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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 42 villas
Save $221 Photo of Villa Rental in Tuscany, Cortona
  • min $587/wk
  • max $2,212/wk
  • min $528/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 Dec-10-2019**
Save $718 Photo of Lakeview Tuscan countryside property has pool, gardens, wine cellar!
  • min $5,250/wk
  • max $7,175/wk
  • min $4,725/wk
  • max $6,458/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $718 when you book by Dec-10-2019**
Save $518 Photo of Villa with pool near Cortona
  • min $3,402/wk
  • max $5,180/wk
  • min $3,062/wk
  • max $4,662/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 $518 when you book by Dec-10-2019**
" 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 $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 Dec-10-2019**
" 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 $273 Photo of Villa Rental Very Close to Cortona
  • min $1,680/wk
  • max $2,730/wk
  • min $1,512/wk
  • max $2,457/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $273 when you book by Dec-10-2019**
" We all had an absolutely fabulous time. The villa was delightful , even better than I had hoped . It was extremely comfortable , full of atmosphere and in a gre..." - Julianne
Save $824 Photo of Private Italian Villa and Cottage and Located Near Historical Cortona
  • min $5,111/wk
  • max $8,235/wk
  • min $4,600/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 Dec-10-2019**
" 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 $342 Photo of Accommodation Cortona Tuscany
  • min $729/wk
  • max $3,416/wk
  • min $656/wk
  • max $3,074/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 $342 when you book by Dec-10-2019**
" Liked it...." - John
Save $781 Photo of Villa Within Walking Distance of Cortona
  • $3,325/wk
  • $2,544/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Washing Machine
** Save up to $781 when you book by Dec-10-2019**
" 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 $434 Photo of Villa Rental in Tuscany, Camucia
  • min $813/wk
  • max $4,343/wk
  • min $732/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 Dec-10-2019**
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 Dec-10-2019**
Save $546 Photo of Beautiful Tuscan Villa with Medieval Tower near Charming Town
  • min $1,904/wk
  • max $5,460/wk
  • min $1,714/wk
  • max $4,914/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $546 when you book by Dec-10-2019**
" 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 $735 Photo of Charming Farmhouse with a Private Courtyard in Cortona
  • min $2,275/wk
  • max $2,625/wk
  • min $1,638/wk
  • max $1,890/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Washing Machine
** Save up to $735 when you book by Dec-10-2019**
" 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 $193 Photo of Private Italian Cottage Located Near Historical Cortona
  • min $1,191/wk
  • max $1,934/wk
  • min $1,072/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 Dec-10-2019**
" Very good! ..." - Randy
Save $469 Photo of Small Charming Stone Villa near Cortona
  • min $2,604/wk
  • max $4,690/wk
  • min $2,344/wk
  • max $4,221/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 $469 when you book by Dec-10-2019**
Save $189 Photo of Tuscan House Near Cortona
  • min $1,191/wk
  • max $1,891/wk
  • min $1,072/wk
  • max $1,702/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Washing Machine
  • Maid Service
** Save up to $189 when you book by Dec-10-2019**
" 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 $588 Photo of Two-Bedroom Apartment with Views in Cortona’s Historic Center
  • min $1,838/wk
  • max $2,100/wk
  • min $1,323/wk
  • max $1,512/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
** Save up to $588 when you book by Dec-10-2019**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
Save $630 Photo of Villa with pool near Cortona
  • min $3,402/wk
  • max $6,300/wk
  • min $3,062/wk
  • max $5,670/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 $630 when you book by Dec-10-2019**
" 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 $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 Dec-10-2019**
" 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 Dec-10-2019**
" Exceeded expectations and resulted in a magical experience overall...." - John
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 Dec-10-2019**
" Great...." - Ed
Save $560 Photo of Villa Rental in Tuscany, Cortona
  • min $4,620/wk
  • max $5,600/wk
  • min $4,158/wk
  • max $5,040/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $560 when you book by Dec-10-2019**
Save $630 Photo of Tuscany Farmhouse with Swimming Pool Near Cortona
  • min $4,200/wk
  • max $6,300/wk
  • min $3,780/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 Dec-10-2019**
Save $997 Photo of Welcoming Tuscan Hillside Villa with Infinity Pool
  • min $6,386/wk
  • max $9,974/wk
  • min $5,747/wk
  • max $8,977/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 $997 when you book by Dec-10-2019**
" Wonderful..." - Patti
Save $490 Photo of Villa Near Cortona with a Private Pool
  • min $3,003/wk
  • max $4,900/wk
  • min $2,703/wk
  • max $4,410/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 $490 when you book by Dec-10-2019**
" 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 $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 Dec-10-2019**
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 Dec-10-2019**
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 Dec-10-2019**
" We had a wonderful time and Ivan couldn't have been more helpful and kind...." - Anne
Save $378 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • min $3,500/wk
  • max $3,780/wk
  • min $3,150/wk
  • max $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 Dec-10-2019**
" We had a wonderful experience at this villa. Great views and neighborhood...." - Kathy
Save $375 Photo of Villa with Pool Near Cortona in the Valdichiana
  • min $2,941/wk
  • max $3,754/wk
  • min $2,647/wk
  • max $3,379/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 $375 when you book by Dec-10-2019**
" 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 Dec-10-2019**
" Magical and beyond anything we could have dreamed. ..." - Dottie
 
Displaying 1 to 30 of 42 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..