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

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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

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 ￥12,431
￥15,628 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥14,030
￥17,227 total
includes taxes & fees
Oct 19 - Oct 20
Montecchio di Cortona
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 ￥27,171
￥31,788 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥59,257
￥66,643 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥22,740
￥23,450 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.

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 ￥95,293
￥102,679 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.

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

Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
The price is ￥178,935
￥186,321 total
includes taxes & fees
Oct 19 - Oct 20
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

8. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,992
￥11,899 total
includes taxes & fees
Oct 19 - Oct 20
Happy Nest Tuscany Between Florence and Rome
A two-story residential building with a balcony and a small porch.

9. 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 ￥92,063
￥121,365 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
A brick building with a large sliding glass door, a brown door, and a small potted plant.

10. 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 ￥13,644
￥14,354 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

11. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥16,026
￥21,349 total
includes taxes & fees
Nov 3 - Nov 4
Dolce Casa 2 by Tiny Away
Room

12. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥17,343
￥22,666 total
includes taxes & fees
Oct 25 - Oct 26
Dolce Casa 1 by Tiny Away
A narrow street with buildings on either side, stone walls, and a clear blue sky.

13. 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 ￥12,698
￥26,195 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.

14. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥23,442
￥28,060 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.

15. 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 ￥19,180
￥28,592 total
includes taxes & fees
Oct 19 - Oct 20
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.

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 ￥15,663
￥23,121 total
includes taxes & fees
Oct 21 - Oct 22
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.

17. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is ￥40,846
￥48,660 total
includes taxes & fees
Nov 14 - Nov 15
Arc two-bedroom apartment
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

18. 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 ￥59,937
￥60,292 total
includes taxes & fees
Nov 17 - Nov 18
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A stone building with a balcony, outdoor seating, and a stone staircase.

19. 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 ￥49,814
￥50,169 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

20. 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 ￥25,751
￥35,341 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home in Villa Pandolfina near Montepulciano
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

Relais Villa Baldelli

Relais Villa Baldelli

10/10 Excellent
"Wonderful character and feel. The property for 100 AD, has been well renovated and maintained. Excellent staff 👏"
Ravi 4-night trip
Posted 11 hours ago
Relais Villa Baldelli

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
31
Accommodation
222 Vacation Homes
Lowest Price
￥11,899
Highest Price
￥186,321