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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 46 villas
Save $244 Photo of Tuscan Hillside Apartment with Shared Swimming Pool
  • min $1,883/wk
  • max $2,441/wk
  • min $1,695/wk
  • max $2,197/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $244 when you book by Jun-20-2019**
Save $332 Photo of Apartment Rental in the Center of Cortona
  • max $948/wk
  • max $853/wk
  • Min Stay: 7 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $332 when you book by Jun-20-2019**
" Prefect! Everything that I had expected and much, much more!..." - Linda
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 Jun-20-2019**
Save $604 Photo of Lakeview Tuscan countryside property has pool, gardens, wine cellar!
  • min $4,025/wk
  • max $6,038/wk
  • min $3,623/wk
  • max $5,434/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $604 when you book by Jun-20-2019**
Save $244 Photo of Historic Apartment in Lush Tuscany Countryside
  • min $2,303/wk
  • max $2,443/wk
  • min $2,073/wk
  • max $2,199/wk
  • Min Stay: 3 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $244 when you book by Jun-20-2019**
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 Jun-20-2019**
" 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 $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 Jun-20-2019**
" We had a wonderful time and Ivan couldn't have been more helpful and kind...." - Anne
  • min $727/wk
  • max $948/wk
  • min $654/wk
  • max $853/wk
  • Min Stay: 7 days
Sleeps 1 to 2 people
  • 1 single bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $95 when you book by Jun-20-2019**
" It was amazing!..." - Hannah
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 Jun-20-2019**
" 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 $113 Photo of Apartment Rental in Cortona Center
  • min $839/wk
  • max $1,125/wk
  • min $755/wk
  • max $1,013/wk
  • Min Stay: 7 days
Sleeps 3 people
  • Studio and/or Loft
  • 1 bathrooms
  • Washing Machine
  • Maid Service
** Save up to $113 when you book by Jun-20-2019**
" We had great neighbours, important as we sat opposite each other outside. Inside was very dark and not much light...." - Geoff
Save $728 Photo of Rustic Cortona Countryside Villa and Cottage with Views, Pool, Near Town, Restaurants, and Train Station
  • min $5,040/wk
  • max $7,280/wk
  • min $4,536/wk
  • max $6,552/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 1 single bedrooms
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $728 when you book by Jun-20-2019**
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 Jun-20-2019**
Save $280 Photo of Villa Within Walking Distance of Cortona
  • $2,800/wk
  • $2,520/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Washing Machine
** Save up to $280 when you book by Jun-20-2019**
" 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 $130 Photo of Apartment in Center of Cortona near Shops
  • min $915/wk
  • max $1,301/wk
  • min $824/wk
  • max $1,171/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $130 when you book by Jun-20-2019**
" 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
Save $233 Photo of Charming Farmhouse with a Private Courtyard in Cortona
  • $2,334/wk
  • $2,101/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Washing Machine
** Save up to $233 when you book by Jun-20-2019**
" 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 $187 Photo of Luxury Cortona Apartment steps from town center, restaurants, cafes
  • $1,867/wk
  • $1,680/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Air Conditioning
** Save up to $187 when you book by Jun-20-2019**
" We had a wonderful week at Erminia, near Cortona. Would definitely rent this villa again...." - Julie
Save $215 Photo of Two-Bedroom Apartment with Views in Cortona’s Historic Center
  • $2,147/wk
  • $1,932/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
** Save up to $215 when you book by Jun-20-2019**
" Our overall experience was excellent. The property is beautiful and very "Italian". ..." - Thomas
Save $580 Photo of Villa with pool near Cortona
  • min $3,402/wk
  • max $5,803/wk
  • min $3,062/wk
  • max $5,223/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 $580 when you book by Jun-20-2019**
" 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 $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 Jun-20-2019**
" Extremely satisfying. Very relaxing, so peaceful and the views are spectacular. ..." - Austin
Save $189 Photo of Private Italian Cottage Located Near Historical Cortona
  • min $1,191/wk
  • max $1,891/wk
  • min $1,072/wk
  • max $1,702/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 $189 when you book by Jun-20-2019**
" Very good! ..." - Randy
Save $823 Photo of Private Italian Villa and Cottage and Located Near Historical Cortona
  • min $5,111/wk
  • max $8,226/wk
  • min $4,600/wk
  • max $7,403/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 $823 when you book by Jun-20-2019**
" 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 Jun-20-2019**
" Liked it...." - John
Save $875 Photo of Tuscan Villa with Private Pool and Cottage Near Cortona
  • min $5,600/wk
  • max $8,750/wk
  • min $5,040/wk
  • max $7,875/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $875 when you book by Jun-20-2019**
Save $580 Photo of Villa with pool near Cortona
  • min $3,402/wk
  • max $5,803/wk
  • min $3,062/wk
  • max $5,223/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 $580 when you book by Jun-20-2019**
" 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 $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 Jun-20-2019**
" 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 $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 Jun-20-2019**
" Magical and beyond anything we could have dreamed. ..." - Dottie
Save $573 Photo of Beautiful Tuscan Villa with Medieval Tower near Charming Town
  • min $1,904/wk
  • max $5,729/wk
  • min $1,714/wk
  • max $5,156/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 $573 when you book by Jun-20-2019**
" 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 $613 Photo of Villa Rental in Tuscany, Castiglion Fiorentino
  • min $3,003/wk
  • max $6,131/wk
  • min $2,703/wk
  • max $5,518/wk
  • Min Stay: 7 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
** Save up to $613 when you book by Jun-20-2019**
Save $258 Photo of Charming Cottage Near Cortona
  • min $1,974/wk
  • max $2,581/wk
  • min $1,777/wk
  • max $2,323/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $258 when you book by Jun-20-2019**
" Very relaxing, very restful and love the pool!..." - John
Save $211 Photo of Villa Rental in Tuscany, Cortona
  • min $559/wk
  • max $2,107/wk
  • min $503/wk
  • max $1,896/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $211 when you book by Jun-20-2019**
 
Displaying 1 to 30 of 46 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..