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

Cortona Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Cortona vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. 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 AED 522
AED 582 total
includes taxes & fees
2 Nov - 3 Nov
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is AED 783
AED 868 total
includes taxes & fees
5 Nov - 6 Nov
CASA AMBRA
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

3. 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 AED 385
AED 402 total
includes taxes & fees
9 Nov - 10 Nov
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
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 AED 353
AED 396 total
includes taxes & fees
14 Nov - 15 Nov
Vicolo Della Scala Rooms - La Luna
A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

5. 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 AED 381
AED 470 total
includes taxes & fees
28 Oct - 29 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.

6. Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
The price is AED 482
AED 502 total
includes taxes & fees
18 Oct - 19 Oct
Casa Beppina Cortona by Interhome
A staircase with two lit lanterns on the wall.

7. 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 AED 509
AED 595 total
includes taxes & fees
18 Oct - 19 Oct
Cortona Shabby Chic House<br>(Independent & Balcony)
A black dog with a blue collar sitting on stone steps in front of a brown double door with a metal arch above it.

8. Nice apartment for 2 people with WIFI, TV and pets allowed

Nice apartment for 2 people with WIFI, TV and pets allowed
Cortona Old Town
The price is AED 478
AED 618 total
includes taxes & fees
28 Oct - 29 Oct
Nice apartment for 2 people with WIFI, TV and pets allowed
A park with picnic tables, a playground, and a gravel path.

9. 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 AED 259
AED 334 total
includes taxes & fees
17 Oct - 18 Oct
Vacation home with a panoramic terrace, ideal for families and couples
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

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 AED 614
AED 717 total
includes taxes & fees
6 Nov - 7 Nov
Cortonas Rooftop Nest
Dining

11. 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 AED 325
AED 400 total
includes taxes & fees
19 Oct - 20 Oct
Montecchio di Cortona
A stone building with a patio area featuring outdoor furniture and potted plants.

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

Podere Casorbica with free parking, large garden, private pool.
cortona
9.6 out of 10, Exceptional, (18 reviews)
"Giorgio is very welcoming, the house has a very authentic feel. "
Netherlands
Joost B.
The price is AED 630
AED 737 total
includes taxes & fees
17 Oct - 18 Oct
Podere Casorbica with free parking, large garden, private pool.
A building with a stone facade, multiple windows, and a balcony.

13. 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 traveler
The price is AED 814
AED 985 total
includes taxes & fees
18 Oct - 19 Oct
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A garden patio with a stone building, outdoor seating, and a view of a hill.

14. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is AED 22,276
AED 22,276 total
includes taxes & fees
28 Oct - 29 Oct
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
A building with a stone facade, multiple windows, and a balcony.

15. 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 AED 1,374
AED 1,546 total
includes taxes & fees
18 Oct - 19 Oct
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and potted plants.

16. B&B Casa Fattorini Apartment Bernie

B&B Casa Fattorini Apartment Bernie
Toscana
The price is AED 741
AED 869 total
includes taxes & fees
28 Oct - 29 Oct
B&B Casa Fattorini Apartment Bernie
A stone building with a balcony, an archway, and potted plants.

17. 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 AED 527
AED 544 total
includes taxes & fees
2 Nov - 3 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A living room with a brick fireplace, a sofa, a patterned armchair, and a shelf with various items.

18. B&B Casa Fattorini Apartment Ada

B&B Casa Fattorini Apartment Ada
Toscana
The price is AED 824
AED 943 total
includes taxes & fees
28 Oct - 29 Oct
B&B Casa Fattorini Apartment Ada
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

19. 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 traveler
The price is AED 1,356
AED 1,527 total
includes taxes & fees
18 Oct - 19 Oct
Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
Exterior

20. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
Wohnung la Mimosa by Interhome
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

Relais Villa Baldelli

Relais Villa Baldelli

10/10 Excellent
"Beautiful property and amazing service!"
Michael 7-night trip
Posted 1 day ago
Relais Villa Baldelli

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a 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 theater during your trip.

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

Beautiful tuscan villa with pool, ideal for groups: This highly rated vacation home rental in Cortona is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Cortona?

With 171 Expedia vacation rentals, you're sure 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 vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.