Cortona Vacation Homes from AED 1,034

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

26 Aug - 27 Aug

2. Montecchio di Cortona

Montecchio

Monica S.

AED 416 total

includes taxes & fees

24 Aug - 25 Aug

3. Farmhouse with mountain views hot tub

Cortona

AED 1,702 total

includes taxes & fees

24 Aug - 25 Aug

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

Cortona

AED 1,308 total

includes taxes & fees

26 Aug - 27 Aug

5. Hillside home in an ancient Camaldolese hamlet

Cortona

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

sansepolcro (arezzo)

Margit H.

AED 661 total

includes taxes & fees

30 Aug - 31 Aug

7. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

AED 1,120 total

includes taxes & fees

15 Sep - 16 Sep

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

Anghiari

AED 429 total

includes taxes & fees

17 Sep - 18 Sep

View all properties

Find vacation rentals that suit your style

Villas

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Cortona Hotel Reviews

Hotel San Michele

10/10 Excellent

"Reception staff were extremely helpful when we were unloading and loading a great deal of wedding paraphernalia from the car before it went into the public carpark."

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!"

Room 1

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

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

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

Relais Villa Baldelli

A small cottage in authentic Tuscany. Serves 4

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

Hotel San Michele