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

Cortona Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$140 nightly
The price is $158
Oct 27 - Oct 28
Total with taxes and fees
B&B Piccolo Hotel
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

2. 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.
$105 nightly
The price is $109
Nov 3 - Nov 4
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
$198 nightly
The price is $219
Nov 19 - Nov 20
Total with taxes and fees
CASA AMBRA
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
$95 nightly
The price is $109
Oct 23 - Oct 24
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A staircase with two lit lanterns on the wall.

5. 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
$159 nightly
The price is $162
Oct 27 - Oct 28
Total with taxes and fees
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.

6. 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
$114 nightly
The price is $118
Oct 21 - Oct 22
Total with taxes and fees
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.

7. Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
$131 nightly
The price is $137
Oct 27 - Oct 28
Total with taxes and fees
Casa Beppina Cortona by Interhome
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. Cosy apartment for 2 guests with WIFI, TV and pets allowed

Cosy apartment for 2 guests with WIFI, TV and pets allowed
Cortona Old Town
$163 nightly
The price is $168
Oct 27 - Oct 28
Total with taxes and fees
Cosy apartment for 2 guests 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
$99 nightly
The price is $99
Oct 27 - Oct 28
Total with taxes and fees
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.
$192 nightly
The price is $196
Nov 6 - Nov 7
Total with taxes and fees
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.
$109 nightly
The price is $109
Nov 3 - Nov 4
Total with taxes and fees
Montecchio di Cortona
A building with a stone facade, multiple windows, and a balcony.

12. 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
$263 nightly
The price is $268
Oct 27 - Oct 28
Total with taxes and fees
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.

13. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
$6,086 nightly
The price is $6,086
Oct 27 - Oct 28
Total with taxes and fees
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
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
$231 nightly
The price is $237
Oct 27 - Oct 28
Total with taxes and fees
B&B Casa Fattorini Apartment Bernie
A stone building with a balcony, an archway, and potted plants.

15. 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.
$144 nightly
The price is $148
Nov 3 - Nov 4
Total with taxes and fees
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A building with a stone facade, multiple windows, and a balcony.

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

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
$415 nightly
The price is $421
Oct 27 - Oct 28
Total with taxes and fees
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A living room with a brick fireplace, a sofa, a patterned armchair, and a shelf with various items.

17. B&B Casa Fattorini Apartment Ada

B&B Casa Fattorini Apartment Ada
Toscana
$257 nightly
The price is $257
Oct 27 - Oct 28
Total with taxes and fees
B&B Casa Fattorini Apartment Ada
Exterior

18. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
$229 nightly
The price is $234
Oct 27 - Oct 28
Total with taxes and fees
Wohnung la Mimosa by Interhome
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
$410 nightly
The price is $416
Oct 27 - Oct 28
Total with taxes and fees
Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

20. 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 traveler
$643 nightly
The price is $648
Nov 3 - Nov 4
Total with taxes and fees
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Awesome spot to stay, staff treats you like royalty. Nice little spot to stay for a few days after one of the bigger cities in Italy!"
Shayne 2-night trip
Posted 6 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Everything you need to know about Cortona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortona vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cortona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.