Cortona Vacation Rentals from ₩116,176: Search Short-Term Rentals

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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

₩240,337 total

includes taxes & fees

Sep 23 - Sep 24

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

₩215,112 total

includes taxes & fees

Sep 18 - Sep 19

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

₩159,341 total

includes taxes & fees

Sep 14 - Sep 15

4. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

₩177,285 total

includes taxes & fees

Sep 23 - Sep 24

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

5. San Michele al Borgo

Castiglion Fiorentino

Vern

₩221,353 total

includes taxes & fees

Sep 19 - Sep 20

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

6. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

₩490,575 total

includes taxes & fees

Sep 19 - Sep 20

7. iConic Wellness Resort

Arezzo

Rheymarie

₩138,480 total

includes taxes & fees

Oct 11 - Oct 12

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

8. Castello di Gargonza

Monte San Savino

Ariel

₩376,457 total

includes taxes & fees

Sep 17 - Sep 18

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

9. La Locanda di San Francesco

Montepulciano

Isabelle

₩349,308 total

includes taxes & fees

Oct 8 - Oct 9

10. Casale dell'Assiolo

Castiglione del Lago

₩195,637 total

includes taxes & fees

Sep 13 - Sep 14

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

11. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

₩130,629 total

includes taxes & fees

Sep 18 - Sep 19

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

12. Meublé Il Riccio

Montepulciano

Marlenne

₩250,674 total

includes taxes & fees

Sep 15 - Sep 16

A historic building with a tower, a courtyard, and a well-lit entrance.

13. Abbadia Sicille Relais

Trequanda

Robert

₩210,548 total

includes taxes & fees

Oct 6 - Oct 7

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

14. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

₩207,906 total

includes taxes & fees

Sep 11 - Sep 12

A spa area with a stone-walled arch, a hot tub, and a small window.

15. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

₩175,056 total

includes taxes & fees

Oct 4 - Oct 5

An arched doorway leading to a building with a wooden door and a staircase.

16. Residenza Fabroni

Montepulciano

Nicholas

₩131,625 total

includes taxes & fees

Sep 13 - Sep 14

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

17. Delcorto Suites

Montepulciano

Denise

₩325,808 total

includes taxes & fees

Oct 6 - Oct 7

A patio area with outdoor seating, potted plants, and a view of the landscape.

18. Affitacamere Maria Gabriella

Pienza

Young Rok

₩205,141 total

includes taxes & fees

Oct 4 - Oct 5

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

19. Villa Fontis Rapolano

Rapolano Terme

Barbara

₩140,918 total

includes taxes & fees

Sep 14 - Sep 15

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

20. TH Perugia - Castello di Monterone

Perugia

Baudouin

₩322,367 total

includes taxes & fees

Sep 18 - Sep 19

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Top Cortona Hotel Reviews

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

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."

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."

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.

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.

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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

Il Falconiere - Relais e Chateaux

Hotel San Luca

Monastero di Cortona Hotel & Spa

Villa Borgo San Pietro

Villa di Piazzano - Small Luxury Hotel of the World

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort Spa

Relais Villa Baldelli

Locanda agli Amici

Find out more about Cortona

Frequently asked questions

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