Cortona Holiday Rentals

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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.

9.8 out of 10, Exceptional, (64)
"Property is perfect for the view and the loction"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Appartamento Loggetta
Apartment, 1 Bedroom | View from room

Appartamento Loggetta

Appartamento Loggetta
Podere Casorbica with free parking, large garden, swimming pool.
Exterior

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

9.4 out of 10, Exceptional, (13)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, 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, (62)
"This house and adjacent apartment was perfect for a larger group. The rooms are comfortable and well equipped. The property was lovely and has a spectacular pool. A few things to note. The house name is not a location on a map and if you use an app like Google then you must use the name on the wall outside the property. The hot water takes a very long time to get to the upper floor shower and it’s almost impossible to fill a hot bath. That’s to be expected in a house of this age and it’s well...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Casa Nobile - a noble apartment few steps from the main square
Interior

Casa Nobile - a noble apartment few steps from the main square

9.0 out of 10, Wonderful, (2)
"Overall a beautiful and well maintained apartment in a great location. The only thing stopping me from giving it 5 stars across the board is the fact it is on the 4th floor with no lift. We had large suitcases which made it a challenge. Otherwise, a charming apartment in Cortona. "
Casa Nobile - a noble apartment few steps from the main square
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)
"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
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
Cottage " I due Pini"
Outdoor dining

Cottage " I due Pini"

10.0 out of 10, Exceptional, (36)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Fratta Orchidee, Cortona, Italy
Fridge, oven, stovetop, dishwasher

Fratta Orchidee, Cortona, Italy

Fratta Orchidee, Cortona, Italy
Villa Primula - Holiday Rental in Cortona, Tuscany
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
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, (43)
"Villa Calcinaio was a beautiful place to spend our time while in Cortona. My goal was to get a slice of Tuscan life and this house gave me the opportunity to do just that. It was rustic but charming and updated ~20 years ago. Enrico was very responsive and even came to our rescue when we had trouble locating the house on the dark and rainy night when we arrived. I found the house stocked with all the basics and then some and I fell in love with the view of the beautiful dome from every...
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Villa Mulino - Completely renovated old mill in Tuscany
Outdoor spa tub

Villa Mulino - Completely renovated old mill in Tuscany

9.8 out of 10, Exceptional, (6)
"We enjoyed our stay very much. Everything is perfect. The "
Villa Mulino - Completely renovated old mill in Tuscany
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, (40)
"Fabulous location and property. We had a fantastic family holiday in the house. Great area to explore. Madeline was lovely. We will be back"
Beautiful villa with spectacular views in a rural location
Nice house in the country of Cortona.
Exterior

Nice house in the country of Cortona.

8.6 out of 10, Excellent, (11)
"The house was neatly kept and quiet. Cortana was visible on the hill. Marzi was friendly and helpful in meeting our needs The down side was a pot holed rural road to get here and cool living room temperatures the first few days as it took the masonry walls time to warm up in the cool March temperatures."
Nice house in the country of Cortona.
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Outdoor dining

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

9.8 out of 10, Exceptional, (55)
"H"
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Heritage Tuscan Farmhouse with private swimming pool
Pool

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (44)
"We had a very happy stay at this house in the country with our two friends. It is ideally located within an hour’s drive of interesting sites and historic towns. The place and its surroundings allowed us a restful and pleasant respite from our busier daytrips. The house was comfortable, beds were very good and the garden provided a peaceful setting with a choice of sitting and lounging areas. Louise was lovely, an excellent hostess who responded quickly to our questions and needs. "
Heritage Tuscan Farmhouse with private swimming pool
Belvilla by Oyo Villa Letizia
3 bedrooms, free Internet

Belvilla by Oyo Villa Letizia

8.0 out of 10, Very good, (8)
"We couldn’t have been happier with our stay! Our Villa had an old world charm that was just what we wanted while staying in Tuscany! The view was AMAZING! Our host was so responsive and gave us a private tour of his Cortona. We took advantage of the hot tub and the private bath that was set up with candles and champagne! Another recommendation would be to have dinner with Luka.( our host) in his home. The food was traditionally prepared and amazing. Overall an wonderful stay!!"
Belvilla by Oyo Villa Letizia
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Outdoor dining

Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool

10.0 out of 10, Exceptional, (46)
"This property is all it explains to be. The stay included myself, my husband, my daughters and their families. The property is spectacular, the rooms as beautiful as shown. The guesthouse was perfect for my daughter, her husband and 2 young children. The travel cots were perfect and opening the chest of toys brought so much joy to my 2 year old granddaughter. We utilized the kitchen and pizza oven and have such wonderful memories to hold. Our only disappointment was that the pool heater was not...
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
Pool

Beautifully converted farmhouse alone on a tuscan hillside with stunning views

8.6 out of 10, Excellent, (15)
"Having vacationed in this area for the last 20 years and lived here for four, rarely have we come across a restoration with the attention to detail and clearly a personal touch from someone passionate about this special place. A beautifully restored farmhouse interior with plenty of space and good size rooms all finished to a high standard. The living room especially is a comfortable and inviting escape when it’s too hot outside. The outside areas and furniture could do with some renewal to...
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
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, (10)
"We were a family group of 15 ranging in age from 20 to 92. We used the pool every day. Laughed at the clothes dryer because they have the same kind in Portugal where we vacationed. Many people walked into Camucia and enjoyed the restaurants grocery stores etc. Several of us have been to Italy before my first time in Assisi but we shared experiences with them. Staff was prompt to arespond to any problems. And a week of perfect weather makes it all the better"
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
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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Other types of properties in Cortona you may be interested in

Villa di Piazzano - Small Luxury Hotel of the World
Courtyard

Villa di Piazzano - Small Luxury Hotel of the World

5.0 star property
9.8 out of 10, Exceptional, (200)
"The Villa di Piazzano is stunning down to the smallest detail. The staff is attentive, pleasant and helpful. The food and wine at the onsite restaurant was some of the best we had on our 23-day trip across Italy. One of our favorite stays for sure!"
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa
Sauna, hot tub, steam room, massages

Monastero di Cortona Hotel & Spa

5.0 star property
10.0 out of 10, Exceptional, (203)
"Super friendly service from most of the staff and beautiful property, restaurant and bars were great too. "
Monastero di Cortona Hotel & Spa
Borgo Il Melone
Outdoor pool, pool umbrellas

Borgo Il Melone

4.0 star property
8.6 out of 10, Excellent, (277)
"We were initially uncertain about booking here due to some negative online comments; however, very happy we did! it would be difficult to pristinely maintain the property as it is historic and quite large, so if you’re looking for something with every modern amenity, this is not the stay for you. However, the property is a gorgeous setting and the buildings are quaint and charming. Our room was very spacious - a bit of noise transfer through the bathroom. Pool area is beautiful! Great breakfast...
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.

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. You can relax into your holiday with a balcony and a garden. 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 263 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 Signorelli Theatre and Museum of the Etruscan Academy, 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.