Cortona vacation rentals

We found 3,093 vacation rentals — enter your dates for availability

Select from 149 houses, 179 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:May 22 - May 29

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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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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, Tuscany, Italy when booking a vacation rental?
When considering the best area to stay in Cortona, Tuscany, a great option is the historic center. This charming neighborhood is characterized by its medieval architecture, cobblestone streets, and stunning views of the surrounding countryside. Staying here means you'll be within walking distance of significant attractions, such as the beautiful Diocesan Museum and the impressive Basilica of Santa Margherita, both of which offer a glimpse into the rich history and culture of the area.

Another delightful area to consider is the outskirts of Cortona, where you can find properties that offer a more tranquil setting while still being close to the town's main attractions. This region is superb for those who enjoy nature walks and the stunning landscapes that Tuscany is famous for. You can easily explore nearby vineyards and olive groves, making it an ideal spot for those looking to immerse themselves in the local lifestyle.

Cortona has a variety of vacation rental options, ranging from cozy apartments in the heart of the city to spacious villas with breathtaking views.
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 around 338 available throughout the area. These spacious properties often come with beautiful gardens, private pools, and stunning views of the Tuscan countryside, making them ideal for larger groups or families looking for a luxurious stay. Apartments follow closely behind, with approximately 288 options scattered across the charming town and surrounding areas, frequently featuring fully equipped kitchens, cozy living spaces, and easy access to local markets and restaurants. Additionally, there are around 180 vacation houses available, which provide a comfortable home-like atmosphere with multiple bedrooms and outdoor spaces for enjoying the serene landscape. Several cottages and chalets can also be found, offering unique and rustic experiences for those seeking a more traditional Tuscan getaway.
Are there any family house rentals in Cortona?
In Cortona, Tuscany, there is an abundance of family-friendly house rentals available—around 505 options to choose from. This charming town is famous for its picturesque streets and stunning views of the surrounding countryside. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor terraces, making them great for family gatherings and meals together.

Visitors can enjoy amenities such as private pools, game rooms, and even gardens where children can play. The area is also close to local attractions, including the Etruscan Academy Museum and the beautiful hilltop views from the town's ancient walls.

Moreover, exploring the nearby towns of Arezzo and Montepulciano offers additional cultural experiences, while the scenic landscapes provide opportunities for outdoor activities like hiking and biking.
Can I rent a vacation home with a pool or hot tub in Cortona?
In Cortona, Tuscany, travelers will find a wide selection of vacation homes available for rent that feature pools and hot tubs, with around 566 options to choose from. This picturesque town, known for its stunning landscapes and rich history, offers a variety of properties in the surrounding countryside and within the charming town itself. Many of these rentals come equipped with private swimming pools, outdoor hot tubs, and spacious terraces that provide breathtaking views of the Tuscan hills.

Expect amenities such as fully equipped kitchens, allowing for the preparation of local Tuscan cuisine, while many properties also include comfortable living areas and outdoor dining spaces, ideal for enjoying meals al fresco. Some homes may feature additional luxuries like gardens, barbecue facilities, and proximity to local wineries and cultural sites, making them superb for families or groups looking to relax and explore the beauty of Tuscany. 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, there are numerous pet-friendly house rentals available, with a total of 445 options for travelers to choose from. Many of these rentals feature traditional Tuscan architecture, offering charming interiors with fully equipped kitchens, spacious living areas, and often outdoor spaces like gardens or terraces where pets can enjoy the fresh air.

The town itself is steeped in history and provides a picturesque setting for both relaxation and exploration. With its cobblestone streets and scenic views of the surrounding countryside, visitors can easily find nearby parks and open spaces suitable for walks with pets. Additionally, Cortona's local eateries and shops are generally welcoming to pets, enhancing the overall experience for those traveling with their furry companions.
Are there any remote work vacation rentals in Cortona?
In Cortona, Tuscany, there are plenty of vacation rentals suitable for remote work, with approximately 759 options available. This picturesque town, known for its stunning hilltop views and rich history, offers a variety of properties equipped with essential amenities for remote workers. Many rentals feature free Wi-Fi, allowing for seamless connectivity, as well as comfortable workspaces within the units.

Travelers can expect accommodations that range from charming apartments in the historic center to spacious villas with breathtaking countryside views. These properties often come with additional comforts such as fully equipped kitchens, safe in-room storage, and outdoor spaces where one can relax after a day of work. 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 rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals while enjoying local produce. Many properties also offer onsite parking, which is convenient for those exploring the picturesque Tuscan countryside. A fireplace is a common feature, providing a cozy atmosphere during cooler evenings. For pet owners, rentals that permit pets are available, making it easier to travel with furry companions. Additionally, several rentals come with private pools, offering a refreshing spot to relax and unwind under the Tuscan sun.
When is the best time to visit Cortona for a vacation rental?
April is the best time to visit Cortona for a vacation rental, as the spring season brings mild temperatures and vibrant blooms throughout the Tuscan landscape. This month is especially appealing for travelers who appreciate outdoor activities, such as exploring the charming streets of Cortona or hiking in the surrounding hills. With temperatures ranging from the mid-50s to low 70s Fahrenheit, the weather is great for leisurely strolls and moments spent admiring the breathtaking views.

While the peak tourist season runs from July to September, when visitors flock to experience the lively summer atmosphere and local festivals, April offers a more tranquil experience. You can enjoy the scenic beauty of the region without the larger crowds, allowing for a more intimate connection with the rich history and culture of Cortona.

For those considering a more budget-friendly option, January is the low season, which may offer better rates but comes with cooler temperatures. However, April provides a delightful blend of comfortable weather and fewer tourists, making it a prime choice for a memorable getaway.
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, Tuscany, Italy?
In Cortona, visitors can immerse themselves in a rich tapestry of history and culture. The town's historic center features the beautiful Piazza della Repubblica, where the striking Palazzo Comunale stands, offering a glimpse into the city's medieval past. Nearby, the Diocesan Museum of Cortona showcases a collection of religious art, including works by renowned artists.

For stunning views of the surrounding countryside, the scenic Eremo Le Celle, a Franciscan hermitage located a short distance from the town, provides a peaceful retreat with breathtaking landscapes.

Art enthusiasts should not miss the opportunity to visit the Museo dell'Accademia Etrusca, which houses an impressive array of Etruscan artifacts and artworks.

Additionally, the Cortona Wine Festival, held annually, attracts visitors keen to explore local wines and culinary delights, making it a highlight for food and wine lovers.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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