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Featured Holiday Homes in Cortona

Podere Casorbica with free parking, large garden, swimming pool.

Podere Casorbica with free parking, large garden, swimming pool.

cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, private pools, and a garden. Popular attractions Santa Maria delle Grazie and Giuseppe Garibaldi Memorial ...
Podere Casorbica with free parking, large garden, swimming pool.
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

Cortona
Book a stay at this family-friendly vacation home in Cortona. Enjoy free WiFi, a garden, and patios. Popular attractions Eremo Le Celle and Villa Bramasole are ...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
Nice house in the country of Cortona.

Nice house in the country of Cortona.

Cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Santa Maria delle Grazie and Piazza della Repubblica ...
Nice house in the country of Cortona.
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Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona
Stay at this vacation home in Cortona. Enjoy tennis courts, patios, and cable/satellite TV service. Popular attractions Piazza della Repubblica and Palazzo Comunale ...
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
beautiful tuscan villa with pool, ideal for groups

beautiful tuscan villa with pool, ideal for groups

Cortona
Book a stay at this family-friendly vacation home in Cortona. Enjoy free WiFi, private pools, and a garden. Popular attractions Eremo Le Celle and Villa Bramasole ...
beautiful tuscan villa with pool, ideal for groups
Casa Fontelunga, Tuscan holiday villa with private pool

Casa Fontelunga, Tuscan holiday villa with private pool

cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, private pools, and a garden. Popular attractions Santa Maria delle Grazie and Villa Bramasole are located ...
Casa Fontelunga, Tuscan holiday villa with private pool
Casa Bacco - private house with a remarkable garden in the centre of Cortona

Casa Bacco - private house with a remarkable garden in the centre of Cortona

Cortona
Stay at this vacation home in Cortona. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Signorelli Theatre and Museum ...
Casa Bacco - private house with a remarkable garden in the centre of Cortona
La Pergola typical Tuscan house with wonderful view

La Pergola typical Tuscan house with wonderful view

Arezzo
Stay at this vacation home in Cortona. Enjoy free WiFi, a garden, and patios. Popular attractions Villa Bramasole and Fortress of Girifalco are located ...
La Pergola typical Tuscan house with wonderful view
Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City

Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City

Cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Giuseppe Garibaldi Memorial and San Domenico ...
Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cortona Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cortona vacation homes are the perfect way for you to wing it.

Holiday houses in Cortona let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cortona in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cortona adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cortona with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cortona vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cortona Holiday Homes essential information

Accommodation
213 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Podere Casorbica with free parking, large garden, swimming pool., La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno , Nice house in the country of Cortona., Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream" , beautiful tuscan villa with pool, ideal for groups, Casa Fontelunga, Tuscan holiday villa with private pool, Casa Bacco - private house with a remarkable garden in the centre of Cortona, La Pergola typical Tuscan house with wonderful view, Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City

Top trending hotels in Cortona

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Stay at this 5-star luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Stay at this 5-star luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Monastero di Cortona Hotel & Spa
Borgo Il Melone

Borgo Il Melone

4 out of 5
Case Sparse, 38, Localita Il Sodo, Cortona, AR
Stay at this 4-star business-friendly hotel in Cortona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Borgo Il Melone
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Relais Il Falconiere

Relais Il Falconiere

5 out of 5
Localita San Martino 370, Cortona, AR
Stay at this 5-star luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cortona Cathedral and Museo Diocesano are ...
Relais Il Falconiere
Don't see what you're looking for?
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.