Cortona Vacation Rentals from $223: 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 : Visitors give good reviews to this Cortona vacation home rental, which 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. Another good choice for your trip to Cortona is Casa Bacco - private house with a remarkable garden in the centre of Cortona .

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Our top choices for Cortona vacation rentals

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

$159 nightly

Sep 23 - Sep 24

Total with taxes and fees

2. CASA AMBRA

Cortona Old Town

$140 nightly

Sep 24 - Sep 25

Total with taxes and fees

Apartment (1 Bedroom) | Front of property

3. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

$99 nightly

Sep 16 - Sep 17

Total with taxes and fees

4. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

$101 nightly

Sep 16 - Sep 17

Total with taxes and fees

5. San Michele al Borgo

Castiglion Fiorentino

Vern

$127 nightly

Sep 22 - Sep 23

Total with taxes and fees

6. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

$328 nightly

Sep 19 - Sep 20

Total with taxes and fees

7. iConic Wellness Resort

Arezzo

Rheymarie

$88 nightly

Oct 11 - Oct 12

Total with taxes and fees

8. Castello di Gargonza

Monte San Savino

Ariel

$246 nightly

Sep 22 - Sep 23

Total with taxes and fees

9. La Locanda di San Francesco

Montepulciano

Isabelle

$209 nightly

Sep 27 - Sep 28

Total with taxes and fees

10. Casale dell'Assiolo

Castiglione del Lago

$121 nightly

Sep 13 - Sep 14

Total with taxes and fees

11. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

$83 nightly

Sep 24 - Sep 25

Total with taxes and fees

12. Meublé Il Riccio

Montepulciano

Marlenne

$151 nightly

Oct 8 - Oct 9

Total with taxes and fees

13. Abbadia Sicille Relais

Trequanda

Robert

$141 nightly

Oct 4 - Oct 5

Total with taxes and fees

14. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

$131 nightly

Sep 22 - Sep 23

Total with taxes and fees

Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

15. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

$103 nightly

Oct 7 - Oct 8

Total with taxes and fees

16. Residenza Fabroni

Montepulciano

Nicholas

$85 nightly

Sep 13 - Sep 14

Total with taxes and fees

17. Delcorto Suites

Montepulciano

Denise

$212 nightly

Oct 6 - Oct 7

Total with taxes and fees

18. Affitacamere Maria Gabriella

Pienza

Young Rok

$134 nightly

Oct 4 - Oct 5

Total with taxes and fees

19. Villa Fontis Rapolano

Rapolano Terme

Barbara

$86 nightly

Sep 14 - Sep 15

Total with taxes and fees

20. TH Perugia - Castello di Monterone

Perugia

Baudouin

$205 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Cortona Hotel Reviews

Hotel San Luca

10/10 Excellent

"We stayed in room 62 with a private terrace. The view was something out of a fairy tale. Highly recommend!!!"

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"We had a wonderful time during our holiday at Casina del Bibo! Anna Maria and Lorella gave us a warm welcome, they surprised us with wine, fresh fruits and lots of local products. The appartment was very clean and comfortable, the airconditioning worked perfectly and there were mosquito screens installed in most of the windows. The location of the appartment is ideal. We went to a lot of different cities like Arezzo, Siena, Montepulciano and Perugia during our stay of 14 days. The town of Cortona, which is 15 minutes by car, was very nice to visit for a few times. The appartment is in an a quiet village, but many facilities like a supermarket and restaurants are close by. Our stay at Casina del Bibo surpassed our expectations and we would recommend it to anyone who wants a comfortable quiet place to enjoy their holiday, but who also likes to explore the surrounding towns and countryside."

Cortona Resort - Le Terre Dei Cavalieri

10/10 Excellent

"Beautiful, peaceful resort with helpful staff. Delicious, plentiful breakfast buffet on outside patio included with stay. If A/C is a deal-breaker for you, be aware that it was not very powerful (which is common in Italy, we’ve found) and we thought the room was quite warm and muggy during the summer. However, the staff was very helpful and provided us with a fan that helped a bit. Overall I highly recommend this property."

Relais Villa Baldelli

8/10 Good

"The property was relaxing and quaint. The pool was nice and the overall Tuscan country vibe and decor was nice. The location was good and the rooms were spacious. It was not walkable to anything but if you have a rental car the location is great because Cortana is a wonderful town. The staff is kind and responsive however I had an issue with the cleaning ladies where they disposed of thing of my mine thinking it was trash. I found it odd that cleaning folks would take it upon themselves to touch my things as all. I asked them to not to clean our room anymore and they did it again the next day due to poor internal communication. It was annoying to deal with that but still I would say the staff tried their best to be helpful. Lastly, I was not a fan of their breakfast. They had the basics that were heavily rooted in sweets and pork both of which I don’t eat. They made fresh plain eggs but some veggies and maybe turkey meat would have been nice. Overall, for the price point this place is good."

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 $223 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: Visitors give good reviews to this Cortona vacation home rental, which 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. Another good choice for your trip to Cortona is Casa Bacco - private house with a remarkable garden in the centre of Cortona.

How many vacation rentals are there in Cortona?

With 166 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 Santa Maria Nuova 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. B&B Piccolo Hotel

2. CASA AMBRA

3. Vicolo Della Scala Rooms - La Luna

4. Vicolo Della Scala Rooms - Il Sole

5. San Michele al Borgo

6. Fontelunga Hotel & Villas

7. iConic Wellness Resort

8. Castello di Gargonza

9. La Locanda di San Francesco

10. Casale dell'Assiolo

11. Artisti del Cavallo Tourism

12. Meublé Il Riccio

13. Abbadia Sicille Relais

14. Bed & Breakfast Vicolo dell'Oste

15. DormiVeglia B&B

16. Residenza Fabroni

17. Delcorto Suites

18. Affitacamere Maria Gabriella

19. Villa Fontis Rapolano

20. TH Perugia - Castello di Monterone

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Hotel San Luca

Find out more about Cortona

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