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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 61 properties
  • min $3,555/wk
  • max $5,530/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" We loved our experience!! It was so much more than we ever imagined it could be!..." - Valerie
  • min $498/wk
  • max $854/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Good...." - John
  • min $948/wk
  • max $1,517/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
" Outstanding! Overall, we considered this to be the best of a number of holiday rentals that we have enjoyed...." - David
  • min $735/wk
  • max $1,246/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Everything was great. The owners were so nice! The daughter spoke very good English. Would recommend the spot to anyone... the history of the area is fantastic. ..." - CLARA
  • min $901/wk
  • max $1,565/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Our experience was just fine. The property was very comfortable and clean. We had everything with which to work. The views from the property were beautiful...." - John
  • min $1,541/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Very satisfying..." - Magdalena
  • min $1,391/wk
  • max $1,644/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The apartment was great and we really enjoyed living there for a week. The property manager was absolutely great, doing everything she could to make the experienc..." - Cedric
  • min $1,580/wk
  • max $1,975/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Washing Machine
" We had a great time! Ivan was a very welcoming host and we enjoyed learning about the history of the 2000 year old house and its evolution. ..." - Greg
  • min $1,738/wk
  • max $2,844/wk
  • min $1,564/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $174 when you book by Sep-30-2010**
" A really amazing place - the photos do not do it justice. We loved the grounds, the home was enormous and well appointed, and the whole experience very special. We..." - Jon
  • min $3,371/wk
  • max $4,938/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" Vista Infinita was a perfect spot for our family. Easy walking distance to the town of Cortona 10 minutes, a great pool, and an incredible view of the valley and l..." - Chris
  • min $1,738/wk
  • max $2,844/wk
  • min $1,564/wk
  • max $2,560/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $284 when you book by Sep-30-2010**
" Overall experience was good. Enjoyed picking fresh cherries from the cherry tree and swimming in the pool with the kids. ..." - Jon
  • min $1,625/wk
  • max $2,726/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
" The view, the pool and yard. We spent most afternoons relaxing in the pool. It is small but with the jets it was very very nice!! The kitchen was very well sup..." - John Suzanne
  • min $1,492/wk
  • max $2,280/wk
  • min $1,343/wk
  • max $2,052/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $228 when you book by Sep-30-2010**
" We loved this place and would return in a heartbeat! ..." - Carol
  • min $1,930/wk
  • max $4,096/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $948/wk
  • max $1,159/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,422/wk
  • max $2,212/wk
  • min $1,280/wk
  • max $1,991/wk
  • Min Stay: 7 days
Sleeps 3 to 6 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Sep-30-2010**
  • min $1,707/wk
  • max $2,844/wk
  • Min Stay: 7 days
Sleeps 5 to 8 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • min $1,141/wk
  • max $1,579/wk
  • min $1,027/wk
  • max $1,421/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $158 when you book by Sep-30-2010**
  • min $5,728/wk
  • max $7,308/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
  • min $4,938/wk
  • max $5,925/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • min $1,738/wk
  • max $2,844/wk
  • min $1,564/wk
  • max $2,560/wk
  • Min Stay: 7 days
Sleeps 4 to 7 people
  • 2 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $284 when you book by Sep-30-2010**
" We had a lovely time at the apartment near Cortona. The unit had plenty of room for 6. We loved the property and would highly recommend it. ..." - Andrew
  • min $711/wk
  • max $948/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
" loved Cortona and this location. The apartment was small but charming...." - Roxie
  • min $2,370/wk
  • max $4,266/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" It was a terrific experience. The house and location were even better than expected...." - Robert
  • min $3,635/wk
  • max $5,706/wk
  • max $5,135/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $571 when you book by Sep-30-2010**
" Wonderful, above expectations. A really great property. We all agreed that the listing you have for this Villa did not do justice to it. It is a spectacular Villa,..." - Tom
  • min $2,371/wk
  • max $3,951/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $325 when you book by Sep-30-2010**
  • min $1,317/wk
  • max $1,930/wk
  • min $1,185/wk
  • max $1,737/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $193 when you book by Sep-30-2010**
" Very good, the property is well located, very well maintained and the all family are extremely friendly and helpful...." - Anthony
  • min $711/wk
  • max $948/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • min $1,141/wk
  • max $1,579/wk
  • min $1,027/wk
  • max $1,421/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $158 when you book by Sep-30-2010**
" The place and ambience were great. The hosts are great and the location fun...." - Rick
  • min $3,556/wk
  • max $4,109/wk
  • Min Stay: 7 days
Sleeps 12 to 14 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" The villa was perfect for our group...." - Darcie
  • min $2,528/wk
  • max $3,055/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
 
Showing 1 to 30 of 61 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..