Cortona Vacation Rentals

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Our top choices for Cortona vacation rentals

Townhouse in Cortona Old Town

B&B Piccolo Hotel
9.4 out of 10, Exceptional, (20 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
B&B Piccolo Hotel

Apartment in Cortona Old Town

Vicolo Della Scala Rooms - Il Sole
$116 nightly
The price is $130
Mar 6 - Mar 7
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole

Apartment in Cortona Old Town

Vicolo Della Scala Rooms - La Luna
$112 nightly
The price is $126
Mar 13 - Mar 14
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (88 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
$162 nightly
The price is $183
Mar 16 - Mar 17
Total with taxes and fees
Meublé Il Riccio

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (133 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
$170 nightly
The price is $192
Mar 5 - Mar 6
Total with taxes and fees
La Locanda di San Francesco

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (180 reviews)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
$86 nightly
The price is $102
Mar 8 - Mar 9
Total with taxes and fees
Cameracaffè Centro

Residence in Perugia

Castello di Monterone
9.8 out of 10, Exceptional, (304 reviews)
"Staff was great, the castle itself is incredible."
United States
Kevin
$138 nightly
The price is $157
Mar 5 - Mar 6
Total with taxes and fees
Castello di Monterone

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134 reviews)
"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"
Canada
Mark
$134 nightly
The price is $155
Mar 5 - Mar 6
Total with taxes and fees
Hotel San Gregorio

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
$132 nightly
The price is $149
Mar 17 - Mar 18
Total with taxes and fees
Affitacamere Maria Gabriella

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
$93 nightly
The price is $107
Mar 5 - Mar 6
Total with taxes and fees
PienzaLettings Suites

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (129 reviews)
"Great hosts, central location "
United States
Alexander
$112 nightly
The price is $128
Mar 8 - Mar 9
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (168 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
$87 nightly
The price is $100
Mar 17 - Mar 18
Total with taxes and fees
Abbadia Sicille Relais

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1 review)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
$93 nightly
The price is $107
Mar 5 - Mar 6
Total with taxes and fees
TuscanyLettings Studio&Room

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
$178 nightly
The price is $200
Mar 5 - Mar 6
Total with taxes and fees
Delcorto Suites

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
$83 nightly
The price is $94
Mar 5 - Mar 6
Total with taxes and fees
Artisti del Cavallo Tourism

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
$85 nightly
The price is $99
Mar 9 - Mar 10
Total with taxes and fees
Residenza Fabroni

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$95 nightly
The price is $109
Mar 23 - Mar 24
Total with taxes and fees
DormiVeglia B&B

Townhouse in Arezzo

THE MONNA LISA RESORT
9.2 out of 10, Wonderful, (9 reviews)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
THE MONNA LISA RESORT

Townhouse in Civitella in Val di Chiana

Locanda Antico Borgo
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
$115 nightly
The price is $127
Mar 6 - Mar 7
Total with taxes and fees
Locanda Antico Borgo

Townhouse in Cetona

La Locanda Di Cetona
9.4 out of 10, Exceptional, (6 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
$144 nightly
The price is $158
Mar 5 - Mar 6
Total with taxes and fees
La Locanda Di Cetona
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

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.

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?

Beautiful tuscan villa with pool, ideal for groups: Visitors give good reviews to this Cortona vacation home rental, which is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Some other top choices in Cortona are Pet friendly home in Cortona AR and Podere Casorbica with free parking, large garden, private pool..

How many vacation rentals are there in Cortona?

With 151 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 Villa Bramasole 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.