Holiday Homes in Cortona

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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 NZ$148
includes taxes & fees
14 Nov - 15 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 NZ$179
includes taxes & fees
14 Dec - 15 Dec
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 NZ$802
includes taxes & fees
13 Dec - 14 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 NZ$238
includes taxes & fees
14 Nov - 15 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, (2 reviews)
"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 NZ$1,067
includes taxes & fees
16 Nov - 17 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 NZ$1,829
includes taxes & fees
15 Nov - 16 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 NZ$195
includes taxes & fees
15 Nov - 16 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 NZ$161
includes taxes & fees
16 Nov - 17 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 NZ$206
includes taxes & fees
15 Nov - 16 Nov
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 NZ$193
includes taxes & fees
14 Nov - 15 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 NZ$337
includes taxes & fees
15 Nov - 16 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 NZ$289
includes taxes & fees
18 Nov - 19 Nov
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 NZ$305
includes taxes & fees
16 Nov - 17 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

14. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is NZ$546
includes taxes & fees
22 Nov - 23 Nov
Arc two-bedroom apartment

15. "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 NZ$229
includes taxes & fees
9 Dec - 10 Dec
"Il Focolare" Superior Apartment in Monticchiello

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 NZ$246
includes taxes & fees
19 Nov - 20 Nov
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

17. 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 NZ$5,385
includes taxes & fees
13 Dec - 14 Dec
Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

18. 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 NZ$1,359
includes taxes & fees
13 Dec - 14 Dec
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

19. Holiday Home 'La Limonaia' with Pool, Private Terrace and Wi-Fi

Holiday Home 'La Limonaia' with Pool, Private Terrace and Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"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...
Canada
Anonymous traveller
The price is NZ$404
includes taxes & fees
16 Nov - 17 Nov
Holiday Home 'La Limonaia' with Pool, Private Terrace and Wi-Fi

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 NZ$1,200
includes taxes & fees
22 Nov - 23 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.

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