magical and beyond anything we could have dreamed. ..." - Dottie
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 Aug-10-2021**
" 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 $560 Photo of Villa with pool near Cortona
  • $5,600/wk
  • $5,040/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 $560 when you book by Aug-10-2021**
" Exceeded expectations and resulted in a magical experience overall...." - John
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 Aug-10-2021**
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 Aug-10-2021**
  • Enquire for Rates
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
" This was a fabulous experience! The villa was very charming and perfect for our week's stay - lots of room and great kitchen for our cooking experiences. Loc..." - Susan
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 Aug-10-2021**
" It was amazing. The views, the amenities and of course, the villa owner. He had tours we scheduled with him that are memories we will cherish for the rest of our..." - Marjorie
Save $770 Photo of Villa Rental in Tuscany, Cortona
  • min $6,580/wk
  • max $7,700/wk
  • min $5,922/wk
  • max $6,930/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $770 when you book by Aug-10-2021**
Save $221 Photo of Villa Rental in Tuscany, Cortona
  • min $700/wk
  • max $2,212/wk
  • min $630/wk
  • max $1,991/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Aug-10-2021**
  • $1,867/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Air Conditioning
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
Save $824 Photo of Private Italian Villa and Cottage and Located Near Historical Cortona
  • min $5,227/wk
  • max $8,235/wk
  • min $4,704/wk
  • max $7,412/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 $824 when you book by Aug-10-2021**
" 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 $735 Photo of Villa Rental in Tuscany, Monterchi
  • min $3,501/wk
  • max $7,351/wk
  • min $3,151/wk
  • max $6,616/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $735 when you book by Aug-10-2021**
 
Displaying 1 to 30 of 41 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..