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

Cortona Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 CA $99
CA $127 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $124
CA $152 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $513
CA $578 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $181
CA $187 total
includes taxes & fees
Nov 2 - Nov 3
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 traveller
The price is CA $758
CA $823 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $1,491
CA $1,556 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $71
CA $105 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $106
CA $154 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $121
CA $127 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $115
CA $162 total
includes taxes & fees
Oct 28 - Oct 29
Dolce Casa 1 by Tiny Away
A rustic brick building with a mural, a clock, and various potted plants.

11. 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 CA $110
CA $144 total
includes taxes & fees
Oct 27 - Oct 28
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A staircase with wooden steps and metal handrails, leading to an upper floor.

12. 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 CA $112
CA $231 total
includes taxes & fees
Nov 8 - Nov 9
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.

13. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is CA $186
CA $227 total
includes taxes & fees
Oct 31 - Nov 1
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.

14. 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 CA $169
CA $251 total
includes taxes & fees
Oct 27 - Oct 28
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A dining table set outdoors with a view of the sunset over a body of water.

15. 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 CA $138
CA $204 total
includes taxes & fees
Oct 27 - Oct 28
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.

16. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is CA $361
CA $430 total
includes taxes & fees
Nov 14 - Nov 15
Arc two-bedroom apartment
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.

17. 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 CA $813
CA $1,072 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
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 traveller
The price is CA $205
CA $289 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home in Villa Pandolfina near Montepulciano
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

19. "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 CA $157
CA $191 total
includes taxes & fees
Oct 29 - Oct 30
"Il Focolare" Superior Apartment in Monticchiello
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 CA $800
CA $803 total
includes taxes & fees
Oct 29 - Oct 30
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
"Beautiful historic property well located with just enough to do. Very relaxing ."
Peter 4-night trip
Posted 7 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
25
Accommodation
222 Vacation Homes
Lowest Price
CA $105
Highest Price
CA $1,556

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