
Vacation rentals in Cortona
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Top-rated vacation rentals in Cortona
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Casa Lucy
House located on the Cortonese hill, completely renovated, consisting of 3 double bedrooms, 2 bathrooms and an open space kitchen and dining room. It is located 5 minutes from the historic center of Cortona and in an excellent position to reach the most beautiful and characteristic places of Tuscany and Umbria such as Pienza, Montepulciano, Castiglione del Lago up to cities that are cradles of art such as Florence, Arezzo, Siena and Perugia. Mandatory tourist tax to be paid on site (€2.50 per person for 4 days)
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Cortona’s Rooftop Nest
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 accommodates 4 people. Fans in the bedrooms The apartment is located in the historic center right in front of the wonderful church of St. Francis and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can accommodate up to 4 people. Fans in the rooms.
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Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
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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.
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Casa Dolce Toscana | Panoramic Suite with a View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.
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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.
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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.
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CasaNella: central, bright, 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.
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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!
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Cortona Shabby Chic House - independent & balcony-
This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation
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Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
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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"
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Popular amenities for Cortona vacation rentals
Boutique hotels in Cortona

Nice double room in a charming B&B
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Borgo Iesolana Country Retreat Suite with terrace
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Boutique room - Tower - From Hill to Hill
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Agriturismo Merigge Wellness & Spa Montepulciano
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Room in Historical Residence, Abbey, farmhouse

Romantic Living!
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Mustiola - Deluxe Suite with outdoor patio
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Rossellino® - Suite (Double Bed) 2nd Floor
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Other great vacation rentals in Cortona

Under the sunset, Montepulciano
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Casale Santa Barbara - Exclusive Apartment
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Mascagni Farmhouse in Val d'Orcia, Pienza
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Luxurious Medieval Tower & Private Concierge
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Poggio Bicchieri Holiday Farm - Memoria apartment
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Farmhouse Fattoria La Parita
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Breathtaking views: Historic House w/Terrace & BBQ
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Casa Primo Stylish-townhouse w/ patio & jetted tub
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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
- Lake Trasimeno
- Lake Bolsena
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Del Chianti
- Piazzale Michelangelo
- Basilica of St Francis
- Boboli's Garden
- Centro Storico Orvieto
- Mount Amiata
- Stadio Artemio Franchi
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- Antinori nel Chianti Classico
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Mount Subasio
- Valdichiana Outlet Village
- Firenze Campo di Marte
- Casa Barthel
- Gola del Furlo





