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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 37 villas
  • min $1,587/wk
  • max $1,867/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Air Conditioning
  • min $2,941/wk
  • max $3,754/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
  • min $2,218/wk
  • max $2,635/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $839/wk
  • max $1,125/wk
  • Min Stay: 7 days
Sleeps 3 people
  • Studio and/or Loft
  • 1 bathrooms
  • Washing Machine
  • Maid Service
" We had great neighbours, important as we sat opposite each other outside. Inside was very dark and not much light...." - Geoff
  • min $727/wk
  • max $948/wk
  • Min Stay: 7 days
Sleeps 1 to 2 people
  • 1 single bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" It was amazing!..." - Hannah
  • min $1,307/wk
  • max $2,054/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" 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
  • $2,450/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Washing Machine
" We had a wonderful time and Ivan couldn't have been more helpful and kind...." - Anne
  • min $1,214/wk
  • max $1,774/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" Very good. ..." - Ralph
  • min $1,307/wk
  • max $1,895/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" 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
  • min $3,402/wk
  • max $5,803/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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
  • min $729/wk
  • max $3,416/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
" Liked it...." - John
  • min $1,680/wk
  • max $2,730/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" This villa was a wonderful setting for spending a week in Tuscany. It was comfortable for 4 of us. There was another bedroom, which would have worked well for chi..." - Rebecca
  • min $3,500/wk
  • max $4,900/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
" Magical and beyond anything we could have dreamed. ..." - Dottie
  • min $1,191/wk
  • max $1,891/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
" Very positive experience - good location, beautiful surroundings, welcoming keyholder and owners...." - Robert
  • min $2,987/wk
  • max $3,360/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Washing Machine
" 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
  • min $5,250/wk
  • max $7,000/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $1,191/wk
  • max $1,891/wk
  • Min Stay: 7 days
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
  • min $3,402/wk
  • max $5,803/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Lovely property with beautiful views. The owner was very nice and helpful. We used his cook, Ada, one night and that was fabulous. ..." - Joyce
  • min $4,760/wk
  • max $7,140/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
  • min $4,061/wk
  • max $6,651/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Great...." - Ed
  • min $915/wk
  • max $1,301/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We had a lovely time in the apartment and in Cortona. The property was comfortable, clean, and furnished nicely. The streets are steep in Cortona, so it's a bi..." - Linda
  • min $5,600/wk
  • max $7,070/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
  • min $1,960/wk
  • max $2,334/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Washing Machine
" 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
  • min $6,160/wk
  • max $9,625/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" We spent 2 very nice weeks there. The house is very nice and well taken care of; the care taker is very responsive and helpful. We would definitely recommend it...." - Luis
  • min $1,904/wk
  • max $5,390/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Excellent , exceptional!!..." - Kristi
  • min $4,691/wk
  • max $7,981/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
" 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
  • min $2,604/wk
  • max $4,690/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $3,003/wk
  • max $4,480/wk
  • Min Stay: 7 days
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
  • min $5,600/wk
  • max $8,575/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • min $3,276/wk
  • max $6,982/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Casa Toscana was exactly as described and absolutely perfect for a romantic Tuscan holiday for the two of us. Our friends joined us for one evening and kept saying..." - Nat
 
Displaying 1 to 30 of 37 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. View our Tuscany Villas in South Arezzo..