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Apartment holiday rentals in Cortona

Find and book unique apartments on Airbnb

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Popular amenities for Cortona apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in Camucia
4.95 out of 5 average rating, 57 reviews

Il Sasso Apartment

AlisonRating, 5 stars1 month ago
For a stay in Camucia, this is the place. No need to look further. It's in beautiful surroundings, the apartment is brlliantly new and clean. It contains everything you need and if you want to cook, the kitchen is well-equipped. There is a double bed and a bed settee in the lounge. The balcony is large and perfect for sitting outside near the trees. Christina communicates brilliantly. She came to pick me up when my friend didn't arrive and her husband immediately fixed the wifi after a storm. This is a perfect Airbnb and I would have no hesitation in staying there again.
Superhost
Flat in Cortona
4.79 out of 5 average rating, 39 reviews

Casa Samuela

MeganRating, 5 stars1 month ago
Great stay! Super central and walkable but also quiet and peaceful. Check in instructions were super clear and they were super flexible and had the place ready for early check in even though I booked same day. The staff in the check in office was friendly and helpful and showed me to the place so it was easy to find.
Guest favourite
Flat in Siena
4.92 out of 5 average rating, 119 reviews

[Piazza del Campo] Elegant loft with terrace

PeterRating, 5 stars2 weeks ago
Wow! What a beautiful place to stay! The roof terrace was amazing with beautiful views across rooftops to the Tuscan countryside. The centre of Siena with its Piazza del Campo is only a few minutes stroll away and the Duomo not much further. There are plenty of restaurants all around and a decent supermarket 3 minutes walk away. The apartment is well equipped with everything we needed for our stay. We would highly recommend!
Top guest favourite
Flat in Centro Storico
5 out of 5 average rating, 269 reviews

Piazzale Michelangelo among the olive trees

ElliotRating, 5 stars1 week ago
Beautiful house, a short walk from the Piazzale Michelangelo for a stunning viewpoint. Francesca is an amazing host, very friendly and dedicated to making our stay enjoyable. The house was clean and well stocked with essentials, and the air conditioning worked very well. She gave us lots of recommendations and information on the area too. The area itself is incredibly peaceful and you can enjoy a quiet evening in the beautiful garden. We would come back again!
Top guest favourite
Flat in Barberino Val d'Elsa
4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

MarkusRating, 5 stars1 week ago
We have now been to Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can switch off perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!
Top guest favourite
Flat in Montepulciano
4.97 out of 5 average rating, 349 reviews

A generous space between ancient and modern in the center of Montepulciano

PriceRating, 5 stars3 days ago
Look no further! We were sad to only get one night here. The location, ambiance, and host make this place worth every penny. Emanuela is the best host I’ve had on Airbnb. Book this — you won’t be disappointed.
Guest favourite
Flat in Assisi
4.96 out of 5 average rating, 187 reviews

Apartment in Piazza del Comune

AmyRating, 5 stars5 days ago
Very nice place, central location, beautiful decor, and Andrea is so helpful!
Guest favourite
Flat in Scrofiano
5 out of 5 average rating, 47 reviews

Charming apartment,balcony, beautiful view, A/C

MaureenRating, 5 stars3 weeks ago
We really enjoyed our stay at this really unique accommodation. It is located in a medieval village, high on a hill. The apartment is compact, but has everything you need. The view from the balcony is fantastic. Malgorzata was a great host and very responsive when we had questions. I would not hesitate to recommend this property.

Private apartment rentals

Guest favourite
Flat in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favourite
Flat in Castelnuovo Berardenga
4.88 out of 5 average rating, 25 reviews

Colle ai Lecci: Design Apartment in Tuscany

GülcanRating, 5 stars2 weeks ago
We had an unforgettable time here - the nature as well as the facility itself are beautiful, a bit rustic with a few renovations, about which Ana can tell a lot. You can spread out on the grounds, have enough privacy if desired and can watch the most beautiful sunsets. The pool between the olive trees is also fantastic. From here, we were able to visit some cities such as Florence and Siena, and here, too, Ana had great tips for suitable restaurants. We will be happy to come back!
Top guest favourite
Flat in Cortona
4.97 out of 5 average rating, 62 reviews

Terrazza Silena, historic center with Cortona view!

OliverRating, 5 stars2 weeks ago
Excellent location in the heart of cortona. Lovely balcony with excellent view but as mentioned lots of steps to make it up to the flat hut worth it if you are able! Very well equipped.
Top guest favourite
Flat in Cortona
4.96 out of 5 average rating, 28 reviews

La Terrazza sul Valle

RichRating, 5 stars1 month ago
The perfect home away from home in Cortona. Vanna was a delightful hostess. The city center was a convenient short walk up the hill on Via Guelfa to Piazza Republica, restaurants, bars, and shops. It is close to the bus stop. The apartment had a well stocked kitchen, washing machine and other conveniences that made the stay comfortable. There were plenty of linens and modern bathrooms. And “la terraza” overlooking the valley is a special asset.
Top guest favourite
Flat in Centro Storico
5 out of 5 average rating, 25 reviews

Loggia in the Santo Spirito district

MyaRating, 5 stars1 week ago
We had the most amazing stay at Sibilla's apartment! It is STUNNINGLY decorated and almost makes it feel like you are staying in the Medici Chapel itself. The apartment had everything we needed, and the plant room/ sunroom was glorious to enjoy in the mornings/returning after a day's exploring. We met both Niccolo and Sibilia and both were so friendly and helpful. The area surrounding the apartment is perfect, with central Florence being a 20 minute walk away, and the restaurants/shops/wine bars of Santo Spirito being literally on your doorstep. This is the most enjoyable Air BnB we have ever stayed in, and would come back in a heartbeat! Grazie mille!!
Top guest favourite
Flat in Pienza
5 out of 5 average rating, 33 reviews

Live Like a Local & Private Concierge Service

MarydithRating, 5 stars6 days ago
I can’t say enough about our hosts! They were communicative from start to finish and our experience would not have been the same without them. Our favorite part was doing the cooking class and having dinner with them and their family.
Top guest favourite
Flat in Cortona
4.88 out of 5 average rating, 34 reviews

Tina’s House

FabioRating, 5 stars2 weeks ago
Everything extremely perfect! Great apartment, 2 steps from the center. Very good!
Guest favourite
Flat in Montepulciano
4.91 out of 5 average rating, 75 reviews

Casa Evelina - Incredible View, Central Location

LisbethRating, 5 stars3 days ago
This is a great location in the heart of montepulciano. You walk out of the unit and onto the main street full of restaurants and shops. The house is spacious with three bedrooms all with comfortable beds. There were extra pillows and linens, which are always helpful. We had all the windows open due to warmer weather with a nice breeze at night. Despite being right on the street, we did not hear any evening noise throughout the night sleeping was peaceful. The views from the apartment are exquisite.

Apartment rentals with a hot tub

Guest favourite
Flat in Centro Storico
4.88 out of 5 average rating, 165 reviews

Love Honeymoon Jacuzzi Piazza Signoria View Ac WiF

MatthewRating, 5 stars2 weeks ago
Our stay at Luca’s place in Florence was wonderful. The location was extremely convenient with main attractions like the uffizi and galleria dell’academia just a short walk away. The apartment is also located in a very nice square that is lively and fun, but not noisy from the room. There are many restaurants and shops just down the stairs. The room itself was all that we could have wanted. The whirlpool tub was a very nice feature, the bed was conformable, and the atmosphere of the room was very cozy. If we return to Florence, we would love to stay at Luca’s place again!
Guest favourite
Flat in Perugia
4.96 out of 5 average rating, 316 reviews

A Cosy flat

KimonRating, 5 stars2 weeks ago
Had a super 8 night stay here. Paola, the host, is everything you can hope for from an Airbnb host. Super communicative, welcoming and helpful. Her and her husband helped me with a medical issue, which was so kind and appreciated. Wow! Just wow! The apartment is quiet and I slept good at night. It has every amenity that I needed. It is clean and in a safe location. They really put love and attention into this place and it shows. Highly recommended.
Guest favourite
Flat in Centro Storico
4.93 out of 5 average rating, 542 reviews

House of Delights - The Medici private leisure house

XavierRating, 5 stars2 weeks ago
Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.
Superhost
Flat in Centro Storico
4.8 out of 5 average rating, 708 reviews

.2 La Casa sui Tetti dell 'Oltrarno

CharlesRating, 5 stars1 month ago
Superb spot close to river. Bed is confortable. Yes, stairs could be a challenge for some only it is clearly stated. At the end of the day, it’s alright!
Top guest favourite
Flat in Siena
4.94 out of 5 average rating, 109 reviews

Domus Nannini - L'Angolo di Paradiso Spa (Spa)

DanyelleRating, 5 stars3 weeks ago
After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!
Top guest favourite
Flat in Centro Storico
4.98 out of 5 average rating, 268 reviews

[Ponte Vecchio] Prestige and unique view

VieriRating, 5 stars4 days ago
Excellent location and beautiful apartment. Easy to get in self-check in and good communication with the host. Great kitchen, stocked with all the hardware you need. Common area was comfortable for the 4 of us. The view is amazing. Balconies on the water with close up views of Ponte Vecchio. Definitely one of the best places we've stayed in a 20 day trip in several cities.
Guest favourite
Flat in Perugia
4.85 out of 5 average rating, 190 reviews

Blue University Apartment - Downtown

JoachimRating, 5 stars1 week ago
Great place, good location, with secure place for the car
Top guest favourite
Flat in Siena
4.91 out of 5 average rating, 129 reviews

Villa'Colombaiolo di Marciano', 28

HannahRating, 5 stars3 weeks ago
We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Cortona
  6. Flat rentals