Cortona Vacation Rentals from $208: 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

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

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

$142 nightly

Nov 2 - Nov 3

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

$277 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

3. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

$93 nightly

Oct 10 - Oct 11

Total with taxes and fees

4. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

$95 nightly

Oct 13 - Oct 14

Total with taxes and fees

A hotel room with a bed, a chair, a table, and a large window.

5. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

$83 nightly

Oct 15 - Oct 16

Total with taxes and fees

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

6. San Michele al Borgo

Castiglion Fiorentino

Vern

$122 nightly

Oct 10 - Oct 11

Total with taxes and fees

A crowded restaurant with brick walls and multiple tables and chairs.

7. La Locanda di San Francesco

Montepulciano

Colin

$208 nightly

Oct 12 - Oct 13

Total with taxes and fees

An interior courtyard with stone columns, arches, and a mosaic.

8. Meublé Il Riccio

Montepulciano

Christopher

$149 nightly

Oct 22 - Oct 23

Total with taxes and fees

A terrace with a table set for breakfast, overlooking a scenic landscape.

9. Delcorto Suites

Montepulciano

Denise

$188 nightly

Oct 6 - Oct 7

Total with taxes and fees

A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

10. Il Tosco

Montepulciano

Margaret

$234 nightly

Nov 2 - Nov 3

Total with taxes and fees

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

11. Fontelunga Hotel & Villas

Foiano della Chiana

Brian

$276 nightly

Oct 11 - Oct 12

Total with taxes and fees

12. montorio

Montepulciano

Federico

$114 nightly

Oct 5 - Oct 6

Total with taxes and fees

13. iConic Wellness Resort

Arezzo

Rheymarie

$75 nightly

Oct 25 - Oct 26

Total with taxes and fees

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

14. Hotel San Gregorio

Pienza

Nancy

$144 nightly

Oct 28 - Oct 29

Total with taxes and fees

15. Bibi Boutique

Arezzo Centro Storico

$72 nightly

Oct 16 - Oct 17

Total with taxes and fees

A courtyard with a pool, stone benches, and a view of a hill.

16. TH Perugia - Castello di Monterone

Perugia

Sandro

$210 nightly

Oct 30 - Oct 31

Total with taxes and fees

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Monte San Savino

Iain

$243 nightly

Oct 28 - Oct 29

Total with taxes and fees

A modern hotel room with large windows, a bed, a desk, and a chair.

18. B&B 52cento

Arezzo Centro Storico

Tina

$70 nightly

Oct 21 - Oct 22

Total with taxes and fees

A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

19. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

$107 nightly

Nov 1 - Nov 2

Total with taxes and fees

A view of a historic town with prominent buildings and a church tower.

20. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

$83 nightly

Oct 15 - Oct 16

Total with taxes and fees

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Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

10/10 Excellent

"There is nothing to fault here, it’s a perfect hotel. Staff are brilliant, and the buildings and grounds are really well looked after. Breakfast and lunch are ideal too."

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."

Locanda agli Amici

10/10 Excellent

"This was the perfect away from the city stay for us. Cortona was just a quick few day stay for us but the staff/sylvia were fantastic. Room was clean, the breakfast was delicious. A/c and water pressure from the shower was much needed and the location was perfect for us. It is a short walk from downtown Cortona (steep walk into the city and about 15 mins) but the views are unmatched. Sylvia went above and beyond for us picking us up and dropping us off at the bus station. Highly recommend to anyone visiting Cortona."

Hotel San Michele

8/10 Good

"This is a charming hotel housed in a 15th century palazzo as close as you can get to the center of Cortona. The staff was pleasant and helpful. Plus you can pull your car up for luggage drop off - a real convenience in a town center where cars are otherwise restricted. Just note this hotel is in an old building. Not all rooms are serviced by elevator - some stairs required. And like any historic property the facilities have charming quirks - rooms but not all public facilities have A/C, lighting is low and there are no amenities on site other than a lovely buffet breakfast you can enjoy inside or in a garden setting. However its location steps from Cortona’s Piazza Republica, restaurants and shops make up for any shortcomings!"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

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 $208 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. B&B Piccolo Hotel

2. CASA AMBRA

3. Vicolo Della Scala Rooms - La Luna

4. Vicolo Della Scala Rooms - Il Sole

5. Limehome Arezzo Duomo

6. San Michele al Borgo

7. La Locanda di San Francesco

8. Meublé Il Riccio

9. Delcorto Suites

10. Il Tosco

11. Fontelunga Hotel & Villas

12. montorio

13. iConic Wellness Resort

14. Hotel San Gregorio

15. Bibi Boutique

16. TH Perugia - Castello di Monterone

17. Castello di Gargonza

18. B&B 52cento

19. Bed & Breakfast Vicolo dell'Oste

20. Cameracaffè Centro

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

Find out more about Cortona

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