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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Top Holiday Rentals in Cortona

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Luxury Cortona view hilltop Villa
Outdoor dining

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa
Casina in authentic Tuscany
Exterior

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (66)
"This is a charming house in a small town outside Cortona. Easily located near all the things you would want to see in the area. The host treated us like family and had homemade treats and wine waiting for our arrival. The house is perfectly suited for 4 people to stay and had a lot of charm. If you are looking to escape the hustle of daily life and relax this is the perfect location. "
Casina in authentic Tuscany
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Property grounds

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

9.8 out of 10, Exceptional, (32)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
17th-century Tuscan villa, few km from Cortona!
Outdoor pool

17th-century Tuscan villa, few km from Cortona!

17th-century Tuscan villa, few km from Cortona!
Cortona Skyline Retreat
Outdoor dining

Cortona Skyline Retreat

10.0 out of 10, Exceptional, (1)
"We loved our stay. The house was very clean and had everything we could want. The location provides great access to the city and parking. And the host was very helpful with recommendations."
Cortona Skyline Retreat
Appartamento Loggetta
Apartment, 1 Bedroom | View from room

Appartamento Loggetta

Appartamento Loggetta
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This is a lovely property. Plenty of room. Well equipped with everything you need. The courtyard is a beautiful place for breakfast in the morning and wine in the evening. The flowers planted in the courtyard are beautiful. Please be aware that you must be able to walk up steep hills to get to this property. Of course, pretty much anywhere you go in Cortona is a hill."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (45)
"Great location in Tuscany! tight roads in and out of the property, must it has the most spectacular views around. 3 min. drive to Cortona.The villa is spacious and very accomodating. Just be sure to ask how to use the dishwasher and washing machine. "
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
The Old Fashion House
Smart TV

The Old Fashion House

10.0 out of 10, Exceptional, (7)
"My husband and I spent a week here in April. We have been to Italy seven times, always staying in VRBO-type rentals and this rental stands apart as among the nicest. Recently renovated, well-equipped kitchen, balcony, comfortable heat, etc. You can see the owner, Giovanni, took great care with the design and remodeling. The location is perfect — just off the main street. We highly recommend this home! "
The Old Fashion House
Charming Tuscan Retreat: Borgo La Fonte
Dining

Charming Tuscan Retreat: Borgo La Fonte

10.0 out of 10, Exceptional, (2)
"Lovely renovation on a very old Tuscan home! Wonderful amenities. Perfect location. Easy drive to Cortona. Hope to return in the future!"
Charming Tuscan Retreat: Borgo La Fonte
Tina's House
Dining

Tina's House

10.0 out of 10, Exceptional, (5)
"We loved the location and the size. It was very cozy and the owner was so gracious and communicative. I haven't had a better host even in the states. Would come back for sure to this same place. "
Tina's House
Nice apartment for 6 guests with pool, WIFI, TV and parking
Outdoor dining

Nice apartment for 6 guests with pool, WIFI, TV and parking

10.0 out of 10, Exceptional, (5)
"Un séjour enchanteur avec un lieu merveilleux pour découvrir les beautés de la Toscane et de l Ombrie. Une pensée particulière pour Piero et Louisa qui ont contribué par leur gentillesse, leur écoute à faire de notre séjour un moment que nous n oublieront pas. Mille Grazie Valerie Olivier Richard Carole [English translation courtesy of Easy Reserve] An enchanting stay in a wonderful place to discover the beauties of Tuscany and Umbria. A special thought for Piero and Louisa who contributed...
Nice apartment for 6 guests with pool, WIFI, TV and parking
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

10.0 out of 10, Exceptional, (2)
"The home is beautiful: Wonderfully decorated and lovingly cared for. Views are amazing; Caretakers are lovely and we all fell in love with Zorro the Dog. My only complaint is that the beds were only box springs and could have been more comfortable."
I Cipressi, 5 bedrooms with pool near Cortona
Casale Le Vigne, 8 pax, private pool
Dining

Casale Le Vigne, 8 pax, private pool

10.0 out of 10, Exceptional, (9)
"Group of 9 had a fantastic stay. The villa is superbly fitted out with lovely decor and kitchen equipment. The kids loved the pool as did the adults and the evening meal area was superb. Very good communication with the host who gave us some great suggestions. Loved our holiday and the villa was exactly what we needed. Very secluded so loved watching the stars with lots of local wine."
Casale Le Vigne, 8 pax, private pool
Prestigious apartment with panoramic terrace, located in the center of Cortona.
Fridge, microwave, oven, dishwasher

Prestigious apartment with panoramic terrace, located in the center of Cortona.

9.8 out of 10, Exceptional, (10)
"This was a beautiful apartment centrally located in the middle of town. Great restaurants nearby. La Loggetta was one of the best restaurants we ate at in our entire five weeks here in Italy.Had a wonderful time over the Easter weekend. The town was very festive and busy."
Prestigious apartment with panoramic terrace, located in the center of Cortona.
City / Village Apartment in Cortona with 2 bedrooms sleeps 6
Dining

City / Village Apartment in Cortona with 2 bedrooms sleeps 6

9.8 out of 10, Exceptional, (9)
"Spacious clean and well located apartment. Wonderful."
City / Village Apartment in Cortona with 2 bedrooms sleeps 6
Appartamento La Piazzetta
Property grounds

Appartamento La Piazzetta

9.8 out of 10, Exceptional, (9)
"Beautiful, magical, would do it again in a heartbeat!"
Appartamento La Piazzetta
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
Pool

La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

7.4 out of 10, Good, (3)
"Fascinating site, beautiful nature. Once obviously a well designed location, now somehow run down. Several things in the house and the surrounding are lft behind and broken.Its better to bring with you all you need in case you won't drive the car too often. The accsess takes time and needs a careful driver Communication with agency was always very prompt. Bring toilett paper, dish towels and soap with you....kitchen is small for more than 6 people in case you like to cook not only pasta. I...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
La Torretta - downtown Cortona, on the second floor of a noble palazzo
Microwave, oven, dishwasher, coffee/tea maker

La Torretta - downtown Cortona, on the second floor of a noble palazzo

10.0 out of 10, Exceptional, (4)
"Very roomy, well equipped, and a really good location. Would stay again!"
La Torretta - downtown Cortona, on the second floor of a noble palazzo
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

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, apart-hotels, 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 favorite 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 depends 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 you might find 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Agriturismo Borgo Spagnoli: This holiday home rental outside Cortona is located in a regional park, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. Kick off your shoes and enjoy yourself with a rooftop terrace and a private garden. Other favourite homes for rent in Cortona are Casa Bacco - private house with a remarkable garden in the centre of Cortona and Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream" .

How many holiday rentals are there in Cortona?

With 284 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 Cortona Cathedral 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.