Cortona Holiday Rentals

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Our top choices for Cortona holiday 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
The price is AU$185
includes taxes & fees
3 Mar - 4 Mar
Vicolo Della Scala Rooms - Il Sole

Apartment in Cortona Old Town

Vicolo Della Scala Rooms - La Luna
The price is AU$180
includes taxes & fees
4 Mar - 5 Mar
Vicolo Della Scala Rooms - La Luna

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
The price is AU$245
includes taxes & fees
4 Mar - 5 Mar
La Locanda di San Francesco

Townhouse in Chiusi

La Piccola Locanda
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is AU$197
includes taxes & fees
15 Mar - 16 Mar
La Piccola Locanda

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (129 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste

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
Meublé Il Riccio

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
The price is AU$138
includes taxes & fees
17 Mar - 18 Mar
Abbadia Sicille Relais

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is AU$309
includes taxes & fees
6 Mar - 7 Mar
Casanova - Panoramic Rooms and Suites

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
The price is AU$302
includes taxes & fees
15 Mar - 16 Mar
Castello di Monterone

Condo in Vernazzano Basso

IL GIARDINO DELLE NINFE
The price is AU$403
includes taxes & fees
2 Mar - 3 Mar
IL GIARDINO DELLE NINFE

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is AU$285
includes taxes & fees
3 Mar - 4 Mar
Delcorto Suites

Residence in Monte San Savino

Castello di Gargonza
3.0 star property
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
Castello di Gargonza

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
The price is AU$129
includes taxes & fees
6 Mar - 7 Mar
Artisti del Cavallo Tourism

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
Affitacamere Maria Gabriella
Luxury resort in the Tuscan countryside

Residence in Montalcino

Borgo Lucignanello Bandini
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is AU$507
includes taxes & fees
9 Mar - 10 Mar
Borgo Lucignanello Bandini

Townhouse in Corciano

L'Antica Sosta
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is AU$98
includes taxes & fees
4 Mar - 5 Mar
L'Antica Sosta

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 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
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cortona holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cortona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cortona holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona holiday 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 holiday.

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 holiday rentals in Cortona?

Yes, there are holiday rentals close to the most popular sights in Cortona, or you can select a more 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 theatre during your trip.

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

Beautiful tuscan villa with pool, ideal for groups: This highly rated holiday home rental in Cortona is located in the mountains, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. 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 holiday rentals are there in Cortona?

With 151 Expedia holiday rentals, you're guaranteed 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 holiday rental in Cortona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cortona. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.