Cortona Vacation Homes from AED 1,002

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. Montecchio di Cortona

Montecchio

Monica S.

AED 413 total

includes taxes & fees

2 Sep - 3 Sep

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

Cortona

AED 346 total

includes taxes & fees

3 Sep - 4 Sep

3. Hillside home in an ancient Camaldolese hamlet

Cortona

AED 1,880 total

includes taxes & fees

19 Sep - 20 Sep

4. Farmhouse with mountain views hot tub

Cortona

AED 1,688 total

includes taxes & fees

2 Sep - 3 Sep

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

Cortona

AED 1,422 total

includes taxes & fees

20 Sep - 21 Sep

6. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

AED 285 total

includes taxes & fees

3 Sep - 4 Sep

7. Dolce Casa 2 by Tiny Away

Rigutino

AED 455 total

includes taxes & fees

3 Sep - 4 Sep

8. Dolce Casa 1 by Tiny Away

Rigutino

AED 481 total

includes taxes & fees

3 Sep - 4 Sep

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

Foiano della Chiana

AED 345 total

includes taxes & fees

2 Sep - 3 Sep

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

Arezzo Centro Storico

Maria Gemma

AED 604 total

includes taxes & fees

1 Oct - 2 Oct

1 bedroom, iron/ironing board, WiFi, bed sheets

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

Toscana

AED 687 total

includes taxes & fees

2 Sep - 3 Sep

12. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

AED 560 total

includes taxes & fees

2 Sep - 3 Sep

13. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

Nigel G.

AED 990 total

includes taxes & fees

2 Oct - 3 Oct

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

Monte San Savino

"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...

Anonymous traveler

AED 904 total

includes taxes & fees

4 Sep - 5 Sep

15. LANDLORD ALBACHIARA

Ramazzano - Le Pulci

Fabio

AED 495 total

includes taxes & fees

7 Sep - 8 Sep

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

Castiglione del Lago

Bin L.

AED 619 total

includes taxes & fees

2 Sep - 3 Sep

17. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

lisciano niccone

AED 1,795 total

includes taxes & fees

14 Sep - 15 Sep

18. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

lisciano niccone

Anonymous traveler

AED 1,975 total

includes taxes & fees

7 Sep - 8 Sep

19. Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi

Lisciano Niccone

Anonymous traveler

AED 1,764 total

includes taxes & fees

1 Oct - 2 Oct

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

Anghiari

AED 384 total

includes taxes & fees

1 Oct - 2 Oct

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

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

10/10 Excellent

"Wir haben unseren Aufenthalt in diesem wunderschönen Haus sehr genossen. Die ruhige Lage und das großzügige Grundstück mit Olivenhain und Swimmingpool waren einfach perfekt zum Entspannen. Das Haus ist sehr gut ausgestattet, insbesondere die Küche, die auch für unsere große Gruppe bestens geeignet war. Wir haben uns rundum wohlgefühlt und würden jederzeit gerne wiederkommen!"

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."

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."

Antico Casale - Holiday Country Villa with swimming pool in Cortona

10/10 Excellent

"Fast and polite communication. Flexible for check in/check out was a big help for us due to traffic issues.The accomodation was exactly what we wanted. The house, the Pool and garden were very clean. The airco and bbq were perfect during the warm weather. Thank you !"

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona vacation homes

1. Montecchio di Cortona

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

3. Hillside home in an ancient Camaldolese hamlet

4. Farmhouse with mountain views hot tub

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. Dolce Casa 1 by Tiny Away

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

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

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

12. Holiday Home 'La Casina All'angolo'

13. Gorgeously restored tranquil farmhouse

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

15. LANDLORD ALBACHIARA

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

17. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

18. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

19. Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi

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

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

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

Monastero di Cortona Hotel & Spa

A small cottage in authentic Tuscany. Serves 4

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort Spa

Relais Villa Baldelli

Villa di Piazzano - Small Luxury Hotel of the World

Hotel San Luca

Antico Casale - Holiday Country Villa with swimming pool in 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. Montecchio di Cortona

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

3. Hillside home in an ancient Camaldolese hamlet

4. Farmhouse with mountain views hot tub

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. Dolce Casa 1 by Tiny Away

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

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

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

12. Holiday Home 'La Casina All'angolo'

13. Gorgeously restored tranquil farmhouse

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

15. LANDLORD ALBACHIARA

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

17. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

18. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

19. Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi

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

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

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