Cortona Vacation Homes from ￥12,426

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.

￥17,989 total

includes taxes & fees

Sep 3 - Sep 4

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

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

Cortona

￥15,022 total

includes taxes & fees

Aug 30 - Aug 31

3. Hillside home in an ancient Camaldolese hamlet

Cortona

￥81,943 total

includes taxes & fees

Sep 19 - Sep 20

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

4. Farmhouse with mountain views hot tub

Cortona

￥73,576 total

includes taxes & fees

Aug 31 - Sep 1

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

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

Cortona

￥56,567 total

includes taxes & fees

Aug 30 - Aug 31

A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

6. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

￥12,426 total

includes taxes & fees

Sep 1 - Sep 2

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

7. Dolce Casa 2 by Tiny Away

Rigutino

￥19,796 total

includes taxes & fees

Aug 31 - Sep 1

8. Dolce Casa 1 by Tiny Away

Rigutino

￥20,965 total

includes taxes & fees

Aug 31 - Sep 1

A brick building with a large sliding glass door, a brown door, and a small potted plant.

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

Foiano della Chiana

￥14,991 total

includes taxes & fees

Sep 1 - Sep 2

A narrow street with buildings on either side, stone walls, and a clear blue sky.

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

Arezzo Centro Storico

Maria Gemma

￥27,263 total

includes taxes & fees

Sep 4 - Sep 5

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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

Toscana

￥29,860 total

includes taxes & fees

Aug 31 - Sep 1

A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

12. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

￥24,407 total

includes taxes & fees

Aug 31 - Sep 1

A thatched-roof pavilion overlooking a calm lake with distant mountains.

13. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

Nigel G.

￥56,997 total

includes taxes & fees

Sep 1 - Sep 2

A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

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

￥39,411 total

includes taxes & fees

Sep 4 - Sep 5

A narrow pathway leading to a building with a tree in the center, surrounded by greenery.

15. LANDLORD ALBACHIARA

Ramazzano - Le Pulci

Fabio

￥22,088 total

includes taxes & fees

Sep 8 - Sep 9

A kitchen with a tiled backsplash and three hanging utensils.

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

Castiglione del Lago

￥26,892 total

includes taxes & fees

Sep 2 - Sep 3

A stone building with a balcony, outdoor seating, and a stone staircase.

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

lisciano niccone

￥78,231 total

includes taxes & fees

Sep 1 - Sep 2

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

lisciano niccone

Anonymous traveler

￥68,542 total

includes taxes & fees

Sep 8 - Sep 9

A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

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

Lisciano Niccone

Anonymous traveler

￥81,115 total

includes taxes & fees

Sep 3 - Sep 4

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

Anghiari

￥18,546 total

includes taxes & fees

Aug 31 - Sep 1

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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."

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews	14
Accommodation	221 Vacation Homes
Lowest Price	￥12,426
Highest Price	￥81,943

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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

A small cottage in authentic Tuscany. Serves 4

Cortona Resort Spa

Relais Villa Baldelli

Hotel San Michele

Villa di Piazzano - Small Luxury Hotel of the World

Locanda agli Amici

Hotel San Luca

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

Villa Santa Margherita

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. 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

A small cottage in authentic Tuscany. Serves 4

Find out more about Cortona

Cortona Vacation Homes information

Explore a world of travel with Expedia