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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 >

Showing 1 to 30 of 39 properties
  • min $1,925/wk
  • max $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 $1,191/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
" Very peaceful with beautiful views. A great base for touring Tuscany. Our hosts were wonderful. A wonderful conversion of the old mill into a residence...." - Dennis
  • 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
" This property was exactly as described on the website. ..." - Cheryl Tvl Agent
  • min $1,225/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
" It was PURE HEAVEN!!! ..." - Jean
  • min $2,918/wk
  • max $5,179/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
  • 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
" Wonderful stay in a beautiful area with plenty of great areas to explore...." - Michael
  • 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 $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 $1,246/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 $3,811/wk
  • max $6,361/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
Save $600 Photo of Large Stone Farmhouse in the Hills Near Cortona
  • min $3,090/wk
  • max $4,615/wk
  • min $2,688/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $600 when you book by Oct-31-2017**
  • min $3,811/wk
  • max $6,361/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 $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 $5,256/wk
  • max $7,769/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 $6,138/wk
  • max $7,693/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 $4,061/wk
  • max $5,951/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 $4,691/wk
  • max $7,281/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 $1,191/wk
  • max $1,751/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
  • min $1,960/wk
  • max $2,450/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 $2,667/wk
  • max $3,360/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Washing Machine
" This was an amazing villa dating back to the 1200s. It is beautifully maintained, offers a great central meeting space and living area, and large, private bedroom ..." - Mary-ann
  • min $4,522/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
" Just a beautiful and peaceful place, great pool, magnificent view. Would go back in a heartbeat!..." - ROBERT
  • min $3,365/wk
  • max $4,947/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
  • $7,616/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
" Exceeded expectations and resulted in a magical experience overall...." - John
  • min $3,360/wk
  • max $5,740/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
  • min $1,680/wk
  • max $2,058/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • min $4,004/wk
  • max $5,712/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" My wife and I have been to Italy more than 20 times, and we have never had a more genuinely Italian experience than at this villa...." - Alexander
  • $5,217/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" Absolutely wonderful Tuscan experience...." - Mike
  • min $1,974/wk
  • max $2,581/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Very relaxing, very restful and love the pool!..." - John
  • min $2,941/wk
  • max $3,264/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 $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
 
Showing 1 to 30 of 39 properties

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..