Holiday Rentals in Cortona

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Cortona

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, (35)
"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
Appartamento Loggetta
Apartment, 1 Bedroom | View from room

Appartamento Loggetta

Appartamento Loggetta
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)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Luxury Cortona view hilltop Villa
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (12)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Beautiful villa with spectacular views in a rural location
Outdoor pool

Beautiful villa with spectacular views in a rural location

9.8 out of 10, Exceptional, (42)
"Absolutely stunning location and lovely house. We loved our week here. X"
Beautiful villa with spectacular views in a rural location
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
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
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.

10.0 out of 10, Exceptional, (11)
"Magnificent stay in a beautiful home. Perfect location for a few days in Cortona. Highlight of our trip"
Prestigious apartment with panoramic terrace, located in the center of Cortona.
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
Casale Le Vigne, 8 pax, private pool
Dining

Casale Le Vigne, 8 pax, private pool

10.0 out of 10, Exceptional, (10)
"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
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
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
Fratta Orchidee, Cortona, Italy
Fridge, oven, stovetop, dishwasher

Fratta Orchidee, Cortona, Italy

6.0 out of 10, (2)
"Location correcte mais qui nécessite plus d’investissement du propriétaire pour assurer le confort et la satisfaction des clients. Par exemple une location louée pour 6 personnes mériterait au moins 12 couverts complets ainsi que du nécessaire adéquat pour la cuisine. Le mobilier devrait aussi être entretenu, chaise cassée à l’arrivée, tringle à rideau qui tombe etc. Durant le séjour la piscine n’a pas suffisamment été entretenue et elle a tournée, il a fallu que j’appelle au bout de 24h pour...
Fratta Orchidee, Cortona, Italy
Casina in authentic Tuscany
Exterior

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (68)
"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
Heritage Tuscan Farmhouse with private swimming pool
Pool

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (48)
"Beautiful location. Great base to visit Cortona, Montepulciano, Siena, and Florence. Louise was wonderful and helpful. Thoroughly enjoyed our stay. "
Heritage Tuscan Farmhouse with private swimming pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

10.0 out of 10, Exceptional, (67)
"Very nice house well appointed updated air conditioning in every room nice pool big yard for kids very nice place to stay for a family vacation. Everyone had their own bed. We had 12 in our group. We stayed a month and it was fantastic."
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Pool

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

10.0 out of 10, Exceptional, (42)
"Lovely stay. Enjoyed the home, area, and local restaurants. Would stay again. "
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
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)
"Everything was perfect and we had plent of room. Highly recommend. "
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Cottage " I due Pini"
Outdoor dining

Cottage " I due Pini"

10.0 out of 10, Exceptional, (43)
"I due Pini cottage is a lovely place to relax. We received a very friendly and warm welcome. We get support and tips on all our questions. The house is very cozy and well equipped and has a terrace with beautiful views over the countryside. Thank you very much!"
Cottage " I due Pini"
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

Cortona Resort Spa

Cortona Resort Spa

8/10 Good
"Needs lotion in the guest rooms and towels. The staff was wonderful. So was the food. "
Candice 2-night trip
Posted 5 days ago
Cortona Resort Spa

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. 

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.

How many holiday rentals are there in Cortona?

With 279 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.