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Apartment vacation rentals in Cortona

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Popular amenities for Cortona apartment rentals

Weekly 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 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.
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!
Superhost
Apartment in Fratta-Santa Caterina

Charming Apartment Garden, Pool

ChrisRating, 5 stars2 weeks ago
Very well appointed, super quiet location and our host was very responsive. We would stay there again!
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 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.

Private apartment rentals

Top guest favorite
Apartment in Asciano
4.89 out of 5 average rating, 76 reviews

Farmhouse apartment with pool

JulieRating, 5 stars2 weeks ago
The apartment is located in an enchanting place! The scenery is breathtaking. The kitchen is well equipped, we cooked good food. The sunsets are beautiful and the pool is very convenient for cooling off after a day of sightseeing. A special thank you to Deb, the neighbor who welcomed and guided us throughout our stay. Thanks to her recommendations, we discovered a vineyard: Ciarliana, where Sara gave us a tasting that exceeded our expectations. We're totally in love with 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 Cortona
4.86 out of 5 average rating, 95 reviews

Cortona studio apartment for vacation

IvanRating, 5 stars1 week ago
Rosario and Sebastiana's place was nice, clean and functional. We had a good time even staying with a child. The kitchen is well-stocked with all the utensils, as is the bathroom. The apartment is very cool, even though we stayed in June. The location is great, with free parking nearby and very close to the main square. The owners are two really nice and helpful people.
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!
Top guest favorite
Apartment in Siena
4.97 out of 5 average rating, 32 reviews

Palazzo del Papa Standard Suites

TravisRating, 5 stars1 month ago
AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.
Top guest favorite
Apartment in Montepulciano
4.95 out of 5 average rating, 86 reviews

Casa Crociani - Amazing Pool & Free Parking

CathyRating, 5 stars4 days ago
We loved our stay at Marco’s. The cottage, pool, location were wonderful and the views amazing. Perfect way to end our vacation. Very thoughtful with snacks and drinks provided. .
Guest favorite
Apartment in Montefollonico
4.87 out of 5 average rating, 61 reviews

The Tuscan Belvedere - Amazing Terrace in Tuscany

LioraRating, 5 stars1 week ago
Spacious place in an amazing quiet old medieval town. Spectacular view off the little balcony. Highly recommend!

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 Montepulciano
4.92 out of 5 average rating, 142 reviews

Charming House in Montepulciano

KirstenRating, 5 stars3 months ago
Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!
Top guest favorite
Apartment in Siena
4.98 out of 5 average rating, 104 reviews

Domus Nannini - L'Arco di Matteotti Spa

LeratoRating, 5 stars1 week ago
Excellent location and comfortable stay. Thanks to Alessandro for assisting me with the check-in.
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!

Destinations to explore

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