Cortona Vacation Rentals : Search Short-Term Rentals

Q: 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.

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Our top choices for Cortona vacation 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

Cortona Old Town

Joseph

$104 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

Cortona Old Town

$206 nightly

Nov 12 - Nov 13

Total with taxes and fees

A view from a window overlooking a courtyard with stone buildings and a tower.

3. La Finestra sul Teatro

Cortona Old Town

Jean V. A.

$207 nightly

Dec 8 - Dec 9

Total with taxes and fees

A staircase with two lit lanterns on the wall.

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

Cortona Old Town

Erin

$150 nightly

Nov 12 - Nov 13

Total with taxes and fees

A black dog with a blue collar sitting in front of a brown double door with a stone archway.

5. Casa Beppina Cortona by Interhome

Cortona Old Town

$136 nightly

Nov 14 - Nov 15

Total with taxes and fees

A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

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

Cortona Old Town

$105 nightly

Nov 12 - Nov 13

Total with taxes and fees

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

7. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

$99 nightly

Nov 16 - Nov 17

Total with taxes and fees

A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

8. Cortonas Rooftop Nest

Cortona Old Town

Robin F.

$173 nightly

Nov 27 - Nov 28

Total with taxes and fees

A park with picnic tables, a playground, and a gravel path.

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

Cortona

$83 nightly

Nov 12 - Nov 13

Total with taxes and fees

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 people with WIFI, TV and pets allowed

Cortona Old Town

$170 nightly

Nov 14 - Nov 15

Total with taxes and fees

11. Montecchio di Cortona

Montecchio

Monica S.

$101 nightly

Nov 12 - Nov 13

Total with taxes and fees

A building with a stone facade, multiple windows, and a balcony.

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

Cortona

Anonymous traveler

$286 nightly

Nov 30 - Dec 1

Total with taxes and fees

A stone building with a balcony, an archway, and potted plants.

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

Cortona

Bonnie B.

$129 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Cortona

$446 nightly

Dec 8 - Dec 9

Total with taxes and fees

A garden patio with a stone building, outdoor seating, and a view of a hill.

15. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

Cortona

$6,985 nightly

Nov 14 - Nov 15

Total with taxes and fees

16. Wohnung la Mimosa by Interhome

Cortona

$236 nightly

Nov 14 - Nov 15

Total with taxes and fees

A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

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

Cortona

"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...

Anonymous traveler

$462 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Cortona

Anonymous traveler

$595 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone wall, a round table with chairs, a bowl of fruit, and a glass of juice.

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

Cortona

$1,615 nightly

Dec 5 - Dec 6

Total with taxes and fees

20. Nice apartment for 2 people with WIFI, A/C and pets allowed

Cortona Old Town

$109 nightly

Nov 16 - Nov 17

Total with taxes and fees

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Top Cortona Hotel Reviews

Villa Santa Margherita

10/10 Excellent

"Recommend do not arrive late at night into Cortona upon arrival. The roads are narrow and NOT like USA at all. GPS showed fastest route. However, part of the road are extremely narrow and hilly. There are no street signs at all. Local people are extremely helpful and friendly. We got lost and they showed us to the hotel."

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"The host was very nice and met us at the property. She gave us a tour of the apartment and explained everything for us. She also provided some good snacks made by her mother and a bottle of wine. The location is perfect for visiting Cortana and many other small towns in the area. We had a wonderful time during our stay."

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.

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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.

Cortona Vacation Rentals

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Check prices for these dates

Our top choices for Cortona vacation rentals

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

2. CASA AMBRA

3. La Finestra sul Teatro

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

5. Casa Beppina Cortona by Interhome

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

7. Vicolo Della Scala Rooms - La Luna

8. Cortonas Rooftop Nest

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

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

11. Montecchio di Cortona

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

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

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

15. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

16. Wohnung la Mimosa by Interhome

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

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

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

20. Nice apartment for 2 people with WIFI, A/C and pets allowed

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Villa Santa Margherita

Find out more about Cortona

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