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

Search Vacation Homes in Cortona

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Cortona vacation homes

Dining

1. 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 ￥13,953
￥17,132 total
includes taxes & fees
Oct 29 - Oct 30
Montecchio di Cortona
A park with picnic tables, a playground, and a gravel path.

2. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,171
￥14,363 total
includes taxes & fees
Oct 16 - Oct 17
Holiday home with panoramic terrace ideal for families and couples
A stone building with a patio area featuring outdoor furniture and potted plants.

3. Podere Casorbica with free parking, large garden, private pool.

Podere Casorbica with free parking, large garden, private pool.
cortona
9.6 out of 10, Exceptional, (18 reviews)
"Giorgio is very welcoming, the house has a very authentic feel. "
Netherlands
Joost B.
The price is ￥27,129
￥31,739 total
includes taxes & fees
Oct 16 - Oct 17
Podere Casorbica with free parking, large garden, private pool.
A building with a stone facade, multiple windows, and a balcony.

4. 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 ￥59,164
￥66,539 total
includes taxes & fees
Oct 18 - Oct 19
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

5. 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 ￥22,617
￥23,324 total
includes taxes & fees
Nov 5 - Nov 6
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

6. 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 ￥94,776
￥102,122 total
includes taxes & fees
Nov 5 - Nov 6
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

7. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,979
￥11,880 total
includes taxes & fees
Oct 16 - Oct 17
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 ￥16,696
￥22,010 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥13,623
￥14,332 total
includes taxes & fees
Oct 16 - Oct 17
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 ￥18,134
￥23,433 total
includes taxes & fees
Nov 2 - Nov 3
Dolce Casa 1 by Tiny Away
A narrow street with buildings on either side, stone walls, and a clear blue sky.

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 ￥12,678
￥26,154 total
includes taxes & fees
Nov 8 - Nov 9
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A kitchen counter with a coffee maker, a paper towel holder, and a window with 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 ￥23,405
￥28,015 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.

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 ￥19,076
￥28,614 total
includes taxes & fees
Nov 5 - Nov 6
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

14. 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 ￥56,518
￥56,873 total
includes taxes & fees
Oct 16 - Oct 17
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

15. Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
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 ￥15,578
￥22,997 total
includes taxes & fees
Oct 28 - Oct 29
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A stone building with a balcony, outdoor seating, and a stone staircase.

16. 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 ￥73,918
￥74,271 total
includes taxes & fees
Nov 15 - Nov 16
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

17. 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 ￥25,611
￥35,149 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Home in Villa Pandolfina near Montepulciano
A stone building with a balcony, outdoor seating, and a stone staircase.

18. 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 ￥49,736
￥50,091 total
includes taxes & fees
Oct 17 - Oct 18
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

19. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Vacation Home 'La Limonaia' with Pool, Private Terrace & 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 traveler
The price is ￥20,746
￥36,881 total
includes taxes & fees
Oct 16 - Oct 17
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
A stone building with a glass table and chairs, outdoor seating, and a staircase leading to an upper level.

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

Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi
Lisciano Niccone
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Everything"
United States
Anonymous traveler
The price is ￥71,533
￥71,886 total
includes taxes & fees
Nov 15 - Nov 16
Apartment 'Pugnano Alto- Girasole' 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Hotel San Luca

Hotel San Luca

8/10 Good
"Well located"
Frances 1-night trip
Posted 17 hours ago
Hotel San Luca

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
37
Accommodation
222 Vacation Homes
Lowest Price
￥11,880
Highest Price
￥102,122