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Featured Holiday Homes in Cortona

Casa Fontelunga, Tuscan holiday villa with private pool

Casa Fontelunga, Tuscan holiday villa with private pool

cortona
Located in Cortona, this vacation home is in a rural location, within a 15-minute drive of Santa Maria delle Grazie and Cortona Cathedral.
Casa Fontelunga, Tuscan holiday villa with private pool
Podere Casorbica with free parking, large garden, private pool.

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

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 5 minutes from Cortona Cathedral.
Podere Casorbica with free parking, large garden, private pool.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Cortona
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be within a 15-minute drive of Lake Trasimeno and Cortona Cathedral.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
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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
With a stay at this vacation home in Cortona, you'll be in the mountains, and 18.4 mi (29.6 km) from Lake Trasimeno and 6.9 mi (11.1 km) from Villa ...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
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
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be within a 5-minute walk of Signorelli Theatre and Piazza della Repubblica.
Casa Bacco - private house with a remarkable garden in the centre of Cortona
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
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be steps from 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
Located in Cortona, this vacation home is in the mountains, within a 15-minute drive of Villa Bramasole and Casali Palace.
beautiful tuscan villa with pool, ideal for groups
Small stone farmhouse overlooking Cortona with private pool and garden

Small stone farmhouse overlooking Cortona with private pool and garden

Cortona
Located in Cortona, this vacation home is in a rural location, within a 15-minute drive of Santa Maria delle Grazie and Cortona Cathedral.
Small stone farmhouse overlooking Cortona with private pool and garden
La Pergola typical Tuscan house with wonderful view

La Pergola typical Tuscan house with wonderful view

Arezzo
A stay at this vacation home places you in the heart of Cortona, within a 15-minute walk of Villa Bramasole and Santa Margherita Basilica.
La Pergola typical Tuscan house with wonderful view
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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
237 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$806
Popular accommodation
Casa Fontelunga, Tuscan holiday villa with private pool, Podere Casorbica with free parking, large garden, private pool., Casa delle Rose: charming house with stunning balcony in the heart of Cortona, La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno , Casa Bacco - private house with a remarkable garden in the centre of Cortona, Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream" , beautiful tuscan villa with pool, ideal for groups, Small stone farmhouse overlooking Cortona with private pool and garden, La Pergola typical Tuscan house with wonderful view

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
Fully refundableReserve now, pay when you stay
The price is AU$806 per night from 1 Apr to 2 Apr
AU$806
includes taxes & fees
1 Apr - 2 Apr
When you stay at Villa di Piazzano - Small Luxury Hotel of the World in Cortona, you'll be in the historical district and 7.6 mi (12.2 km) from Lake ...
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
Fully refundableReserve now, pay when you stay
The price is AU$555 per night from 27 Apr to 28 Apr
AU$555
includes taxes & fees
27 Apr - 28 Apr
A stay at Monastero di Cortona Hotel & Spa places you in the heart of Cortona, within a 5-minute walk of Signorelli Theatre and Museum of the Etruscan ...
Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is AU$717 per night from 9 Apr to 10 Apr
AU$717
includes taxes & fees
9 Apr - 10 Apr
Located in Cortona, Il Falconiere - Relais e Chateaux is in a rural location, within a 15-minute drive of Museum of the Etruscan Academy and Villa ...
Il Falconiere - Relais e Chateaux
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Hotel San Luca

Hotel San Luca

4 out of 5
Piazza Garibaldi 1, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 2 Apr to 3 Apr
AU$163
includes taxes & fees
2 Apr - 3 Apr
A stay at Hotel San Luca places you in the heart of Cortona, steps from Giuseppe Garibaldi Memorial and San Domenico Church.
Hotel San Luca
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See all available properties in Cortona
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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.