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Vacation rentals in Cortona

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Top-rated vacation rentals in Cortona

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Top guest favorite
A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.
Apartment in Cortona
4.99 out of 5 average rating, 172 reviews

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.

Top guest favorite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Condo in Cortona
4.98 out of 5 average rating, 195 reviews

Chicca: luminosa e panoramica nel centro storico

Luminoso, delizioso e accogliente appartamento situato proprio nel cuore del centro storico di Cortona con un panorama indimenticabile: il palazzo comunale da una parte ed il lago Trasimeno e la Valdichiana dall'altra. L'appartamento è stato recentemente ristrutturato ed è composto da una sala con divano letto, una piccola cucina, una camera matrimoniale e due bagni. Nell'appartamento è disponibile WiFi, riscaldamento ed aria condizionata, lavatrice, forno, microonde, asciugacapelli e piastra.

Top guest favorite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 127 reviews

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

Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 204 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite
A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.
Apartment in Cortona
4.97 out of 5 average rating, 180 reviews

CasaNella: luminosa, centrale e panoramica

Accogliente, elegante e delizioso appartamento nel centro di Cortona, con un panorama incantevole che spazia dal Lago Trasimeno alla Valdichiana. Accuratamente arredato, è il luogo ideale per trascorrere qualche giorno in questa meravigliosa cittadina. A due passi dalla strada principale, ma in una posizione silenziosa e panoramica. Parcheggio gratuito a breve distanza. Dotato di riscaldamento ed aria condizionata. Disponibile WiFi ad alta velocità. Ottimo per smartworking.

Guest favorite
A stone archway leads into a historic entrance, flanked by rugged walls covered with greenery. The pathway, lined with a metal railing, guides visitors through a tranquil setting enhanced by the natural surroundings.
Vacation home in Cortona
4.94 out of 5 average rating, 282 reviews

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.

Top guest favorite
A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.
Home in Prato
4.99 out of 5 average rating, 130 reviews

Tofanello Turquoise Luxury with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Top guest favorite
The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.
Home in Cortona
4.94 out of 5 average rating, 210 reviews

Casa del Passerino

Appartamento inserito all'interno di un palazzo storico di Cortona, collocabile nel 1500, con vista sulla piazza principale della città... La nostra struttura, pur condannando la guerra, si dissocia da tutti i comportamenti razzisti verso la popolazione russa e bielorussa. A Casa del Passerino le persone di queste nazionalità sono ben accette e saranno considerate alla stregua di tutte le altre. Vi aspettiamo in Toscana!

Top guest favorite
A small round table is set on a balcony, accompanied by two white chairs. A bottle of wine and two glasses are positioned on the table. The railing features decorative ironwork, framing a panoramic view over the terracotta rooftops and the valley below.
Apartment in Cortona
4.97 out of 5 average rating, 169 reviews

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"

Top guest favorite
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Apartment in Cortona
4.96 out of 5 average rating, 398 reviews

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

Top guest favorite
A sleeping area features a spacious bed with grey linens, positioned against a rustic stone wall. Natural light floods in through a window leading to a small balcony. A bedside lamp and a wooden table add warmth to the ambiance.
Apartment in Cortona
4.97 out of 5 average rating, 144 reviews

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.

Top guest favorite
A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.
Apartment in Cortona
4.96 out of 5 average rating, 177 reviews

Casa Le Contesse

È un piccolo appartamento, porzione della casa colonica dove vivo. È situato a piano terra, con accesso indipendente, in collina, in mezzo agli olivi, ad un km da Cortona. C'è possibilità di parcheggio, accesso privato, usufruire del giardino "superpanoramico''

Popular amenities for Cortona vacation rentals

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.

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