
Vacation rentals in Cortona
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Top-rated vacation rentals in Cortona
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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: 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.

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
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.

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.

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

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!

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,Grazioso bilocale in centro storico
Accogliente e pratico bilocale al secondo piano di edificio storico, con ingresso indipendente ed appena ristrutturato. È fornito di tutto anche per soggiorni lunghi. Dispone di comoda camera matrimoniale, bagno e spazio cucina. Vista sulla città. A solo 150 metri dal parcheggio gratuito di Piazzale del mercato.

Baldelli | Apartment in the city's main square
This apartment, named Baldelli, is located in Piazza della Repubblica.From one side of the house you can see the city hall building and from the other one there is a great Val di Chiana view. The apartment has a double bedroom, a living room with desk and a sofa, a bathroom with shower, a kitchen full equipped.

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 vacation rentals
House rentals in Cortona

Interno Italiano

Casolare immerso nella natura

Da nonna Ornella - nido in Val d’Orcia

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

La Perla del Lago Casa vacanze al Lago Trasimeno

Raffaella's House nel Chianti

PIAZZETTA S.BARTOLOMEO

Jenny's Barn
Boutique hotels in Cortona

Boutique Hotel L’imperatrice

Romantico Borgo Medievale con piscina

Boutique room - Torre - Di Colle in Colle

Clarissa - Suite Classic

Villa Rigacci boutique hotel in Valdarno area

Nice double room in a charming B&B

Camera in Residenza D’epoca, Abbazia, agriturismo

Agriturismo Merigge Wellness & Spa Montepulciano
Other great vacation rentals in Cortona

Stunning Tuscan Villa & Panoramic Infinity Pool

La Vista

Relaxing-unspoiled country place Il Monte...

Terrazza Silena, centro storico con vista Cortona!

Casa AlMa: aria condizionata e terrazza privata

La Terrazza sulla Valle

Apt. Elena- Tenuta Villa Augusto

Breathtaking Views + Terrace/Central yet Quiet
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
- Piazzale Michelangelo
- Lake Trasimeno
- Lake Bolsena
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Stadio Artemio Franchi
- Tenuta Le Velette
- Basilica of St Francis
- Castiglion del Bosco Winery
- Basilica of Santa Croce
- Teatro Tuscanyhall
- Teatro Verdi
- Furlo Gorge Nature Reserve
- Mount Subasio
- Cantina Colle Ciocco
- Santa Maria della Scala
- Palazzo Pubblico
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Podere Il Cocco




