Cortona Vacation Rentals : Search Short-Term Rentals

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Our top choices for Cortona vacation rentals

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

￥26,333 total

includes taxes & fees

Aug 16 - Aug 17

Apartment (1 Bedroom) | Front of property

2. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

￥18,413 total

includes taxes & fees

Aug 22 - Aug 23

3. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

￥20,492 total

includes taxes & fees

Aug 17 - Aug 18

4. Meublé Il Riccio

Montepulciano

Marlenne

￥28,958 total

includes taxes & fees

Aug 14 - Aug 15

5. La Locanda di San Francesco

Montepulciano

Isabelle

￥23,679 total

includes taxes & fees

Aug 25 - Aug 26

6. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

￥16,288 total

includes taxes & fees

Aug 24 - Aug 25

Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

7. iConic Wellness Resort

Arezzo

Rheymarie

￥23,758 total

includes taxes & fees

Sep 10 - Sep 11

8. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

￥23,554 total

includes taxes & fees

Aug 14 - Aug 15

9. Abbadia Sicille Relais

Trequanda

Robert

￥33,812 total

includes taxes & fees

Aug 23 - Aug 24

10. Delcorto Suites

Montepulciano

Melissa Hyun Joo

￥34,964 total

includes taxes & fees

Aug 18 - Aug 19

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

11. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

￥23,027 total

includes taxes & fees

Aug 16 - Aug 17

12. Il Tosco

Montepulciano

Margaret

￥48,770 total

includes taxes & fees

Aug 14 - Aug 15

13. Hotel San Gregorio

Pienza

Nancy

￥42,383 total

includes taxes & fees

Aug 25 - Aug 26

14. TH Perugia - Castello di Monterone

Perugia

Larraine

￥35,816 total

includes taxes & fees

Aug 23 - Aug 24

15. La Piccola Locanda

Chiusi

Jeffery

￥21,837 total

includes taxes & fees

Aug 14 - Aug 15

Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

16. B&B 52cento

Arezzo Centro Storico

Tina

￥15,437 total

includes taxes & fees

Sep 2 - Sep 3

17. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

￥42,971 total

includes taxes & fees

Aug 18 - Aug 19

18. San Michele al Borgo

Castiglion Fiorentino

Vern

￥25,583 total

includes taxes & fees

Sep 12 - Sep 13

19. Residenza Fabroni

Montepulciano

Nicholas

￥15,855 total

includes taxes & fees

Aug 20 - Aug 21

20. Casale dell'Assiolo

Castiglione del Lago

￥20,529 total

includes taxes & fees

Sep 7 - Sep 8

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Top Cortona Hotel Reviews

Locanda agli Amici

10/10 Excellent

"Staying here was amazing. We were in the heart of Cortona, which was so peaceful compared to busier areas of Italy. Very authentic. Sylvia made the entire stay wonderful. The hospitality here is unmatched. The food is delicious. The rooms are cute and the view...the view is stunning. I am so happy we decided to stay here!! I would 10/10 recommend. Taxis were hard to find, but Silvia drove us whenever we couldn't find a taxi. She is so friendly and welcoming. On top of that, we had a lovely breakfast buffet every morning. I enjoyed sitting outside looking at the view while eating. Their cappuccinos were fantastic, and the table is already set up before you arrive. Dinner is the same way. It's the little touches like that that made the stay top tier. They pay attention, get to know their guests, and genuinely love what they do. Also, the food was AMAZING. I love that they have their own bistro there and that we didn't have to plan where to go eat a couple of nights during our visit. It was easily my favorite restaurant in Italy. I cannot compliment Locanda Agli Amici enough, but especially Sylvia, who made the stay so warm and welcoming. I hope we get to visit again."

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

10/10 Excellent

"Lovely villa in great location. Bedrooms were all good size, good kitchen and indoor/outdoor eating areas. Excellent air conditioning. Beautiful grounds with olive trees and lovely pool area. Beautiful view of Cortona."

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"We absolutely loved our stay at Anna Maria's property in Fratticciola. The bedrooms are roomy, warmly decorated. We had fun cooking in the galley kitchen--the cooktop range was easy to operate and included a small burner just for the mocha. We didn't use the oven, but one is available. There are plenty of plates, bowls, silverware along with a few cooking supplies including their own delicious olive oil. Our stay was also greeted with some delicious homemade Cantucci and vin santo, a plate of bruschetta, and Panzanella. The futon in the living/dining area is just enough comfort but does seat low to the ground. The cottage has a wonderful homey feeling and is slightly tucked away from the road with small inviting gardens for lounging, reading, or sipping espresso. There is also a table and chairs for outdoor dining below the stairs. If you do not want to sit in the garden, a small table with two chairs are folded at the top of the stairs on the platform. Casa di Bini is a rustic, charming place with its own sense of home and romance. The surrounding area is gorgeous, quiet, and you are short drives from many beautiful places. Highly recommended!"

Cortona Resort Spa

10/10 Excellent

"Pro: gorgeous and spacious property, we were upgraded to a junior suite that was lovely, attentive staff, and incredible amenities. Pool was wonderful for tired bodies. Con: very few. The restaurant on site has pretty limited menu, toilet in room kept running all night long- informed staff on checkout (as it was troublesome to flush, and wasting water), fridge in room- housed in a cabinet that I feel caused it to overheat… and therefore was not very powerful enough to keep drinks cold. Loved this place and the attentive staff. Super friendly and wonderful hospitality."

Find out more about Cortona

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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?

Podere Casorbica with free parking, large garden, private pool.: Visitors give good reviews to this Cortona vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a balcony and a garden. Another good choice for your trip to Cortona is beautiful tuscan villa with pool, ideal for groups.

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 Signorelli Theatre and Museum of the Etruscan Academy, 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.

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Check prices for these dates

Our top choices for Cortona vacation rentals

1. B&B Piccolo Hotel

2. Vicolo Della Scala Rooms - La Luna

3. Vicolo Della Scala Rooms - Il Sole

4. Meublé Il Riccio

5. La Locanda di San Francesco

6. Cameracaffè Centro

7. iConic Wellness Resort

8. Bed & Breakfast Vicolo dell'Oste

9. Abbadia Sicille Relais

10. Delcorto Suites

11. DormiVeglia B&B

12. Il Tosco

13. Hotel San Gregorio

14. TH Perugia - Castello di Monterone

15. La Piccola Locanda

16. B&B 52cento

17. Fontelunga Hotel & Villas

18. San Michele al Borgo

19. Residenza Fabroni

20. Casale dell'Assiolo

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Locanda agli Amici

Monastero di Cortona Hotel & Spa

Hotel San Luca

Hotel San Michele

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

Relais Villa Baldelli

A small cottage in authentic Tuscany. Serves 4

Cortona Resort Spa

Villa Santa Margherita

Find out more about Cortona

Frequently asked questions

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