Cortona Vacation Homes from ￥13,129

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

￥14,771 total

includes taxes & fees

Sep 9 - Sep 10

2. Montecchio di Cortona

Montecchio

Monica S.

￥17,688 total

includes taxes & fees

Aug 19 - Aug 20

3. Farmhouse with mountain views hot tub

Cortona

￥72,347 total

includes taxes & fees

Aug 21 - Aug 22

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

Cortona

￥55,622 total

includes taxes & fees

Aug 16 - Aug 17

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

Anghiari

￥16,412 total

includes taxes & fees

Sep 2 - Sep 3

6. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

￥13,129 total

includes taxes & fees

Sep 1 - Sep 2

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

Arezzo Centro Storico

Maria Gemma

￥25,804 total

includes taxes & fees

Aug 11 - Aug 12

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

Foiano della Chiana

￥15,741 total

includes taxes & fees

Aug 11 - Aug 12

9. Dolce Casa 2 by Tiny Away

Rigutino

￥19,498 total

includes taxes & fees

Aug 12 - Aug 13

10. Dolce Casa 1 by Tiny Away

Rigutino

￥20,635 total

includes taxes & fees

Aug 17 - Aug 18

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

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

Toscana

￥29,542 total

includes taxes & fees

Aug 11 - Aug 12

12. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

￥23,998 total

includes taxes & fees

Aug 31 - Sep 1

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

Castiglione del Lago

Bin L.

￥26,442 total

includes taxes & fees

Sep 9 - Sep 10

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

Antria

￥29,178 total

includes taxes & fees

Aug 11 - Aug 12

15. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

￥55,339 total

includes taxes & fees

Sep 1 - Sep 2

16. LANDLORD ALBACHIARA

Ramazzano - Le Pulci

Fabio

￥18,600 total

includes taxes & fees

Aug 11 - Aug 12

17. 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

￥42,034 total

includes taxes & fees

Aug 16 - Aug 17

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

Pieve Vecchia

Darren B.

￥74,950 total

includes taxes & fees

Aug 24 - Aug 25

Coffee/tea maker, fridge, microwave, oven

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

foiano

￥200,153 total

includes taxes & fees

Aug 17 - Aug 18

20. Agritourism in val d'orcia

montalcino

￥61,091 total

includes taxes & fees

Aug 11 - Aug 12

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Everything was absolutely perfect and we would happily go back."

"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!"

Cortona Resort Spa

10/10 Excellent

"Pro: gorgeous and spacious property, we were upgraded to a junior suite that was lovely, attentive staff, and incredible amenities. Pool was wonderful for tired bodies. Con: very few. The restaurant on site has pretty limited menu, toilet in room kept running all night long- informed staff on checkout (as it was troublesome to flush, and wasting water), fridge in room- housed in a cabinet that I feel caused it to overheat… and therefore was not very powerful enough to keep drinks cold. Loved this place and the attentive staff. Super friendly and wonderful hospitality."

Heritage Tuscan Farmhouse with private swimming pool

10/10 Excellent

"A beautiful farmhouse that exceeded all expectations! The location was amazing…. Cortona only 10 minutes drive was beautiful. Wine tasting in Montepulciano (45 mins away) amazing. We also took the train for a day in Florence!! Louise was a wonderful host and very responsive helping with recommendations and bookings!Nothing more to say except the pool on a hot day was sublime!!"

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews	11
Accommodation	221 Vacation Homes
Lowest Price	￥13,129
Highest Price	￥200,153

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

6. Happy Nest Tuscany Between Florence and Rome

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

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

9. Dolce Casa 2 by Tiny Away

10. Dolce Casa 1 by Tiny Away

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

12. Holiday Home 'La Casina All'angolo'

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

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

15. Gorgeously restored tranquil farmhouse

16. LANDLORD ALBACHIARA

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

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

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

20. Agritourism in val d'orcia

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Hotel San Luca

Hotel San Michele

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

Relais Villa Baldelli

A small cottage in authentic Tuscany. Serves 4

Cortona Resort Spa

Heritage Tuscan Farmhouse with private swimming pool

Locanda agli Amici

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

6. Happy Nest Tuscany Between Florence and Rome

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

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

9. Dolce Casa 2 by Tiny Away

10. Dolce Casa 1 by Tiny Away

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

12. Holiday Home 'La Casina All'angolo'

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

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

15. Gorgeously restored tranquil farmhouse

16. LANDLORD ALBACHIARA

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

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

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

20. Agritourism in val d'orcia

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Vacation Homes information

Explore a world of travel with Expedia