Book Holiday Homes in Cortona

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

Podere Casorbica with free parking, large garden, 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 Giuseppe Garibaldi Memorial ...
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
Stay at this vacation home in Cortona. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Piazza della Repubblica and Casali Palace ...
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
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
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
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 Casali Palace ...
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
Small stone farmhouse overlooking Cortona with private pool and garden

Small stone farmhouse overlooking Cortona with private pool and garden

Cortona
Stay at this vacation home in Cortona. Enjoy private pools, a garden, and patios. Popular attractions Eremo Le Celle and Santa Maria Nuova are located ...
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
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
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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
NZ$172
Highest Price
NZ$889
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 NZ$889 per night from 8 Apr to 9 Apr
NZ$889
includes taxes & fees
8 Apr - 9 Apr
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
Fully refundableReserve now, pay when you stay
The price is NZ$667 per night from 16 Apr to 17 Apr
NZ$667
includes taxes & fees
16 Apr - 17 Apr
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
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 NZ$823 per night from 16 Apr to 17 Apr
NZ$823
includes taxes & fees
16 Apr - 17 Apr
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 ...
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 NZ$172 per night from 7 Apr to 8 Apr
NZ$172
includes taxes & fees
7 Apr - 8 Apr
Stay at this 4-star hotel in Cortona. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Giuseppe Garibaldi Memorial and San Domenico ...
Hotel San Luca
Don't see what you're looking for?
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.