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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Cortona vacation homes

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

1. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is AED 260
AED 334 total
includes taxes & fees
26 Oct - 27 Oct
Vacation home with a panoramic terrace, ideal for families and couples
Dining

2. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AED 326
AED 400 total
includes taxes & fees
28 Oct - 29 Oct
Montecchio di Cortona
A building with a stone facade, multiple windows, and a balcony.

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

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is AED 1,375
AED 1,546 total
includes taxes & fees
25 Oct - 26 Oct
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

4. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is AED 503
AED 519 total
includes taxes & fees
22 Nov - 23 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

5. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: The spaciousness of the modern house was perfect. We felt right at home. The big pool was highly appreciated. Cons: -"
United States
Anonymous traveler
The price is AED 1,990
AED 2,162 total
includes taxes & fees
1 Nov - 2 Nov
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

6. Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
The price is AED 4,152
AED 4,324 total
includes taxes & fees
25 Oct - 26 Oct
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
A window with lace curtains, a view of a building, and a wooden shelf with potted plants.

7. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is AED 185
AED 276 total
includes taxes & fees
24 Oct - 25 Oct
Happy Nest Tuscany Between Florence and Rome
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

8. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is AED 278
AED 402 total
includes taxes & fees
25 Oct - 26 Oct
Dolce Casa 2 by Tiny Away
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

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is AED 317
AED 333 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Room

10. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is AED 302
AED 425 total
includes taxes & fees
25 Oct - 26 Oct
Dolce Casa 1 by Tiny Away
A staircase with wooden steps and metal handrails, leading to an upper floor.

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

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is AED 295
AED 608 total
includes taxes & fees
8 Nov - 9 Nov
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
An outdoor patio with a wooden table and chairs, surrounded by a wooden pergola, and a view of greenery.

12. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is AED 544
AED 651 total
includes taxes & fees
31 Oct - 1 Nov
Holiday Home 'La Casina All'angolo'
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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

Double room with private bathroom in the countryside, 5 minutes from Montepulciano
Toscana
The price is AED 445
AED 668 total
includes taxes & fees
24 Oct - 25 Oct
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

14. La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
Castel Rigone
10.0 out of 10, Exceptional, (4 reviews)
"The place was amazing and as advertised! We enjoyed the area very much, the views are amazing! We shopped at the local market and enjoyed dinner in both nights we were there. If we are back in the area, we will stay here again! Saverio was very attentive and gracious. Check in and out couldn’t have been easier! "
United States
John L.
The price is AED 363
AED 537 total
includes taxes & fees
25 Oct - 26 Oct
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
A patio area with a table and chairs, a wooden pergola, and a view of a kitchen.

15. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is AED 948
AED 1,129 total
includes taxes & fees
14 Nov - 15 Nov
Arc two-bedroom apartment
A bedroom with a bed, nightstand, and a painting on the wall.

16. Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
Castiglion Fiorentino
The price is AED 2,136
AED 2,816 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

17. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveler
The price is AED 1,314
AED 1,322 total
includes taxes & fees
29 Oct - 30 Oct
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

18. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveler
The price is AED 598
AED 820 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Home in Villa Pandolfina near Montepulciano
A stone building with a balcony, outdoor seating, and a stone staircase.

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

Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
lisciano niccone
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Alles perfect in orde."
Netherlands
Anonymous traveler
The price is AED 1,725
AED 1,733 total
includes taxes & fees
29 Oct - 30 Oct
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
A stone building with a balcony, outdoor seating, and a stone staircase.

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

Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
lisciano niccone
The price is AED 1,156
AED 1,164 total
includes taxes & fees
29 Oct - 30 Oct
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Amazing service and care. Especially Sara, Mathilda, Fredrico and Allesandro. The manager was so helpful as well. A must stay!"
Karim 4-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa