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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Cortona vacation rentals

Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,600
￥14,914 total
includes taxes & fees
Jun 30 - Jul 1
Holiday home with panoramic terrace ideal for families and couples
Property grounds

City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is ￥17,216
￥17,953 total
includes taxes & fees
Jul 2 - Jul 3
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ￥16,899
￥19,326 total
includes taxes & fees
Jun 30 - Jul 1
Vicolo Della Scala Rooms - Il Sole
Deluxe Apartment, City View | Soundproofing, iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ￥20,789
￥23,420 total
includes taxes & fees
Jul 15 - Jul 16
CASA AMBRA
Pool

Apartment “Papà Giuseppe La Stalla” with Shared Pool and Wi-Fi

Apartment “Papà Giuseppe La Stalla” with Shared Pool and Wi-Fi
Cortona
2.0 out of 10, (1 review)
"Accoglienza a dir poco pessimaCasa poco pulitaAssenza del proprietario al nostro arrivoDifficoltà nell’individuazione della casaGuasto caldaia con problemi per soggiornoSiamo andati via senza poter restare a dormire "
Italy
Cristina M.
The price is ￥18,525
￥19,262 total
includes taxes & fees
Jul 19 - Jul 20
Apartment “Papà Giuseppe La Stalla” with Shared Pool and Wi-Fi
Exterior

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
The price is ￥40,420
￥48,078 total
includes taxes & fees
Jun 30 - Jul 1
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Outdoor dining

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Cortona
The price is ￥441,913
￥445,596 total
includes taxes & fees
Jul 7 - Jul 8
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥21,016
￥23,854 total
includes taxes & fees
Jun 30 - Jul 1
B&B Piccolo Hotel
Interior

La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (36 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is ￥24,029
￥36,550 total
includes taxes & fees
Jul 11 - Jul 12
La Finestra sul Teatro
Dining

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 ￥14,546
￥18,781 total
includes taxes & fees
Jun 30 - Jul 1
Montecchio di Cortona
Exterior

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 ￥48,504
￥56,162 total
includes taxes & fees
Jun 30 - Jul 1
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Interior

B&B Casa Fattorini Apartment Bernie

B&B Casa Fattorini Apartment Bernie
Toscana
The price is ￥29,829
￥34,985 total
includes taxes & fees
Jul 12 - Jul 13
B&B Casa Fattorini Apartment Bernie
Living area

B&B Casa Fattorini Apartment Ada

B&B Casa Fattorini Apartment Ada
Toscana
The price is ￥33,143
￥37,562 total
includes taxes & fees
Jul 12 - Jul 13
B&B Casa Fattorini Apartment Ada
Interior

Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is ￥22,740
￥26,606 total
includes taxes & fees
Jul 5 - Jul 6
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior

Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
9.4 out of 10, Exceptional, (3 reviews)
"Pros: Great house, pool, and location!! Thank you!"
United States
Anonymous traveler
The price is ￥60,225
￥67,883 total
includes taxes & fees
Jul 1 - Jul 2
Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning
Dining

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is ￥977,732
￥977,732 total
includes taxes & fees
Jun 30 - Jul 1
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Exterior

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

Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
The price is ￥516,351
￥524,009 total
includes taxes & fees
Jul 1 - Jul 2
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Exterior detail

Casa Beppina Cortona by Interhome

Casa Beppina Cortona by Interhome
Cortona Old Town
Casa Beppina Cortona by Interhome
Exterior

Apartment "Pilari Castagnolo" with Mountain View, Shared Pool & Wi-Fi

Apartment "Pilari Castagnolo" with Mountain View, Shared Pool & Wi-Fi
Cortona
The price is ￥75,493
￥76,414 total
includes taxes & fees
Jul 6 - Jul 7
Apartment "Pilari Castagnolo" with Mountain View, Shared Pool & Wi-Fi
Exterior detail

Vacation home Beppina, typical cortonese house, in the center, animals welcome

Vacation home Beppina, typical cortonese house, in the center, animals welcome
Cortona Old Town
The price is ￥15,344
￥19,306 total
includes taxes & fees
Jun 30 - Jul 1
Vacation home Beppina, typical cortonese house, in the center, animals welcome
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Staff was so friendly and the property is beautiful"
Niyome 2-night trip
Posted 13 hours ago
Villa di Piazzano - Small Luxury Hotel of the World

Find out more about Cortona

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday apartments in Cortona using one of the methods below:

  • View our selection of featured holiday rentals in Cortona
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  • Enter your travel dates to view the best deals on holiday rentals in Cortona while they last

Look no further and take a look at our great range of rental properties in Cortona!

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theater during your trip.

What are some of the best vacation home rentals that Cortona has to offer?

Podere Casorbica with free parking, large garden, private pool.: Visitors give good reviews to this Cortona vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a balcony and a garden. Some other top choices in Cortona are beautiful tuscan villa with pool, ideal for groups and Casa Bacco - private house with a remarkable garden in the centre of Cortona.

How many vacation rentals are there in Cortona?

With 143 Expedia vacation rentals, you're sure to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Cultural attractions include Museum of the Etruscan Academy and Signorelli Theatre, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Casali Palace are other places worth a visit.

What’s a vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.