Cortona Vacation Homes from AED 1,000

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

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Our top choices for Cortona vacation homes

1. Montecchio di Cortona

Montecchio

Monica S.

AED 413 total

includes taxes & fees

7 Sep - 8 Sep

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

Cortona

AED 375 total

includes taxes & fees

20 Sep - 21 Sep

3. Hillside home in an ancient Camaldolese hamlet

Cortona

AED 1,448 total

includes taxes & fees

3 Oct - 4 Oct

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

Cortona

5. Farmhouse with mountain views hot tub

Cortona

AED 1,689 total

includes taxes & fees

11 Sep - 12 Sep

6. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

AED 285 total

includes taxes & fees

4 Sep - 5 Sep

7. Dolce Casa 2 by Tiny Away

Rigutino

AED 456 total

includes taxes & fees

6 Sep - 7 Sep

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

Foiano della Chiana

AED 344 total

includes taxes & fees

4 Sep - 5 Sep

9. Dolce Casa 1 by Tiny Away

Rigutino

AED 480 total

includes taxes & fees

6 Sep - 7 Sep

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

Arezzo Centro Storico

Maria Gemma

AED 602 total

includes taxes & fees

4 Oct - 5 Oct

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

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

Toscana

AED 690 total

includes taxes & fees

30 Sep - 1 Oct

12. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

Nigel G.

AED 976 total

includes taxes & fees

4 Oct - 5 Oct

13. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

AED 560 total

includes taxes & fees

3 Oct - 4 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 905 total

includes taxes & fees

4 Sep - 5 Sep

15. LANDLORD ALBACHIARA

Ramazzano - Le Pulci

Fabio

AED 484 total

includes taxes & fees

14 Sep - 15 Sep

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

Castiglione del Lago

Bin L.

AED 617 total

includes taxes & fees

10 Sep - 11 Sep

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

lisciano niccone

AED 1,796 total

includes taxes & fees

4 Sep - 5 Sep

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

Lisciano Niccone

Anonymous traveler

AED 1,761 total

includes taxes & fees

2 Oct - 3 Oct

Coffee/tea maker, fridge, microwave, stovetop

19. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

AED 519 total

includes taxes & fees

14 Sep - 15 Sep

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

lisciano niccone

Anonymous traveler

AED 1,971 total

includes taxes & fees

7 Sep - 8 Sep

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Top Cortona Hotel Reviews

Villa Borgo San Pietro

10/10 Excellent

"The property is gorgeous. The rooms are very well done. The staff is exceptionally attentive. The breakfast was perfect. The pool was a comfortable temperature. It was very very clean.The only thing that was missing was a full length mirror. It absolutely was perfecto."

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Unique and beautifully appointed hotel. We loved our stay here. The spa is lovely and the food was fabulous. The staff are wonderful especially Allesandro, Federico, Orlando, Matteo and all the lovely staff at breakfast. The housekeeping staff were very friendly and we had an amazing time here. We stayed for 10 nights so got to know Cortona and the surrounding area very well."

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"It was a spectacular stay and so peaceful! All the staff were super helpful and the quality of service, amenities, and food really shined. Before we actually arrived, the staff would check in with us leading up to make sure we were all set up and all our requests answered. They also helped us prepare a wonderful birthday surprise for someone in our party."

"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."

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

5. Farmhouse with mountain views hot tub

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. Gorgeously restored tranquil farmhouse

13. Holiday Home 'La Casina All'angolo'

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 - Castagna" with Shared Pool and Wi-Fi

19. "Il Focolare" Superior Apartment in Monticchiello

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

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Villa Borgo San Pietro

Monastero di Cortona Hotel & Spa

Villa di Piazzano - Small Luxury Hotel of the World

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

A small cottage in authentic Tuscany. Serves 4

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort Spa

Relais Villa Baldelli

Hotel San Luca

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

5. Farmhouse with mountain views hot tub

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. Gorgeously restored tranquil farmhouse

13. Holiday Home 'La Casina All'angolo'

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 - Castagna" with Shared Pool and Wi-Fi

19. "Il Focolare" Superior Apartment in Monticchiello

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

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Villa Borgo San Pietro