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

Cortona Vacation Rentals

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Our top choices for Cortona vacation 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 CA $199
CA $222 total
includes taxes & fees
Nov 2 - Nov 3
B&B Piccolo Hotel

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is CA $304
CA $337 total
includes taxes & fees
Nov 6 - Nov 7
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 CA $146
CA $153 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $193
CA $226 total
includes taxes & fees
Nov 4 - Nov 5
Cortona Shabby Chic House<br>(Independent & Balcony)

5. Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
The price is CA $183
CA $191 total
includes taxes & fees
Nov 1 - Nov 2
Casa Beppina Cortona by Interhome

6. 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
The price is CA $130
CA $164 total
includes taxes & fees
Nov 1 - Nov 2
Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome

7. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is CA $134
CA $151 total
includes taxes & fees
Nov 4 - Nov 5
Vicolo Della Scala Rooms - La Luna

8. 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 CA $210
CA $246 total
includes taxes & fees
Nov 10 - Nov 11
Cortonas Rooftop Nest

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 CA $99
CA $127 total
includes taxes & fees
Oct 28 - Oct 29
Vacation home with a panoramic terrace, ideal for families and couples

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

Cosy apartment for 2 people with WIFI, TV and pets allowed
Cortona Old Town
The price is CA $182
CA $235 total
includes taxes & fees
Nov 3 - Nov 4
Cosy apartment for 2 people with WIFI, TV and pets allowed

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 CA $124
CA $152 total
includes taxes & fees
Nov 3 - Nov 4
Montecchio di Cortona

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 traveller
The price is CA $309
CA $375 total
includes taxes & fees
Nov 3 - Nov 4
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

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 CA $180
CA $187 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $512
CA $577 total
includes taxes & fees
Nov 3 - Nov 4
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

15. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is CA $8,500
CA $8,500 total
includes taxes & fees
Oct 30 - Oct 31
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

16. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
The price is CA $319
CA $327 total
includes taxes & fees
Oct 29 - Oct 30
Wohnung la Mimosa by Interhome

17. 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 CA $516
CA $581 total
includes taxes & fees
Nov 1 - Nov 2
Apartment 'Magazzino 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

18. 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 CA $756
CA $821 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

19. 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 CA $2,819
CA $2,850 total
includes taxes & fees
Nov 3 - Nov 4
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

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

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
The price is CA $164
CA $170 total
includes taxes & fees
Oct 29 - Oct 30
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cortona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.