
Holiday rentals in Cortona
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Top-rated holiday rentals in Cortona
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Casa Lucy
Casa situata sulla collina cortonese, completamente ristrutturata, costituita da 3 camere matrimoniali, 2 bagni e openspace cucina e sala da pranzo. Si trova a 5 minuti dal centro storico di Cortona e in ottima posizione per raggiungere le più belle e caratteristiche località della Toscana e Umbria come Pienza, Montepulciano, Castiglione del Lago fino a città culle dell'arte come Firenze, Arezzo,Siena e Perugia. Obbligatoria tassa di soggiorno da pagare in loco (2,50 euro a persona per 4 giorni)

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.

Chicca: centro storico di Cortona
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.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

LA PICCOLA TERRAZZA
La piccola terrazza si trova nel centro storico di Cortona. Cortona è un piccolissimo paese della toscana vicinissimo alla splendida Firenze alla suggestiva Siena; alle bellezze del lago trasimeno . La piccola terrazza vi offre un appartamento all'interno di un palazzo storico composto da ingresso camera matrimoniale; camera con 2 lettini singoli cucina attrezzata e sala pranzo; bagno con doccia; e la splendida terrazza vista lago per poter sorseggiare un buonissimo vino a fine serata
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.

Casa Clara Cortona Cin IT051017c28a6h9glv
Beautiful two-room apartment inside the 1700s building, located in the heart of Cortona's historic center in front of the Signorelli Theater and Piazza Signorelli, 100 meters from Piazza della Repubblica. Harmonious and sober furnishings maintain the classic style of Tuscan houses with exposed beams and terracotta floors. Equipped kitchen. It's present - combustible gas detector - carbon monoxide detector - Fire extinguisher CIN IT051017C28A6H9GLV

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!

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

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"

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

Luxury - VISTA LAGO Trasimeno - Passignano - AC

Tuscan Casale near Cortona

Charming apartment with small gardens, pool access

La cantina di Arianna

Live Like a Local & Private Concierge Service

Casa Dina, appartamento centro storico Cortona

Casa Nobile

Agriturismo fringuello - Sofora
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
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cascate del Mulino
- Eremo Di Camaldoli
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Boboli's Garden
- Basilica of St Francis
- Avignonesi Winery Fattoria Le Capezzine
- Stadio Artemio Franchi
- Basilica of Santa Croce
- Great Synagogue of Florence
- Teatro Tuscanyhall
- Furlo Gorge Nature Reserve
- Teatro Verdi
- Palazzo Pubblico
- Mount Subasio
- Santa Maria della Scala
- Ugolino Golf Club
- Rocca Maggiore
- Castello di Verrazzano




