Cortona vacation rentals

We found 3,206 vacation rentals — enter your dates for availability

Select from 279 houses, 349 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

Showing deals for:Jan 30 - Feb 6
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Find out more about Cortona

Why visit Cortona

  • Rich cultural heritage: Discover captivating churches, charming piazzas, and intriguing museums that showcase Cortona's history.
  • Outdoor adventures: Enjoy scenic hikes and explore the beautiful landscapes surrounding this enchanting town.
  • Romantic atmosphere: Experience the quaint charm of Cortona, perfect for couples seeking a romantic getaway.
  • Welcoming locals: Connect with friendly residents who enhance your travel experience with their warmth and hospitality.
  • Diverse accommodations: Choose from luxury villas to cozy apartments for a memorable stay in this picturesque region.

Popular types of accommodation in Cortona

Planning a getaway to Cortona? The next exciting step is selecting your perfect home away from home. Discover a variety of vacation rentals, including stunning villas, cozy private homes, and charming apartments. Whether you're seeking luxury villa rentals or comfortable house rentals, Cortona has something to suit every traveler's needs. Explore the best options and enjoy a memorable stay in this beautiful Italian destination.

  • Villas: Experience luxurious living with spacious villas, perfect for families or larger groups seeking relaxation and stunning views in Cortona.
  • Houses: Enjoy the comfort and convenience of private homes, ideal for families or friends wanting a cozy and personalized stay.
  • Apartments: Opt for modern apartments that offer a blend of comfort and accessibility, great for couples or solo travelers exploring the city.
  • Cottages: Delight in charming cottages that provide a rustic feel and a peaceful retreat amidst the beautiful Tuscan countryside.
  • Agritourism: Immerse yourself in local culture and enjoy farm stays that offer authentic experiences and fresh produce right from the source.**

Top attractions in and around Cortona

Cortona, Tuscany, offers a perfect blend of outdoor adventures, romance, and rich cultural experiences. Visitors can explore captivating churches, charming piazzas, and intriguing museums, making it an ideal destination for those seeking a city experience infused with history and beauty. Whether you're traveling solo, with family, or as a couple, you'll find plenty of attractions to enjoy both within and around this enchanting town.

  • Lake Trasimeno: Located 11 miles from Cortona, this picturesque lake offers stunning scenery, serene beaches, and a romantic atmosphere. Ideal for outdoor activities like swimming, kayaking, and picnicking, it's a perfect escape into nature.
  • Villa Bramasole: Nestled in the heart of Cortona, this historic villa showcases rich cultural heritage. Its beautiful architecture and gardens provide a glimpse into Tuscany's artistic past, making it a must-see for history buffs.
  • Piazza della Repubblica: This vibrant square in Cortona is a cultural hub filled with lively cafes and shops. The surrounding architecture reflects the city's history, offering a charming atmosphere to relax and soak in the local vibe.

Things to do recommended for couples

For a romantic getaway in Cortona, indulge in luxury at the Tennis Club Castiglionese. Savor delightful wines at Agricola Buccelletti Winery, known for its charming atmosphere, or explore the enchanting Fattoria Le Capezzine, where romance meets the great outdoors, all within a short drive from town.

Things to do recommended for families

Families visiting Cortona can explore the beautiful Parco delle Foreste Casentinesi, perfect for nature walks, or enjoy a fun cooking class to learn how to make authentic Italian pasta together. Don't miss the local gelato shops for a sweet treat after your adventures.

Things to do recommended for groups

Groups visiting Cortona can enjoy shopping at the Valdichiana Outlet Village, experience the cultural charm of the Signorelli Theatre, and embark on an adventurous hike along Hannibal's Journey, taking in breathtaking outdoor scenery just a short distance away from the town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether it's with a group, family, or pets, or if you're considering extended stays—be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cortona with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Cortona with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with amenities that suit their age, like a private 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 trip isn’t truly finished without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cortona: If you're in search of vacation rentals offering discounts for month-long stays, 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Cortona

Discover the enchanting charm of Cortona, Tuscany, where outdoor adventures and romantic escapes await. Explore the welcoming streets filled with history and culture, and unwind in a cozy vacation home or rustic farmhouse. Enjoy nearby excursions that lead you to beautiful beaches and captivating landscapes, making Cortona the perfect getaway for travelers seeking relaxation and connection with friendly locals. Experience the magic of this picturesque region on your unforgettable vacation.

  • Cortona Old Town: Nestled in the heart of Tuscany, Cortona Old Town enchants visitors with its rich history and stunning vistas. This charming neighborhood is renowned for its culture-themed experiences and romantic atmosphere, making it a perfect getaway for couples. Explore narrow cobblestone streets lined with historic buildings, visit the picturesque lake nearby, or indulge in local spa treatments. The town is also home to a variety of theaters showcasing local art performances, creating an immersive cultural experience that captures the essence of Tuscany.
  • Camucia: Just a stone's throw from Cortona, the village of Camucia offers a delightful blend of culture and outdoor activities. Known for its scenic beauty, travelers flock to Camucia for its romantic ambiance and vibrant local experiences. Enjoy a leisurely stroll across historic bridges, take in the charm of the local theaters, or play a round of golf at nearby courses. With its close proximity to Cortona, Camucia serves as an ideal base for exploring the region while immersing yourself in its rich history and picturesque landscapes.
  • Castiglion Fiorentino: Located a short drive from Cortona, Castiglion Fiorentino is a captivating city that invites exploration. Known for its outdoor attractions and romantic settings, visitors can unwind at local spas or enjoy body treatments while soaking in the stunning views of the surrounding countryside. The city boasts historic sites, including ancient bridges and scenic lakes, providing a perfect backdrop for leisurely walks. Castiglion Fiorentino's charming atmosphere and rich cultural experiences make it a must-visit destination in Tuscany.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageSlightly High
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 SunnyAverageAverage
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

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can significantly impact prices. Plus, extending your stay often results in even greater savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental. Happy travels.

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Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you can immediately access exclusive member discounts and earn OneKeyCash on eligible reservations. Sign up today to start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your travel effortlessly. You can create new trips, refine your plans, or manage your existing bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips, making it easier for you to stay organized. To check out the Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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?
When choosing the best area to stay in Cortona, Tuscany, one highly recommended neighborhood is the historic center. This charming area is characterized by its narrow, winding streets and picturesque architecture, offering a quintessential Tuscan experience. Staying here places you within walking distance of top attractions such as the stunning Basilica di Santa Margherita, which is perched on a hill and provides breathtaking views of the surrounding countryside, and the Museo Diocesano, where you can discover fascinating local art and history.

Another delightful option is the area around the Parterre Gardens. This neighborhood is slightly more tranquil yet still close enough to the center to enjoy its vibrancy. The Parterre Gardens themselves are a lovely spot for relaxation, and they offer some of the best panoramic views of the Valdichiana.
How much does it cost to rent a vacation home in Cortona?
Prices for vacation rentals in Cortona vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cortona to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cortona vacation house rentals?
You can find great discounts on house rentals in Cortona on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Cortona?
In Cortona, villas are the most popular type of vacation rental, with approximately 409 available throughout the area. These stunning properties often feature traditional Tuscan architecture, spacious interiors, private gardens, and outdoor terraces, superb for enjoying the breathtaking views of the surrounding countryside. Many villas come equipped with amenities such as swimming pools, fully equipped kitchens, and cozy living areas, creating an inclusive setting for relaxation.

Apartments are also a favored option, with around 309 in various neighborhoods, providing travelers with a more intimate experience. These typically include modern amenities like free Wi-Fi, kitchen facilities, and comfortable living spaces, all within walking distance of Cortona's charming historic center, where visitors can explore local shops and restaurants.

Vacation houses, numbering around 226, offer additional space and privacy, ideal for families or larger groups. These properties often come with features such as multiple bedrooms, outdoor dining areas, and easy access to nearby attractions, allowing guests to enjoy the best of Tuscan life.
Are there any family house rentals in Cortona?
In Cortona, Tuscany, there is a wealth of family-friendly house rentals available—specifically, around 539 options. This charming hillside town is renowned for its picturesque views, rich history, and vibrant local culture, making it an excellent choice for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor terraces or gardens where children can play and families can enjoy al fresco dining.

Visitors can explore the historic center, which is filled with quaint shops, delightful cafes, and cultural attractions such as the Etruscan Academy Museum and the stunning Church of San Francesco. The nearby countryside also offers opportunities for outdoor activities, such as hiking and biking, as well as visits to local vineyards and olive groves, enriching the overall experience for families.
Can I rent a vacation home with a pool or hot tub in Cortona?
In Cortona, Tuscany, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 667 options to choose from. This picturesque town is located in the rolling hills of Tuscany, providing a stunning backdrop for a relaxing getaway. Many of these rentals come with private pools, outdoor terraces, and beautifully landscaped gardens, superb for soaking up the sun and enjoying the tranquil surroundings.

Travelers can also expect amenities such as fully equipped kitchens, spacious living areas, and sometimes even hot tubs for ultimate relaxation. The charming historic center of Cortona, with its cobblestone streets and local eateries, is easily accessible, allowing guests to immerse themselves in the local culture while enjoying the comforts of their rental. Find your rental in Cortona with a pool or a hot tub.
Can I find long-stay vacation rentals in Cortona?
A long-stay vacation rental in Cortona is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Cortona?
In Cortona, Tuscany, travelers will find a wide selection of pet-friendly house rentals, with over 500 options available to choose from. Many of these vacation homes offer charming rustic decor, spacious living areas, and fully equipped kitchens, great for families or groups looking to experience the beauty of the Tuscan countryside. Guests can expect amenities such as private gardens, outdoor terraces, and even swimming pools in some properties, providing a delightful setting for relaxation after a day of exploring.

The town itself is rich in history and culture, with its picturesque streets and stunning views of the surrounding hills. Pet owners can also enjoy nearby parks and open spaces, making it a great destination for those traveling with pets. The area offers numerous walking trails and scenic spots where pets are welcome, allowing visitors to fully immerse themselves in the natural beauty of Tuscany while enjoying quality time with their furry companions.
Are there any remote work vacation rentals in Cortona?
In Cortona, Tuscany, there are numerous remote work-friendly vacation rentals available, totaling around 836 options. This picturesque town, known for its stunning hilltop views and rich Etruscan heritage, provides an ideal backdrop for blending work and leisure. Many properties cater specifically to remote workers, featuring amenities such as high-speed Wi-Fi, dedicated office spaces with desks and comfortable chairs, and even laptop-compatible safes for security.

Travelers can expect a variety of accommodations, from charming apartments in the historic center to spacious villas with scenic views. Some properties also offer access to business centers or meeting rooms, making them suitable for those who require a more formal working environment.

Cortona's vibrant atmosphere is complemented by local cafes and restaurants, providing excellent spots for a change of scenery during work breaks. Additionally, the town is surrounded by beautiful landscapes, superb for outdoor exploration once the workday is done. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cortona vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cortona with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cortona?
In Cortona, popular vacation rental amenities include WiFi, kitchens, and private pools, suiting travelers seeking comfort during their stay in this picturesque Tuscan town. Many rentals also feature communal pools, allowing guests to relax and enjoy the warm Mediterranean climate. Additionally, coffee and tea makers are commonly found in these properties, ensuring visitors can savor their morning beverages while taking in the stunning views of the surrounding countryside.
When is the best time to visit Cortona for a vacation rental?
April is the most popular time to visit Cortona, Tuscany, as spring breathes new life into this charming hilltop town. During this month, visitors can revel in the mild weather, with temperatures typically ranging from the mid-40s to low 70s Fahrenheit, making it great for outdoor activities and leisurely strolls through the picturesque streets lined with medieval architecture.

As the peak season runs from July to September, travelers eager for a vibrant atmosphere and bustling activity will find the summer months particularly appealing. However, this period can be quite warm, with temperatures often soaring into the high 80s and low 90s Fahrenheit. While summer offers lively festivals and an abundance of outdoor dining options, many visitors prefer the pleasant climate of spring for a more comfortable experience during their excursions.

For those looking for a more budget-friendly option, October presents a wonderful opportunity to visit Cortona. The fall foliage adds a beautiful touch to the Tuscan landscape, and the crowds have thinned out, allowing for a more relaxed exploration of the town and its surroundings. You can enjoy the local harvest festivals and savor the rich flavors of seasonal cuisine without the summer hustle.

Ultimately, the best time to book a vacation rental in Cortona hinges on your travel preferences—whether you desire the vibrant energy of summer or the serene beauty of spring and fall.
How early should I book a Cortona vacation rental?
Book your Cortona vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cortona?
In Cortona, visitors can experience firsthand the town's rich history and stunning landscapes. The historic center is a must-see, featuring the beautiful Piazza della Repubblica, lined with charming cafes and shops. Nearby, the Diocesan Museum showcases significant works of art, including pieces by Fra Angelico.

For breathtaking views, the scenic Parterre Park offers a panoramic vista of the surrounding countryside and Lake Trasimeno. The Etruscan Academy Museum of the City of Cortona is another highlight, providing insights into the ancient civilization that once thrived in the area.

Travelers can also explore the picturesque streets filled with medieval architecture, leading to the impressive Church of San Francesco, famous for its serene atmosphere and beautiful artworks.
Can I change or cancel my Cortona home rental booking on Vrbo?
To find Cortona vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Cortona vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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