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Holiday rentals in Cortona

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Top-rated holiday rentals in Cortona

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Flat in Cortona
4.99 out of 5 average rating, 177 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 favourite
Home in Cortona
5 out of 5 average rating, 20 reviews

Breathtaking views: Historic House w/Terrace & BBQ

Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, stillness, and the atmosphere of an authentic home.

Top guest favourite
A spacious living area is presented with a patterned sofa and a glass coffee table. Warm wood beams accent the ceiling, and a soft rug covers the floor. Light flows through the room, creating a comfortable and inviting space with access to other areas of the apartment.
Flat in Cortona
4.96 out of 5 average rating, 129 reviews

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

Top guest favourite
A light-filled living room features a cozy, L-shaped couch adorned with decorative cushions. A small round table sits between two green glass vases, while glass doors lead to an outdoor area. The wooden ceiling and neutral tones create a serene ambiance.
Home in Cortona
5 out of 5 average rating, 73 reviews

Casa Primo Stylish-townhouse w/ patio & jetted tub

Casa Primo è situata nel cuore del centro storico di Cortona. La struttura gode della posizione ideale per i viaggiatori che vogliono assaporare e lasciarsi trasportare dai colori e dai sapori di Cortona, piccola meraviglia etrusca, con i suoi vicoli, i suoi panorami, le sue botteghe artigiane, i suoi ristoranti e la sua arte. Casa Primo, con il suo giardino segreto, vi accoglierà in un’atmosfera magica in perfetto equilibrio tra passato e futuro, dando vita a uno spazio unico.

Top guest favourite
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.
Apartment in Cortona
4.99 out of 5 average rating, 210 reviews

Chicca: Cortona's 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.

Guest favourite
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.
Holiday home in Cortona
4.94 out of 5 average rating, 287 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 favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5 out of 5 average rating, 150 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 184 reviews

CasaNella: central, bright, and with a view

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.

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 413 reviews

Cortona Shabby Chic House - independent & balcony-

Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. 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

Guest favourite
A private garden space is shown, featuring a gravel surface and bordered by potted plants. A small green table is paired with a single chair, creating a cozy area for relaxation. The surrounding stone walls and buildings provide a historic context to the setting.
Flat in Cortona
5 out of 5 average rating, 20 reviews

Casa Caterina

Casa Caterina develops on 3 floors and it has spacious and bright rooms (total 100 sqm) and can accommodate up to a maximum of 6 guests (2 double bedrooms and 1 double sofa bed subject to an additional fee). A small yet lovely private garden with table and chairs. You access the building by 2 private entrances, one directly from the garden and the other from a main door with a comfortable stone staircase that ...

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 177 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 favourite
A rustic stone house is surrounded by lush greenery, featuring wooden shutters and a tiled roof. A shaded outdoor dining area is visible, complemented by potted plants. The serene garden setting invites relaxation and enjoyment of the natural landscape.
Home in Torreone
4.97 out of 5 average rating, 110 reviews

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.

Popular amenities for Cortona holiday 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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