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 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

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
$92 nightly
The price is $92
Jun 28 - Jun 29
Total with taxes and fees
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.
$106 nightly
The price is $111
Jul 2 - Jul 3
Total with taxes and fees
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
$103 nightly
The price is $118
Jul 1 - Jul 2
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole
Deluxe Apartment, City View | Soundproofing, iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
$127 nightly
The price is $143
Jul 4 - Jul 5
Total with taxes and fees
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.
$115 nightly
The price is $119
Jul 19 - Jul 20
Total with taxes and fees
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
$292 nightly
The price is $297
Jun 28 - Jun 29
Total with taxes and fees
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
$3,643 nightly
The price is $3,666
Jul 7 - Jul 8
Total with taxes and fees
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
$130 nightly
The price is $147
Jun 29 - Jun 30
Total with taxes and fees
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.
$223 nightly
The price is $227
Jun 28 - Jun 29
Total with taxes and fees
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.
$110 nightly
The price is $116
Jul 2 - Jul 3
Total with taxes and fees
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
$342 nightly
The price is $347
Jun 28 - Jun 29
Total with taxes and fees
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
$210 nightly
The price is $216
Jul 12 - Jul 13
Total with taxes and fees
B&B Casa Fattorini Apartment Bernie
Living area

B&B Casa Fattorini Apartment Ada

B&B Casa Fattorini Apartment Ada
Toscana
$235 nightly
The price is $235
Jul 9 - Jul 10
Total with taxes and fees
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
$161 nightly
The price is $164
Jun 29 - Jun 30
Total with taxes and fees
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
$413 nightly
The price is $419
Jul 2 - Jul 3
Total with taxes and fees
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
$6,038 nightly
The price is $6,038
Jul 20 - Jul 21
Total with taxes and fees
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
$1,665 nightly
The price is $1,670
Jun 29 - Jun 30
Total with taxes and fees
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
$164 nightly
The price is $170
Jun 29 - Jun 30
Total with taxes and fees
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
$444 nightly
The price is $450
Jun 28 - Jun 29
Total with taxes and fees
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
$115 nightly
The price is $119
Jun 28 - Jun 29
Total with taxes and fees
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"This was my favorite place we stayed in Italy. The property is immaculate and convenient to the city square. The staff were all so kind, professional, and personable. We loved the spa, the beautiful pool, the views, the cocktail bar on site. We will be back."
Erin 2-night trip
Posted 7 days ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Everything you need to know about Cortona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cortona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cortona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cortona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cortona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cortona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.