
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.

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.

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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance 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

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.

I Tramonti di Eramo, Montepulciano city center.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.
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.

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

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!

Dimora dell'Erbe - Rooftop Apartment
The apartment has two independent double bedrooms with private bathroom (Nepitella and Timo), a large bright kitchen with living room and finally exclusive access to the beautiful terraces that overlook the roofs of Montepulciano. The modern and functional kitchen offers an induction hob, dishwasher fridge and a service for 6 people. Independent air conditioning and heating and wi-fi.

Baldelli | Apartment in the city's main square
This apartment, named Baldelli, is located in Piazza della Repubblica and it’s a the third floor of an historic building without elevator. The apartment has a double bedroom, a living room with desk and a sofa, a bathroom with shower, a kitchen full equipped. 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.

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"
Popular amenities for Cortona vacation rentals
Boutique hotels in Cortona

Romantic Medieval Village with pool

Boutique room - Tower - From Hill to Hill

Clarissa - Suite Classic

Villa Rigacci boutique hotel in Valdarno area

Romantic Living!

Antique Guest Room and Heated Pool

Room in Historical Residence, Abbey, farmhouse

Modern Day Hermitage
Other great vacation rentals in Cortona

Romantic cottage in Tuscany with pool and garden

Villa Le Murate

The window on the Theater

Farmhouse in Novole ,Cortona Tuscany

Arianna's winery

Country charm walking distance from Cortona centre

Elegant farmhouse overlooking Pienza

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




