Cortona Vacation Homes from ￥74,548

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

￥14,757 total

includes taxes & fees

Sep 5 - Sep 6

2. Montecchio di Cortona

Montecchio

Monica S.

￥17,672 total

includes taxes & fees

Aug 19 - Aug 20

3. Farmhouse with mountain views hot tub

Cortona

￥72,437 total

includes taxes & fees

Aug 9 - Aug 10

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

Cortona

￥55,692 total

includes taxes & fees

Aug 16 - Aug 17

5. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

￥13,118 total

includes taxes & fees

Sep 4 - Sep 5

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

Foiano della Chiana

￥15,761 total

includes taxes & fees

Aug 11 - Aug 12

7. Dolce Casa 2 by Tiny Away

Rigutino

￥19,467 total

includes taxes & fees

Aug 18 - Aug 19

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

Arezzo Centro Storico

Maria Gemma

￥25,781 total

includes taxes & fees

Aug 13 - Aug 14

9. Dolce Casa 1 by Tiny Away

Rigutino

￥20,602 total

includes taxes & fees

Aug 18 - Aug 19

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

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

Toscana

￥29,333 total

includes taxes & fees

Aug 15 - Aug 16

11. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

￥23,977 total

includes taxes & fees

Sep 4 - Sep 5

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

Antria

￥29,151 total

includes taxes & fees

Aug 15 - Aug 16

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

Castiglione del Lago

Bin L.

￥26,475 total

includes taxes & fees

Sep 6 - Sep 7

14. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

￥55,424 total

includes taxes & fees

Sep 1 - Sep 2

15. -2 / 3-seater garage with private garden, swimming pool, park and spa

sansepolcro (arezzo)

Margit H.

￥28,057 total

includes taxes & fees

Sep 4 - Sep 5

16. LANDLORD ALBACHIARA

Ramazzano - Le Pulci

Fabio

￥19,731 total

includes taxes & fees

Aug 12 - Aug 13

17. Stunning villa for 6 people with A/C, WIFI, TV, balcony and panoramic view

Perugia

￥36,626 total

includes taxes & fees

Aug 28 - Aug 29

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

Pieve Vecchia

Darren B.

￥83,444 total

includes taxes & fees

Aug 24 - Aug 25

19. Romantic farm in the Sienese hills

Trequanda, Siena

"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...

Harald B.

￥39,987 total

includes taxes & fees

Aug 23 - Aug 24

20. Agritourism in val d'orcia

montalcino

￥61,581 total

includes taxes & fees

Aug 19 - Aug 20

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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."

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews	5
Accommodation	221 Vacation Homes
Lowest Price	￥74,548
Highest Price	￥74,548

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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. Happy Nest Tuscany Between Florence and Rome

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

7. Dolce Casa 2 by Tiny Away

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

9. Dolce Casa 1 by Tiny Away

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

11. Holiday Home 'La Casina All'angolo'

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

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

14. Gorgeously restored tranquil farmhouse

15. -2 / 3-seater garage with private garden, swimming pool, park and spa

16. LANDLORD ALBACHIARA

17. Stunning villa for 6 people with A/C, WIFI, TV, balcony and panoramic view

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

19. Romantic farm in the Sienese hills

20. Agritourism in val d'orcia

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

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

Villa di Piazzano - Small Luxury Hotel of the World

Cortona Resort Spa

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. Happy Nest Tuscany Between Florence and Rome

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

7. Dolce Casa 2 by Tiny Away

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

9. Dolce Casa 1 by Tiny Away

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

11. Holiday Home 'La Casina All'angolo'

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

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

14. Gorgeously restored tranquil farmhouse

15. -2 / 3-seater garage with private garden, swimming pool, park and spa

16. LANDLORD ALBACHIARA

17. Stunning villa for 6 people with A/C, WIFI, TV, balcony and panoramic view

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

19. Romantic farm in the Sienese hills

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