Cortona Vacation Homes from ￥12,433

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

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Our top choices for Cortona vacation homes

A park with picnic tables, a playground, and a gravel path.

1. Holiday home with panoramic terrace ideal for families and couples

Cortona

￥15,057 total

includes taxes & fees

Aug 27 - Aug 28

2. Montecchio di Cortona

Montecchio

Monica S.

￥18,000 total

includes taxes & fees

Aug 31 - Sep 1

A hot tub in a grassy outdoor area with a mountain view.

3. Farmhouse with mountain views hot tub

Cortona

￥73,619 total

includes taxes & fees

Aug 27 - Aug 28

A building with a stone facade, multiple windows, and a balcony.

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Cortona

￥62,033 total

includes taxes & fees

Sep 22 - Sep 23

5. Hillside home in an ancient Camaldolese hamlet

Cortona

A stone building with a pool, surrounded by trees and outdoor seating.

6. -2 / 3-seater garage with private garden, swimming pool, park and spa

sansepolcro (arezzo)

Margit H.

￥28,578 total

includes taxes & fees

Aug 30 - Aug 31

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

7. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

￥48,620 total

includes taxes & fees

Sep 15 - Sep 16

8. Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi

Anghiari

￥18,557 total

includes taxes & fees

Aug 27 - Aug 28

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Top Cortona Hotel Reviews

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."

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

Cortona Vacation Homes information

Number of reviews	20
Accommodation	221 Vacation Homes
Lowest Price	￥12,433
Highest Price	￥652,133

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Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

2. Montecchio di Cortona

3. Farmhouse with mountain views hot tub

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

5. Hillside home in an ancient Camaldolese hamlet

6. -2 / 3-seater garage with private garden, swimming pool, park and spa

7. Suite Gioconda - Podere Casa Rossa in Pienza

8. Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi

9. Happy Nest Tuscany Between Florence and Rome

10. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

11. Dolce Casa 2 by Tiny Away

12. Dolce Casa 1 by Tiny Away

13. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

14. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

15. Double room with private bathroom in the countryside 5 minutes from Montepulciano

16. Gorgeously restored tranquil farmhouse

17. Holiday Home 'La Casina All'angolo'

18. Welcome to Villa Dolce Vita - your private paradise in Tuscany

19. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

20. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

A small cottage in authentic Tuscany. Serves 4

Cortona Resort Spa

Relais Villa Baldelli

Hotel San Michele

Monastero di Cortona Hotel & Spa

Villa di Piazzano - Small Luxury Hotel of the World

Il Falconiere - Relais e Chateaux

Locanda agli Amici

Hotel San Luca

Find out more about Cortona

Cortona Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Cortona

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

2. Montecchio di Cortona

3. Farmhouse with mountain views hot tub

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

5. Hillside home in an ancient Camaldolese hamlet

6. -2 / 3-seater garage with private garden, swimming pool, park and spa

7. Suite Gioconda - Podere Casa Rossa in Pienza

8. Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi

9. Happy Nest Tuscany Between Florence and Rome

10. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

11. Dolce Casa 2 by Tiny Away

12. Dolce Casa 1 by Tiny Away

13. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

14. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

15. Double room with private bathroom in the countryside 5 minutes from Montepulciano

16. Gorgeously restored tranquil farmhouse

17. Holiday Home 'La Casina All'angolo'

18. Welcome to Villa Dolce Vita - your private paradise in Tuscany

19. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

20. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

A small cottage in authentic Tuscany. Serves 4

Find out more about Cortona

Cortona Vacation Homes information

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