A hillside town with historic buildings, a church, and vineyards.

Cortona Holiday Rentals

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Our top choices for Cortona holiday rentals

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is NZ$281
includes taxes & fees
1 Nov - 2 Nov
B&B Piccolo Hotel

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is NZ$404
includes taxes & fees
5 Nov - 6 Nov
CASA AMBRA

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
9.8 out of 10, Exceptional, (9 reviews)
"Nice property"
United States
Joseph
The price is NZ$193
includes taxes & fees
1 Dec - 2 Dec
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

4. Cortona Shabby Chic House<br>(Independent & Balcony)

Cortona Shabby Chic House<br>(Independent & Balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is NZ$299
includes taxes & fees
30 Nov - 1 Dec
Cortona Shabby Chic House<br>(Independent & Balcony)

5. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is NZ$217
includes taxes & fees
14 Nov - 15 Nov
Vicolo Della Scala Rooms - Il Sole

6. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is NZ$131
includes taxes & fees
1 Nov - 2 Nov
Vacation home with a panoramic terrace, ideal for families and couples

7. Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome

Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome
Cortona Old Town
Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome

8. Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
The price is NZ$252
includes taxes & fees
2 Nov - 3 Nov
Casa Beppina Cortona by Interhome

9. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is NZ$178
includes taxes & fees
3 Nov - 4 Nov
Montecchio di Cortona

10. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is NZ$294
includes taxes & fees
8 Nov - 9 Nov
Cortonas Rooftop Nest

11. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveller
The price is NZ$474
includes taxes & fees
1 Nov - 2 Nov
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

12. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is NZ$12,394
includes taxes & fees
30 Nov - 1 Dec
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

13. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is NZ$236
includes taxes & fees
2 Nov - 3 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

14. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is NZ$803
includes taxes & fees
1 Dec - 2 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

15. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
Wohnung la Mimosa by Interhome

16. Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Pros: The estate is absolutely amazing. Nice buildings, charming garden, super pool with great view. Good location in Tuscany. Cons: The Italian love is gone. When we first visited (2014) there was an amazing host and personal touch. Now it’s just a business transaction, we hire a piece of property. Check-in without seeing anyone. And many little issues in the appartement. Kitchen amenities are limited, doors don’t close properly, etc. And is has been like this for years, apparently nobody...
United States
Anonymous traveller
The price is NZ$702
includes taxes & fees
1 Nov - 2 Nov
Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

17. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: The spaciousness of the modern house was perfect. We felt right at home. The big pool was highly appreciated. Cons: -"
United States
Anonymous traveller
The price is NZ$1,093
includes taxes & fees
1 Dec - 2 Dec
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

18. Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Cortona
The price is NZ$3,607
includes taxes & fees
1 Nov - 2 Nov
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

19. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is NZ$193
includes taxes & fees
14 Nov - 15 Nov
Vicolo Della Scala Rooms - La Luna
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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Top Cortona Hotel Reviews

Find out more about Cortona

Everything you need to know about Cortona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cortona holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cortona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cortona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cortona holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cortona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cortona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cortona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Cortona?

Yes, there are holiday rentals close to the most popular sights in Cortona, or you can select a more secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theatre during your trip.

What are some of the best holiday rentals that Cortona has to offer?

Beautiful tuscan villa with pool, ideal for groups: This highly rated holiday home rental in Cortona is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cortona?

With 171 Expedia holiday rentals, you're guaranteed to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Cultural attractions include Museum of the Etruscan Academy and Signorelli Theatre, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Villa Bramasole are other places worth a visit.

What’s a holiday rental in Cortona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cortona. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.