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Our top choices for Cortona holiday homes

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 HK$554
HK$651 total
includes taxes & fees
7 Nov - 8 Nov
Vacation home with a panoramic terrace, ideal for families and couples

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 HK$695
HK$791 total
includes taxes & fees
10 Nov - 11 Nov
Montecchio di Cortona

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 HK$3,203
HK$3,570 total
includes taxes & fees
30 Nov - 1 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

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 HK$1,013
HK$1,049 total
includes taxes & fees
7 Nov - 8 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

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 traveller
The price is HK$4,343
HK$4,709 total
includes taxes & fees
11 Nov - 12 Nov
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

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 HK$7,720
HK$8,087 total
includes taxes & fees
8 Nov - 9 Nov
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning

7. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is HK$597
HK$862 total
includes taxes & fees
8 Nov - 9 Nov
Dolce Casa 2 by Tiny Away

8. 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 HK$676
HK$711 total
includes taxes & fees
6 Nov - 7 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

9. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is HK$897
HK$1,162 total
includes taxes & fees
2 Dec - 3 Dec
Dolce Casa 1 by Tiny Away

10. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is HK$655
HK$852 total
includes taxes & fees
6 Nov - 7 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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 HK$629
HK$1,297 total
includes taxes & fees
8 Nov - 9 Nov
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

12. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is HK$1,164
HK$1,393 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Home 'La Casina All'angolo'

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 HK$950
HK$1,354 total
includes taxes & fees
8 Nov - 9 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

14. 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 HK$4,559
HK$6,009 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

15. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is HK$2,022
HK$2,409 total
includes taxes & fees
14 Nov - 15 Nov
Arc two-bedroom apartment

16. 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 HK$776
HK$1,083 total
includes taxes & fees
6 Nov - 7 Nov
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

17. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is HK$879
HK$1,011 total
includes taxes & fees
11 Nov - 12 Nov
"Il Focolare" Superior Apartment in Monticchiello

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

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is HK$9,651
HK$9,651 total
includes taxes & fees
7 Nov - 8 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

19. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
Lisciano Niccone
The price is HK$23,808
HK$23,826 total
includes taxes & fees
8 Nov - 9 Nov
Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

20. 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 traveller
The price is HK$4,485
HK$4,502 total
includes taxes & fees
6 Nov - 7 Nov
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
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.

Learn more about Cortona

Perched on a Tuscan hillside, this medieval town offers panoramic views from Piazza Garibaldi and Renaissance art in the Diocesan Museum. Climb to the Medici Fortress for sunset photos, then sample local wines and porcini dishes at family-run trattorias along Via Nazionale.

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