Cortona Vacation Rentals from CA $956: Short-Term Rentals for 2025

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

Agriturismo Borgo Spagnoli : You might want to consider this Cortona vacation home rental for your stay. It is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill 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 yard. Other favorite homes for rent in Cortona are Casa Bacco - private house with a remarkable garden in the centre of Cortona and Podere Casorbica with free parking, large garden, private pool. .

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Vacation Rentals in Cortona

"Samantha’s apartment was wonderful! The terrace was dreamy, with views and sunsets that I will remember for a long time! Apertivos and evenings sitting outside were lovely! The location is quiet and convenient. Lacking only a few refinements, the apartment is very desirable. "

"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. "

"This is a lovely, updated home in a fantastic location to use as base for Tuscan/ Umbrian day trips. The town of Camucia has all conveniences, many within walking distance including groceries, restaurants and the train station (@ 10 min). Cortona is a short drive up the hill. We spent most evenings in the house and really appreciated the comfortable living area. The kitchen was well equipped for any meal but we mainly used it for morning coffee/breakfast. It was too early in the season to use...

"The villa was so comfortable and lovely. Michele was very responsive and helpful. 10/10 experience."

"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."

"This home was outstanding from the moment we arrived. There were 6 adults and we had plenty of room to gather together. The courtyard is lovely for early morning coffee or evening wine. Close to everything that Cortona offers."

"The property was lovely. Wifi was intermittently availble throughout our stay."

"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."

"We liked our stay very much"

"Everything’ we could have wished for. Wonderfully private Glorious garden Brilliant swimming pool Smiling and generous owner who could not do enough Incredibly helpful caretaker. Everything was excellent"

"We had a two week escape in the Tuscan countryside. We enjoyed touring around the area and a organized cooking class"

"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."

"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."

"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! "

"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. "

"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."

"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...

"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...

CA $1,333 total

includes taxes & fees

Aug 2 - Aug 3

Microwave, oven, dishwasher, coffee/tea maker

"Very roomy, well equipped, and a really good location. Would stay again!"

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Gorgeous hotel, very helpful and friendly staff, stunning pool and spa. Loved everything about this hotel! Just know that it’s an uphill walk to get there from the town center. "

Locanda agli Amici

10/10 Excellent

"An amazing property that is managed with love and care. The location was easy to find using Google Maps and we parked at the door. The view was spectacular, the service was incredible and the evening meal on the terrace was one of the best we have had. A refreshing pool and a 5 star breakfast buffet to set us up for the day. "

Hotel Italia

10/10 Excellent

"Had a great stay at Hotel Italia. On arrival, flight was delayed and train from Rome delayed but lovely lady on the front desk offered to stay until nearly 9pm so she could check me in which was hugely appreciated after such a busy day travelling! The room is big and airy, very tidy with a comfortable bed. Location is perfect being only a 30 second walk from the main Piazza. Already looking to book our next trip to Cortona and will be staying here again!"

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cortona vacation rentals we have selected for you start as low as CA $956 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 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.

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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?

Agriturismo Borgo Spagnoli: You might want to consider this Cortona vacation home rental for your stay. It is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill 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 yard. Other favorite homes for rent in Cortona are Casa Bacco - private house with a remarkable garden in the centre of Cortona and Podere Casorbica with free parking, large garden, private pool..

How many vacation rentals are there in Cortona?

With 286 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 Cortona Cathedral 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.

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Cortona Vacation Rentals

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Vacation Rentals in Cortona

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

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

Casina in authentic Tuscany

Casina in authentic Tuscany

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Cortona Skyline Retreat

Cortona Skyline Retreat

Appartamento Loggetta

Appartamento Loggetta

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

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

Podere Casorbica with free parking, large garden, private pool.

Podere Casorbica with free parking, large garden, private pool.

Luxury Cortona view hilltop Villa

Luxury Cortona view hilltop Villa

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

Private Villa with WIFI, private pool, A/C, patio, panoramic view, parking, close to Montepulciano

Private Villa with WIFI, private pool, A/C, patio, panoramic view, parking, close to Montepulciano

Casa Fontelunga, Tuscan holiday villa with private pool

Casa Fontelunga, Tuscan holiday villa with private pool

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

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

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

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

The Old Fashion House

The Old Fashion House

Tina's House

Tina's House

I Cipressi, 5 bedrooms with pool near Cortona

I Cipressi, 5 bedrooms with pool near Cortona

Cosy apartment for 6 people with WIFI, pool, TV and parking

Cosy apartment for 6 people with WIFI, pool, TV and parking

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

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

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

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Cortona

Find out more about Cortona

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