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

Cortona Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cortona holiday rentals

A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

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

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
The price is HK$835
HK$871 total
includes taxes & fees
24 Oct - 25 Oct
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

2. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is HK$1,219
HK$1,376 total
includes taxes & fees
21 Oct - 22 Oct
B&B Piccolo Hotel
A view from a window overlooking a courtyard with stone buildings and a tower.

3. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is HK$1,045
HK$1,634 total
includes taxes & fees
4 Oct - 5 Oct
La Finestra sul Teatro
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is HK$797
HK$912 total
includes taxes & fees
5 Oct - 6 Oct
Vicolo Della Scala Rooms - La Luna
A park with picnic tables, a playground, and a gravel path.

5. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is HK$563
HK$723 total
includes taxes & fees
27 Sept - 28 Sept
Holiday home with panoramic terrace ideal for families and couples
A staircase with two lit lanterns on the wall.

6. 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
Cortona Shabby Chic House<br>(Independent & balcony)
A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

7. Vacation home Beppina, typical cortonese house, in the center, animals welcome

Vacation home Beppina, typical cortonese house, in the center, animals welcome
Cortona Old Town
The price is HK$827
HK$1,019 total
includes taxes & fees
25 Oct - 26 Oct
Vacation home Beppina, typical cortonese house, in the center, animals welcome
A black dog with a blue collar sitting in front of a brown double door with a stone archway.

8. Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
The price is HK$1,045
HK$1,089 total
includes taxes & fees
25 Oct - 26 Oct
Casa Beppina Cortona by Interhome
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

9. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is HK$2,557
HK$2,839 total
includes taxes & fees
8 Oct - 9 Oct
CASA AMBRA
A black dog with a blue collar sitting on stone steps in front of a brown double door with a metal arch above it.

10. Beautiful apartment for 2 guests with WIFI, TV and pets allowed

Beautiful apartment for 2 guests with WIFI, TV and pets allowed
Cortona Old Town
The price is HK$1,036
HK$1,205 total
includes taxes & fees
25 Oct - 26 Oct
Beautiful apartment for 2 guests with WIFI, TV and pets allowed
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

11. 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 HK$1,446
HK$1,680 total
includes taxes & fees
28 Sept - 29 Sept
Cortonas Rooftop Nest
A swimming pool with stone edges, surrounded by greenery and a view of a hill with a castle-like structure in the background.

12. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Cortona (AR)
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Die Anlage strahlt einen wunderbaren nostalgischen Charme aus. Elisa hat sich hervorragend um uns gekümmert. Per Whatsapp wurden sämtliche Fragen in Kürze geklärt. Cons: Die Terrasse ist kaum zu nützen, da vor allem am Abend die Mückenplage unangenehm ist. Die Fenster und Türen der Wohnung haben alle Fliegen- und Mückengitter."
Germany
Anonymous traveller
The price is HK$1,774
HK$5,095 total
includes taxes & fees
25 Sept - 26 Sept
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

13. 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 HK$709
HK$871 total
includes taxes & fees
19 Oct - 20 Oct
Montecchio di Cortona
An outdoor patio with a table and chairs, surrounded by greenery and potted plants.

14. B&B Casa Fattorini Apartment Bernie

B&B Casa Fattorini Apartment Bernie
Toscana
The price is HK$1,616
HK$1,894 total
includes taxes & fees
7 Oct - 8 Oct
B&B Casa Fattorini Apartment Bernie
A living room with a brick fireplace, a sofa, a patterned armchair, and a shelf with various items.

15. B&B Casa Fattorini Apartment Ada

B&B Casa Fattorini Apartment Ada
Toscana
The price is HK$1,796
HK$2,056 total
includes taxes & fees
7 Oct - 8 Oct
B&B Casa Fattorini Apartment Ada
A garden patio with a stone building, outdoor seating, and a view of a hill.

16. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is HK$48,735
HK$48,735 total
includes taxes & fees
30 Sept - 1 Oct
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

17. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
The price is HK$1,821
HK$1,866 total
includes taxes & fees
26 Sept - 27 Sept
Wohnung la Mimosa by Interhome
A building with a stone facade, multiple windows, and a balcony.

18. 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 HK$2,299
HK$2,673 total
includes taxes & fees
4 Oct - 5 Oct
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A hot tub in a grassy outdoor area with a mountain view.

19. Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
The price is HK$1,912
HK$3,545 total
includes taxes & fees
27 Sept - 28 Sept
Farmhouse with mountain views hot tub
A narrow alleyway with brick buildings, potted plants, and a tree with pink flowers.

20. B&B Fattorini House

B&B Fattorini House
Toscana
The price is HK$3,142
HK$3,618 total
includes taxes & fees
7 Oct - 8 Oct
B&B Fattorini House
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Service was top notch and Claudio at the bar made the best cocktails"
Alexander 2-night trip
Posted 2 days ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday apartments in Cortona using one of the methods below:

  • View our selection of featured holiday rentals in Cortona
  • Use the map to find apartments and other holiday homes in the Cortona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cortona while they last

Look no further and take a look at our great range of rental properties in Cortona!

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. Another good choice for your trip to Cortona is Casa Bacco - private house with a remarkable garden in the centre of Cortona.

How many holiday rentals are there in Cortona?

With 168 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.