
Holiday houses in Cortona
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Cortona
Guests agree: these stays are highly rated for location, cleanliness and more.

Cortona’s Rooftop Nest
L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

THE LITTLE TERRACE
The small terrace is located in the historic center of Cortona. Cortona is a very small town in Tuscany very close to beautiful Florence, charming Siena, and the beauty of Lake Trasimeno. La Piccola Terrazza offers an apartment inside a historic building consisting of an entrance, double bedroom; bedroom with 2 single beds, equipped kitchen and dining room; bathroom with shower; and the beautiful terrace overlooking the lake to be able to sip a delicious wine at the end of the evening

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Chicca: bright and panoramic in the historic center
Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

La casina sulle Mura with garden
La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.
CasaNella: bright, central and panoramic
Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

Casa del Passerino
Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

I Terrazzini apt.1
In one of the most beautiful old buildings of the hystorical center, completely refurbished very sunny and scenic: a balcony with a spectacular view over Cortona roofs,Valdichiana, Trasimeno Lake and mountains far away. Living,attic,dinig,kitchen,bathroom,two bedrooms. Just few steps down the street and you are in Ruga Piana or Signorelli Square "movida"

Cortona Shabby Chic House - independent & balcony-
Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

Civetta golosa, Charming two-room apartment in the historic center
Cozy and practical two-room apartment on the second floor of a historic building, with an independent entrance and recently renovated. It is equipped with everything even for long stays. It has a comfortable double bedroom, bathroom and kitchen space. View of the city. Just 150 meters from the free parking lot in Piazzale del Mercato.

Signorelli
Come and enjoy our large and bright apartment in Tuscany charming and historical Cortona! You'll enjoy your own cozy and private lodging with a charming atmosphere, stone floors and artistic decor. You will be close to world class views of Cortona' valley a and lake.
Popular amenities for Cortona holiday rentals
Other great holiday rentals in Cortona

Casale La Cedrina (Il Melograno)

Il Sasso Apartment

Charming Apartment with Small Gardens, Pool Access

Via della Stella Farmhouse | Casa le Rose

La Terrazza Cortonese in town center with terrace

Town Center Apartment sleep 2, charming and cozy

Beautifully restored villa with private pool

Casa Vinalia: Etruscan paradise
Frequently Asked Questions
What are the best places to stay in Cortona?
Cortona has stays in the historic center, offering proximity to restaurants, main squares, and cultural sites, while rural homes around the town provide peaceful surroundings and countryside views. Both areas are frequently suggested.
What are the best things to do in Cortona with kids?
Visit the Etruscan Museum for interactive exhibits, explore the public gardens, and join family friendly cooking classes or outdoor activities. Many families enjoy sampling gelato in the town square.
What are some of the best things to do in Cortona?
Wander Cortona's hillside streets, explore the historic center, and visit museums highlighting Etruscan history. Many guests enjoy local art galleries, vibrant cafes, and panoramic viewpoints overlooking the valley.
How is the weather in Cortona?
Cortona experiences cool winters around 33–50°F (0–10°C) with occasional rain, and warm, dry summers between 60–89°F (15–32°C). Spring and autumn have moderate temperatures with increased rainfall.
When is the best time to visit Cortona?
Late spring and early fall are often recommended for visiting Cortona, with mild temperatures around 66–78°F (19–26°C) and blooming landscapes. These seasons tend to feature cultural events and local festivals.
What are the best places to visit in Cortona?
The MAEC Museum, Piazza della Repubblica, and the Church of Santa Margherita are frequently suggested; these sites showcase Cortona's historic depth and cultural heritage. Scenic overlooks around town offer striking valley views.
What are some hiking trails in Cortona?
Cortona has hillside trails that pass through olive groves, pine woods, and scenic lookout spots near its ancient city walls. Walking paths around the town are often suggested for glimpses of valley views and historic architecture.
What are some family activities we can do in Cortona?
Families can explore public parks, join guided walking tours, and try hands-on crafts or cooking experiences inspired by local traditions. Seasonal outdoor concerts and cultural celebrations are frequently enjoyed together.
What are some of the best day trip ideas from Cortona?
Explore neighboring Tuscan towns known for medieval architecture, wineries, and artisan shops, or visit local countryside estates. Lake Trasimeno and the surrounding villages are frequently suggested for day outings.
Are there any pet friendly accommodations available in Cortona?
Many stays in and around Cortona welcome pets, making it easy to explore the historic streets and nearby parks with your animal companion. Be sure to check each listing's pet policy before booking.
What are some local tips for visiting Cortona?
Start early to enjoy quieter streets and markets, and chat with local artisans for insight into traditional crafts. Light layers are helpful in changing weather, and many spots accept cash or cards.
What is Cortona known for?
Cortona is known for its Etruscan history, medieval architecture, and local Tuscan cuisine. The town’s scenic setting and cultural traditions often attract guests looking to experience authentic Italian life.
What are the best hidden gems to explore in Cortona?
Discover tucked-away alleys with artisan workshops, frescoed chapels, and small local eateries serving traditional dishes. Around Cortona, ancient city walls and quiet green spaces feel less frequented but rewarding.
What are the best foods to try in Cortona?
Try local specialties like wild boar stew, handmade pici pasta, and aged pecorino cheese, often served at traditional trattorias. Seasonal produce, olive oil, and regional wines are frequently highlighted in meals.
What should I bring for a trip to Cortona?
Comfortable walking shoes are useful for hilly cobbled streets, and a light jacket helps during cooler evenings. Bringing a reusable water bottle and sun protection is often suggested, especially in summer.
What is the nightlife in Cortona like?
Cortona’s nightlife leans toward intimate wine bars, outdoor cafes, and occasional live music in local venues. The atmosphere is relaxed, with options for enjoying regional wines or small plates.
What are the most popular events or festivals in Cortona?
Cortona has art and music festivals in the summer, food fairs celebrating Tuscan harvest traditions in autumn, and Holy Week processions that gather locals and visitors in the historic center. These events are frequently suggested ways to experience regional culture.
Are there family friendly vacation rentals in Cortona?
Cortona has a selection of family friendly vacation rentals, many with spacious layouts and access to gardens or kitchens. Families can find homes near the historic center or in quieter areas around town.
Destinations to explore
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Piazzale Michelangelo
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Boboli's Garden
- Eremo Di Camaldoli
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Teatro Tuscanyhall
- Basilica of Santa Croce
- Teatro Verdi
- Mount Subasio
- Palazzo Pubblico
- Furlo Gorge Nature Reserve
- Santa Maria della Scala
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Casa Barthel




