Cortona Vacation Homes from AED 287

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

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Our top choices for Cortona vacation homes

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

Cortona

AED 347 total

includes taxes & fees

25 Sep - 26 Sep

2. Montecchio di Cortona

Montecchio

Monica S.

AED 415 total

includes taxes & fees

21 Sep - 22 Sep

3. Farmhouse with mountain views hot tub

Cortona

AED 1,698 total

includes taxes & fees

29 Aug - 30 Aug

4. Hillside home in an ancient Camaldolese hamlet

Cortona

AED 1,891 total

includes taxes & fees

26 Sep - 27 Sep

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

Cortona

AED 1,308 total

includes taxes & fees

30 Aug - 31 Aug

6. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

AED 287 total

includes taxes & fees

1 Sep - 2 Sep

7. Dolce Casa 2 by Tiny Away

Rigutino

AED 458 total

includes taxes & fees

3 Sep - 4 Sep

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

Foiano della Chiana

AED 347 total

includes taxes & fees

1 Sep - 2 Sep

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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."

"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."

Room 1

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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. Hillside home in an ancient Camaldolese hamlet

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

6. Happy Nest Tuscany Between Florence and Rome

7. Dolce Casa 2 by Tiny Away

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

9. Dolce Casa 1 by Tiny Away

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

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

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

13. Holiday Home 'La Casina All'angolo'

14. Gorgeously restored tranquil farmhouse

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

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

17. Casale I Tre Cipressi

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

19. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

20. Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

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

Locanda agli Amici

Hotel San Luca

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

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. Hillside home in an ancient Camaldolese hamlet

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

6. Happy Nest Tuscany Between Florence and Rome

7. Dolce Casa 2 by Tiny Away

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

9. Dolce Casa 1 by Tiny Away

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

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

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

13. Holiday Home 'La Casina All'angolo'

14. Gorgeously restored tranquil farmhouse

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

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

17. Casale I Tre Cipressi

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

19. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

20. Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

A small cottage in authentic Tuscany. Serves 4