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Apartment vacation 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 favorite
Apartment 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.
Top guest favorite
Apartment 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 favorite
Apartment in Cortona
4.96 out of 5 average rating, 28 reviews

The Terrace on the Valley

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.
Superhost
Apartment 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.
Top guest favorite
Apartment in Pienza
5 out of 5 average rating, 33 reviews

Live Like a Local & Private Concierge Service

MarydithRating, 5 stars1 week 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 favorite
Apartment in Cortona
4.88 out of 5 average rating, 34 reviews

Tina’s House

FabioRating, 5 stars3 weeks ago
Everything extremely perfect! Great apartment, just a short walk from the center. Very good!
Guest favorite
Apartment in Siena
4.86 out of 5 average rating, 43 reviews

Fine house with altana and panoramic terrace

JohnRating, 5 stars10 months ago
This was one of the most amazing Airbnb properties I've ever had the pleasure in experiencing. It's a penthouse apartment overlooking the tiled rooftops of Siena, with a view straight across to the famous church tower. Taking your morning coffee here with the pigeons is one of the most serene things you could imagine. Pure Italy. There's also a rooftop garden we could pull fresh cherry tomatoes and basil from for our cooking. It's located literally a 3-minute walk from the main piazza, and in the middle of all Sienna's shopping, walking, and dining attractions. Nicoletta was patient with our travel schedule, and met us on the later side of our check-in without a problem.
Superhost
Apartment in Cortona
4.85 out of 5 average rating, 48 reviews

Apartment Il Loggiato

IsaakRating, 5 stars4 weeks ago
Perfect place to stay in town. The apartment is close to all the amenities in town, while keeping a sense of privacy, providing a perfect balance. We had a great time in Cortona!

Private apartment rentals

Guest favorite
Apartment 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!
Top guest favorite
Apartment in San Quirico d'Orcia
5 out of 5 average rating, 80 reviews

Antica Loggia - Apartment with view

LynnRating, 5 stars1 week ago
Claudia is an excellent host! She met us at check in and greeted us with hugs. She had a bottle of wine and plenty of coffee pods for us to enjoy! Her place was super clean and charming! She truly has thought of every detail! The air conditioning was lovely and she even has a nice fan, which we used on the balcony. We loved the covered balcony and spent most of our time there. So beautiful! After having spent many days at another Airbnb without a covered balcony, we really appreciated the shade that offered such a nice view. The kitchen had everything we needed as well. She also had several types of milks, juices and a breakfast cereal and bread available! The town was mostly quiet and relaxed with a few shops and restaurants. The location was perfect for day trips. We enjoyed a full day in Sienna. Thank you, Claudia, for your fabulous hospitality!
Guest favorite
Apartment in Castelnuovo Berardenga
4.88 out of 5 average rating, 26 reviews

Colle ai Lecci: Design Apartment in Tuscany

JamesRating, 5 stars2 weeks ago
Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!
Guest favorite
Apartment in Roccastrada
5 out of 5 average rating, 15 reviews

Apartment in a wine estate

Steven JohnRating, 5 stars1 month ago
We had a wonderful 4 day stay, thank you for your hospitality, to all the staff and family. First class, recommended restaurants plus made reservations for us, which were needed, and recommended sites to visit. Rooms were spacious and clean, grounds were beautiful, wine tasting and Stephan’s knowledge of wine making made the tour. We also had breakfast every morning, and one evening had a dinner, recommended. A beautiful couple, so glad we meet them. Hopefully we will be back again.
Guest favorite
Apartment in Monteroni d'Arbia
4.95 out of 5 average rating, 65 reviews

San Giovanni in Poggio, Twilight app. 60 sqm

ŁukaszRating, 5 stars1 month ago
Marvelous place, Sara is very friendly and helpful host. Can’t wait to visit this place again.
Top guest favorite
Apartment in Castiglion Fiorentino
5 out of 5 average rating, 57 reviews

Medieval Delight! Rustic Beams w/Modern Amenities

LoriRating, 5 stars4 months ago
Amanda's apartment provided a warm, comfortable, and well-appointed home for a month in Castiglion Fiorentino. The laundry room, large kitchen, and private outdoor space were the perfect amenities for an extended stay for a couple. Part way through our trip, we had friends rent the attached apartment and we opened the adjoining doors so we could play cards in front of the fire in the evenings. Amanda arranged occasional cleanings during our stay, as well as organizing cars to/from the train station on our arrival and departure. This is a beautiful, safe, and walkable hill town with fantastic restaurants, museums, churches, and shops that were open even in the off season. The people, town, and food were warm and wonderful. We began Italian language lessons while there and became regulars at the Cafè Le Logge with its incredible view. We took regular daytrips by train to Arezzo or Florence, and by bus or car to Cortona and Chiusi. We could have stayed a month longer! Amanda was amazing!
Guest favorite
Apartment in Sant'Arcangelo
4.76 out of 5 average rating, 83 reviews

Trasimeno Lake - "The Convent"

ElkeRating, 5 stars5 days ago
Nicola and Stefano's place was a real highlight. The apartment, building and surrounds are stunning and the pool was such a lovely retreat at the end of the day exploring. We were met at the bottom of the hill and shown how to access the property and everything is as is shown in the photos. The location is close to so many beautiful towns, restaurants and other activities you could easily stay for much longer. The hosts were very responsive and easy to communicate with and provided recommendations for food and activities when we asked. The apartment had everything needed for our little family to cook and live for a week, all the rooms have fans for the heat. We absolutely loved it. Thank you for having us.
Top guest favorite
Apartment in Montepulciano
5 out of 5 average rating, 59 reviews

Luxury Attic in Tuscany+Incredible view and A/C

EugenioRating, 5 stars3 weeks ago
Staying at this apartment was truly magical. Every time I looked out the window or stepped onto the balcony, I was left in awe. The views were absolutely breathtaking, and the town of Montepulciano was every bit as beautiful—charming, historic, and full of character. Leaving was the hardest part, and I’m already counting down the days until I can return. From the incredible local restaurants to the stunning wineries nestled in the Tuscan hills, every moment felt like a dream. Photos simply can’t capture the beauty—you have to experience it for yourself.

Apartment rentals with a hot tub

Superhost
Apartment in Cortona
4.96 out of 5 average rating, 53 reviews

Il Vicolino, sauna and hot tub

SaraRating, 5 stars1 month ago
Small treasure in the alleys of the historic center of Cortona. Well-kept and clean environment, true to description! A note of merit to the host who provided specific directions to get to free parking near the property, avoiding the historic center with paid areas and above all for the availability to accommodate some small requests from us guests! Recommended!
Superhost
Apartment in San Giovanni d'Asso
5 out of 5 average rating, 20 reviews

Podere Ferranino #Cimabue Townhouse

CoreyRating, 5 stars2 weeks ago
Amazin relaxation! Great space, gorgeous view, and they even have an electric charging station!
Guest favorite
Apartment in Montevarchi
4.91 out of 5 average rating, 104 reviews

Apartment with garden in the heart of Tuscany

Mary BethRating, 5 stars7 months ago
Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!
Guest favorite
Apartment 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.
Top guest favorite
Apartment in Montone
4.97 out of 5 average rating, 32 reviews

Annex in the Cardaneto Castle

AgnesRating, 5 stars4 days ago
Our stay was really magical! Of course, the ambience is wonderful, it is very quiet there and it takes about 20 minutes to walk to the restaurants in Montone, but we wanted it exactly like that! The pool, the view - really everything was fantastic! And our great hosts are simply outstanding! They were always there to help, gave us great recommendations for the area and even organized and translated a truffle hike for us! We are incredibly grateful to have been able to stay in this gem and get to know this wonderful and loving family! Thanks for everything 😊
Top guest favorite
Apartment 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!
Superhost
Apartment in Siena
4.91 out of 5 average rating, 132 reviews

Penthouse in Siena near Piazza del Campo and Palio

ElizabethRating, 5 stars1 month ago
We had a fabulous stay here, there was more than enough rooms and space to relax after a day of sightseeing. The view from the living room is gorgeous, the rooms are all charmingly decorated and it had all the amenities we needed: separate beds for 4 adults, large enough showers, laundry and kitchen as well as cosy living room. Federico was very friendly, responsive and made us feel at home immediately. Highly recommend!
Guest favorite
Apartment in Perugia
4.85 out of 5 average rating, 191 reviews

Blue University Apartment - Downtown

PaulaRating, 5 stars4 days ago
Fabrizio was very quick to communicate and kind, and gave great restaurant recommendations. The apartment was very clean and is very well located

Destinations to explore

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