Cortona vacation rentals

We found 3,257 vacation rentals — enter your dates for availability

Select from 276 houses, 355 apartments, and other vacation rentals to find the perfect place for your stay in Cortona. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as parking and air conditioning. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Cortona

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Find out more about Cortona

Why visit Cortona

  1. Rich History: Discover Cortona's fascinating museums and historic churches that reflect its vibrant cultural heritage.
  2. Stunning Views: Enjoy breathtaking landscapes and panoramic views that make for perfect photo opportunities.
  3. Charming Neighborhoods: Wander through picturesque streets filled with quaint shops, local art, and delicious cuisine.
  4. Romantic Atmosphere: Experience a romantic getaway in this idyllic Tuscan town, perfect for couples.
  5. Diverse Accommodations: Choose from luxurious villas, rustic farmhouses, or cozy apartments for a memorable stay.

Popular types of accommodation in Cortona

Looking for the perfect getaway in Cortona? You're in the right place! Our most popular vacation rentals include charming apartments, spacious houses, and stunning villas. Whether you're dreaming of a beautiful villa, a cozy farmhouse rental, or a luxurious villa escape, we have a variety of options to suit your needs. Discover the best vacation rentals in Cortona and start planning your unforgettable Italian retreat today!

  • Apartments: The top choice for travelers in Cortona, offering comfortable living spaces with convenient amenities for a home-like feel.
  • Houses: A popular option for families and groups, providing spacious accommodations and a personal touch for your stay.
  • Villas: Luxurious and spacious, these properties offer stunning views and a taste of authentic Tuscan living.
  • Caravan Parks: A unique and budget-friendly way to experience the outdoors, perfect for adventurous travelers.
  • Cottages: Quaint and cozy, these charming retreats are ideal for a peaceful getaway in the countryside.**

Top attractions in Cortona

Cortona, nestled in Tuscany, is an idyllic destination perfect for outdoor enthusiasts, couples, and culture seekers alike. Visitors can explore charming churches, vibrant piazzas, and fascinating museums that showcase the town's rich history. Whether you're looking for a romantic getaway or a cultural adventure, Cortona offers a variety of attractions that will enrich your travel experience in this beautiful Italian locale.

  1. Lake Trasimeno: Located 11 miles from Cortona, Lake Trasimeno offers a romantic escape with beautiful beaches, serene outdoor activities, and stunning scenery. It's perfect for leisurely walks, picnics, or water sports.
  2. Villa Bramasole: Nestled within Cortona, Villa Bramasole is a historic site rich in culture. It's known for its charming architecture and lush gardens, providing a glimpse into the region's artistic heritage.
  3. Piazza della Repubblica: This vibrant square in Cortona is a cultural hub, surrounded by historic buildings and lively cafes. It's an ideal spot to soak up the local atmosphere and enjoy people-watching.

Things to do recommended for couples

Planning a romantic getaway in Cortona? Visit Agricola Buccelletti Winery for a delightful wine experience just 5 miles away, or indulge in luxury at Tennis Club Castiglionese. Don't miss Fattoria Le Capezzine, a charming winery 7 miles from Cortona, offering outdoor fun and enchanting vibes.

Things to do recommended for groups

Your group can enjoy a shopping spree at Valdichiana Outlet Village, hike the scenic trails of Hannibal's Journey, and experience the cultural charm of Signorelli Theatre in Cortona. Each activity offers a unique blend of adventure, entertainment, and local vibes perfect for group travelers.

What do I need to keep in mind when booking a vacation in Cortona

If you're planning a trip with a group, traveling as a family, bringing along your pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Cortona with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many others on Vrbo.
  • Traveling to Cortona with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cortona: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Cortona: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Cortona

Experience the charm of Cortona, Tuscany, where romance meets culture amidst stunning views. This picturesque town and its welcoming surroundings offer a perfect getaway for outdoor enthusiasts and history lovers alike. Explore charming neighborhoods, indulge in local cuisine, and soak in the tranquil atmosphere. Whether you're seeking a luxury escape or a secluded retreat, Cortona promises an unforgettable holiday filled with beautiful landscapes and rich heritage.

  • Montepulciano: Located 16 miles from Cortona, Montepulciano is a hilltop town renowned for its stunning landscapes and rich cultural heritage. Visitors are drawn to its charming medieval streets and Renaissance architecture, making it a perfect spot for romantic getaways and outdoor exploration. Popular activities include indulging in spa treatments and enjoying the local shopping scene. Notable attractions include historic monuments and the picturesque Lake Montepulciano, which offers a serene backdrop for relaxation and scenic walks.
  • Perugia: Perugia, situated 23 miles from Cortona, is celebrated for its vibrant arts scene and historic charm. This city is a hub for culture lovers and outdoor enthusiasts alike, featuring a variety of educational and spa experiences. As you explore the cobblestone streets, you’ll encounter captivating historic sites, including ancient churches and museums. The beautiful Lake Trasimeno is nearby, providing opportunities for leisurely activities like boating and picnicking amidst nature's beauty.
  • Arezzo: Just 14 miles from Cortona, Arezzo is a cultural treasure trove that offers an enchanting mix of history and romance. The city is famous for its bustling piazzas and historic landmarks, making it a must-visit for those interested in art and architecture. Visitors can enjoy spa and body treatments while also taking in the local arena entertainment. Don’t miss the opportunity to explore Arezzo's historic sites, where the past comes alive through stunning architecture and vibrant local life.

Best time to go to Cortona

If you're planning a trip to Cortona, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and July to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.2°F (4.0°C)Light RainMostly CloudySlightly LowAverage
February41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnySlightly HighAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageAverage
July74.8°F (23.8°C)No Rain (Dry)SunnySlightly HighSlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageSlightly High
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly Low
December41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Planning to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for an extended stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire reservation. Being the planner truly has its rewards! When you enroll in our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your next adventures. You can easily create new trips, continue from where you last stopped, or organize your travel plans all in one place. Your saved or booked properties will be neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Medieval magic in Cortona

Tucked in the southern region of Tuscany, Cortona dazzles with its ancient stone walls, medieval architecture and spectacular views from its prime hilltop location. Cortona vacation rentals provide an excellent base for exploring exquisitely preserved religious sites, tasting the spectacular wines of the region or taking a class on traditional Tuscan cuisine. There are museums to inspire, with the fascinating history of the many cultures that have thrived in Cortona, and, at the end of the day, you can watch the sunset over surrounding hills, as you sip wine and watch people from a comfortable seat in a piazza.

A hilltop fortress in Cortona

Housed in a gorgeous 13th-century palazzo, the Museo dell'Accademia Etrusca e della Città di Cortona is a riveting museum, filled with Roman and Etruscan treasures unearthed from the surrounding area. For staggeringly beautiful views of Tuscany and Umbria, the Medici fortress, Fortezza del Girifalco, cannot be beaten. Once you've soaked up the view, you can stay for a falconry show or dinner concert. The Eremo Francescano Le Celle, a Franciscan hermitage, is a short drive from Cortona vacation rentals. Nestled in the woods across an old stone bridge, it's a place of stillness broken only by the toll of bells.

History and art in Cortona

Lovers of history will find myriad delights in the medieval city of Cortona. The old walls of Cortona hold a wealth of stories, with a history incorporating the ancient Etruscans, the Romans, the powerful Medici family and Francis of Assisi, Cortona vacation rentals are within walking distance of many of Cortona's most important sites. Art lovers will find much to inspire in museums and galleries, while shoppers can wander the narrow streets to find treasures of local wines, produce and crafts. For a break from the heat, take a refreshing dip in the waters of nearby Lake Trasimeno.

Springtime beauty in Cortona

If you want to explore the medieval beauties of Cortona without sweltering or shivering, spring is the best time of year to visit. April and May are ideal, with warm, sunny afternoons for wandering the cobbled streets, and cool mornings to explore the nearby hills, carpeted in wild flowers. Summer is a beautiful time to visit Cortona, but the temperatures soar, so be sure to wear a hat and keep hydrated. Fall is great for sampling the bounty of Cortona, and winter, although chilly, is still a beautiful time to stay in Cortona and take daytrips for downhill skiing.

Hillside wonders and wildlife in Cortona

Cortona is perched on a hilltop, with stunning views of a countryside marked by rolling hills and verdant farmland. Around 2 hours east of the Adriatic Sea and 2 hours west of the Tyrrhenian Sea, Cortona is ideally situated for those who want to experience medieval architecture, rural idylls and seaside excursions. Cortona is known more for food and wine than wildlife, but those who venture out of the city and into the countryside will have the opportunity to see wild animals. Trekking over the hills affords the best chance to spot wild boar, wolves, porcupines, badgers and red foxes.

Transportation to and around Cortona

The nearest airport is in Sant Egidio Airport (PEG), located 28.9 mi (46.6 km) from the city center.

If you'd rather travel by train, make your way to Camucia-Cortona Station or Terontola-Cortona Station to see more of the city.

Frequently asked questions

What is the best area to stay in Cortona when booking a vacation rental?
Fratticciola is among the most desired neighborhoods to book a vacation property in Cortona. Make yourself at home here to enjoy the relaxation and convenience that comes with having an entire place to yourself.
What is the most popular type of vacation rental accommodation in Cortona?
Villas are the most popular kind of vacation rental in Cortona, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in a variety of shapes and sizes. Filter our options to find your perfect Cortona pad.
How much does it cost to rent a vacation rental in Cortona?
The average price for a vacation rental in Cortona depends on several factors, including time of year, length of stay and property type. Whether you're searching for a sprawling house with room for friends and family or a cozy cabin perfect for just you and the kids, just add your travel dates to view stays with amazing value.
How much does it cost to rent a beach house in Cortona?
Prices for beach houses in Cortona will vary depending on the size and type of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to refine your search by amenities, nearby activities, ratings and more.
Are there pet-friendly vacation rentals in Cortona?
Happily, yes. Pick from 1,063 vacation homes that welcome pets in Cortona on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to find a property where your doggie can get in on the fun.
Can I rent a house with a pool in Cortona?
Check the "pool" box in our handy filter tool and pick from 798 houses with private pools in Cortona on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your vacation property comes with its own swimming pool.
What are popular rental amenities in Cortona?
The most popular rental amenities guests are looking for in Cortona are an electric car charging station, a beach view and a sauna. Whether you're vacationing with pals, family or even pets, Vrbo vacation rentals feature the best amenities for starting a new adventure with the people you love.
Are there large group vacation rentals in Cortona?
There are 283 properties in Cortona that can accommodate 10 or more people. Whether you're planning a vacation with extended family or an event like a party, there's plenty of space to get your group together under the same roof.
Are there vacation rentals in Cortona that welcome kids?
Gather the whole crew for the adventure of a lifetime in Cortona at one of our 1,041 family-friendly properties. A lot of these stays come with amenities that are perfect for trips with youngsters, like laundry facilities, living rooms and outdoor spaces. Just check the "Properties good for families" filter box and choose your favorite option.
What are the top attractions for families in Cortona?
Keep the kids busy at these awesome family-friendly attractions in Cortona:

  • Santa Maria Nuova
  • Santa Maria delle Grazie
  • Museum of the Etruscan Academy

Are there one-bedroom vacation rentals in Cortona?
Yes, there are 223 one-bedroom properties in Cortona to choose from. A one-bedroom vacation rental is an excellent option if it's just you and your sweetheart or if you're traveling alone. Throw in more convenience, space and privacy than a hotel, and you're sure to have a break to remember.
Can I find two-bedroom vacation rentals in Cortona?
You can select from 274 two-bedroom vacation rentals in Cortona. Put the kids in the second room or fill it with a couple of your best friends. There's enough space for whoever's lucky enough to be joining your journey.
Are there vacation rentals with WiFi in Cortona?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 491 vacation homes with WiFi in Cortona. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Cortona?
Decide on your travel dates and then make use of the filters to locate vacation rentals with air conditioning in Cortona on Vrbo. With 684 air-conditioned properties available, you can enjoy a cool and comfy stay.
How old do you have to be to rent a vacation rental in Cortona?
The minimum age permitted can differ across properties on Vrbo, so double-check the rules of the vacation home in Cortona you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Cortona for?
The length of time you can rent a vacation rental in Cortona depends on the property. Simply enter your desired dates to look at a list of options offering extended stays. With lots of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a perfect place to call your home away from home in Cortona.
Does Vrbo offer discounts for vacation homes in Cortona?
In Cortona, you'll find some fantastic bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a mini escape or a much longer stay, we've got a variety of options to match your style.

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