Cortona Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Cortona

Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"This is a wonderful property in a quiet area, but only a short walk to the piazza and restaurants. The only improvement I would recommend is the shower caddy; all of my travel sized items kept falling out of it."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Exterior
Podere Casorbica with free parking, large garden, swimming pool.
9.2 out of 10, Wonderful, (9)
"We are a family of five and found the property ideal for our needs, the children occupied the first floor whilst mum and dad occupied the ground floor, both have a kitchen area and lovely bathrooms with ample space to dine together on the ground floor. The property was clean and is very well maintained. The owner Giorgio met us on our arrival and managed to answer any questions we had with the help of google translate and actually came to the property every morning to clean the pool, this was...
Podere Casorbica with free parking, large garden, swimming pool.
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
La Finestra sul Teatro
9.8 out of 10, Exceptional, (29)
"This unit met and exceeded our expectations! The host was extremely friendly and helpful, and this well-stocked home has a perfect location within the best area of Cortona. I highly recommend this unit to anyone wishing for a clean, 'light & bright' home within walking distance to everything you would ever want to do here. Thank you, Rossana, for sharing your home with us, we look forward to our next visit!"
The price is HK$1,233
per night
2 Jun - 3 Jun
La Finestra sul Teatro
Fridge, microwave, oven, dishwasher
Prestigious apartment with panoramic terrace, located in the center of Cortona.
9.6 out of 10, Exceptional, (4)
"This is a great home, perfect location (close to parking and walk to everything) and really nice and thoughtful manager!!!"
Prestigious apartment with panoramic terrace, located in the center of Cortona.
View from property
Cortonas Rooftop Nest
10.0 out of 10, Exceptional, (6)
"Our recent stay in Cortona was pure bliss. The apartment boasted expansive views of the picturesque town, complemented by tasteful furnishings and a fully equipped, spacious kitchen. The Wi-Fi was top-notch, perfect for both work and leisure. Margherita, our charming host, was a delight. Fluent in English, she was always available and attentive to our needs. Highly recommend this gem for an unforgettable Tuscan experience."
The price is HK$1,259
per night
19 May - 20 May
Cortonas Rooftop Nest
Property grounds
Large independent villa with pool: privacy, absolute quiet and sweeping views.
9.2 out of 10, Wonderful, (16)
"Thanks, Etienne"
Large independent villa with pool: privacy, absolute quiet and sweeping views.
Outdoor dining
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
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Fridge, microwave, oven, stovetop
Vintage Villa Vagnucci - Cortona
10.0 out of 10, Exceptional, (1)
"Have stayed in area before, but not Cortona. We were taken around the property by Nonna and her grandson. A great team. They bogg live on siteNonna was attentive but not intrusive, and always left us tomatoes and basil from her garden, but spoke no english - more of a comment about us than her as it would have been great to talk to her more fully. A lovely lady. Stefano was great as translator, go to guy for info - taxi firms, air con specialists, bar to watch womens footy final! Etc A great...
Vintage Villa Vagnucci - Cortona
Indoor pool, outdoor pool
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
10.0 out of 10, Exceptional, (8)
"We were greeted upon arrival by Rafaello, our host, who was very helpful in getting us situated for our 5 night stay. The house is lovely, surrounded by the olive trees. The pool is pristine because Raffi comes to clean it every day. We did laundry in the unique washer and hung out the clothes on the drying rack that was provided. The views of the Tuscan countryside are lovely. Central location makes it easy to visit other Tuscan towns like Cortona, Siena, Montepulciano. I would recommend this...
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
Outdoor dining
Charming small villa near Cortona,garden,olive grove.A/C.Fiber Wifi -LA COLONICA
10.0 out of 10, Exceptional, (132)
"La Colonica is large and beautifully furnished - we only used one, but there are 2 large double bedrooms with showers. The hosts are very friendly, and David is English, so no communication problems. We were free to roam about the grounds - there is an olive grove attatched. There is an enormous, friendly dog who leaves white hairs all over you! The only drawback is that in the village (very picturesque) there are only 2 places to eat - 1 pizzeria and 1 restaurant. Apart from that the place is...
Charming small villa near Cortona,garden,olive grove.A/C.Fiber Wifi -LA COLONICA
Pool
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, (45)
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
Property grounds
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Pool
Belvilla by OYO Sparsa Girasole
10.0 out of 10, Exceptional, (1)
Belvilla by OYO Sparsa Girasole
Pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, (39)
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Fridge, microwave, oven, stovetop
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
9.8 out of 10, Exceptional, (40)
"We had a fantastic week in this lovely villa. It really does have everything you could possibly need - a real home from home. Lots of lovely spaces inside and out to enjoy. We loved sitting out in the evenings having dinner and we’re lucky to be there during the Perseus meteor shower and saw lots of shooting stars in the clear skys. We also ate out in the lovely town of Cortona - la buccia with beautifully presented food and a couple of more casual restaurants which were also excellent. The...
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
Exterior
Gorgeous Comfortable House with Garden & Pool - Its all yours.
10.0 out of 10, Exceptional, (15)
"We loved our stay at “Villa Rosa”. The owner was very informative and provided all the detail and recommendations we would ever need. Alex the property manager was there to greet us to show us around and later provided further answers. The Villa is very comfortable with all the amenities you could possibly need. Great Wi-fi too. We enjoyed particularly the pool area which is very private and secluded with great views over the rolling hills. My husband is a keen wildlife enthusiast, so he was...
Gorgeous Comfortable House with Garden & Pool - Its all yours.
Pool
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
7.4 out of 10, Good, (3)
"Un luogo che ha lasciato tutti noi (sia adulti che bambini) a bocca aperta: un paradiso terrestre! Per chi ama la natura, vuole staccare dalla caotica vita quotidiana e godere del tempo con i propri cari , questo è il posto che offre tutto ciò e di più! Non conoscendo bene la zona siamo arrivati un po’ impreparati ma tutto si è risolto con un viaggio al supermercato vicino Cortona! *essendo immersi nella natura c’è’ da far conto di insetti e possibili cervi e cinghiali, che rendono questo posto...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
Outdoor dining
Belvilla by OYO Bellosguardo
Belvilla by OYO Bellosguardo
Don't see what you're looking for?
See all available properties in Cortona
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.

Other types of properties in Cortona you may be interested in

Sauna, hot tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (166)
"Excellent experience!!! Very attentive staff in ALL areas. Room was beautiful!! Breakfast was outstanding!!! Spa space was amazing!!!! A few tight corners but well worth the drive!!!! Love, love, loved the stay! "
The price is HK$2,531
per night
22 May - 23 May
Monastero di Cortona Hotel & Spa
Courtyard
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, (174)
"Absolutely amazing"
The price is HK$3,943
per night
16 Jun - 17 Jun
Villa di Piazzano - Small Luxury Hotel of the World
Outdoor pool, pool umbrellas
Borgo Il Melone
4.0 star property
8.8 out of 10, Excellent, (236)
"Beautiful oasis surrounded by olive groves and Cyprus’s. Great staff in lobby and breakfast service- grazie Filipo and Micheal. Very clean spacious rooms with great shower. "
The price is HK$667
per night
17 May - 18 May
Borgo Il Melone
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.

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday apartments in Cortona using one of the methods below:

  • View our selection of featured holiday rentals in Cortona
  • Use the map to find apartments and other holiday homes in the Cortona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cortona while they last

Look no further and take a look at our great range of rental properties in Cortona!

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?

Podere Casorbica with free parking, large garden, swimming pool.: This highly rated holiday home rental in Cortona is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 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 balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Cortona is Nice house in the country of Cortona..

How many holiday rentals are there in Cortona?

With 275 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?

Enjoy the outdoors at Lake Trasimeno and Val di Chiana, or simply take in cultural attractions like Signorelli Theatre and Museum of the Etruscan Academy. While here, Piazza della Repubblica and Cathedral of Cortona 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.

Recent reviews of Cortona properties
Expedia verified reviews

Villa Borgo San Pietro

Villa Borgo San Pietro

5/5 Excellent
"Great hotel"
A verified traveller stayed at Villa Borgo San Pietro
Posted 4 days ago
Villa Borgo San Pietro