Cortona Old Town vacation rentals

We found 282 vacation rentals — enter your dates for availability

Discover a selection of 27 homes, 152 apartments, and other vacation rentals in Cortona Old Town that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Cortona Old Town

Why visit Cortona Old Town

  1. Charming Streets: Wander through ancient cobblestone pathways lined with vibrant piazzas and stunning churches.
  2. Historic Landmarks: Discover the rich history of Cortona by visiting its impressive palaces and monuments.
  3. Scenic Vistas: Enjoy breathtaking views of the surrounding Tuscany landscape from this picturesque hilltop town.
  4. Local Cuisine: Savor authentic Tuscan dishes in delightful eateries, experiencing the region's culinary delights.
  5. Outdoor Adventures: Explore nearby excursions and immerse yourself in the natural beauty of Tuscany.

Popular types of accommodation around Cortona Old Town

You've chosen the charming Cortona Old Town for your next getaway, and now it’s time to find the perfect place to stay. From stunning villas to cozy houses and inviting apartments, you’ll have a variety of accommodation options. Consider the delightful Villa Cozzano or the quaint Loggetta Cortona, both offering free Wi-Fi and breakfast to make your stay even more enjoyable.

  • Villas: Experience the charm of Cortona Old Town by staying in luxurious villas, offering spacious accommodations and stunning views.
  • Houses: Ideal for families and friends, these homes provide a comfortable and private retreat with all the amenities.
  • Apartments: Enjoy the convenience of modern apartments, perfect for a city vibe while exploring the local culture.
  • Cottages: For a quaint and cozy experience, choose charming cottages that offer a touch of rustic charm.
  • Caravan Parks: A budget-friendly option, caravan parks allow you to connect with nature while enjoying the outdoors.**

Top attractions around Cortona Old Town

Cortona Old Town offers a romantic and culturally rich vacation experience, perfect for outdoor enthusiasts and history buffs alike. Explore stunning churches, vibrant piazzas, and historic palaces while taking leisurely strolls through the charming streets. Don't miss the chance to embark on a tour of Cortona and the beautiful Tuscany region, ensuring you soak up all the local sights and culture during your visit.

  1. Lake Trasimeno: A picturesque lake 17.7km from Cortona, perfect for romantic strolls, scenic views, and outdoor activities. Enjoy the beach vibes and tranquil atmosphere.
  2. Villa Bramasole: A historic villa located only 644m from Cortona, rich in culture and steeped in history. Its stunning architecture offers a glimpse into the region's artistic heritage.
  3. Piazza della Repubblica: The heart of Cortona Old Town, this vibrant square showcases local culture and bustling city life, surrounded by charming cafes and historic buildings.

Things to do recommended for couples

Ready for a romantic getaway in Cortona Old Town? Enjoy luxury vibes at the Tennis Club Castiglionese, sip fine wines at Agricola Buccelletti Winery, or relish the outdoor charm at Fattoria Le Capezzine. Each spot promises a memorable experience for couples seeking romance and adventure.

Things to do recommended for groups

Your group can enjoy a captivating evening at the Signorelli Theatre, indulge in shopping at the Valdichiana Outlet Village, or embark on an adventurous hike along Hannibal's Journey, all while soaking in the rich culture and beautiful scenery of Cortona Old Town.

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

When you're planning a trip—whether it's with a group, your family, or even your pets, or if you're considering a longer stay—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cortona Old Town with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Cortona Old Town with young kids: Traveling with young children can present its challenges. 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 Old Town: For many, a family getaway wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Cortona Old Town: If you’re in search of vacation rentals that offer great deals 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay around Cortona Old Town

Cortona Old Town offers a delightful blend of culture, history, and romance. Nestled on a picturesque hill, this charming neighbourhood invites you to discover its ancient streets, stunning vistas, and friendly atmosphere. Explore the beauty of Cortona as you stroll through its historical sites, indulge in local cuisine, and soak in the relaxing vibes. Nearby, the surrounding region promises exciting excursions, making it a perfect destination for a memorable vacation.

  • Camucia: Located a mile from Cortona Old Town, Camucia is a charming village that invites visitors to immerse themselves in Tuscan culture and romance. The area is perfect for outdoor enthusiasts, offering activities like golf and scenic walking trails. You can enjoy the local theatre scene or visit historic landmarks, including an impressive historic bridge and other notable sites. The blend of cultural experiences and natural beauty makes Camucia a delightful stop for those seeking a relaxed yet enriching travel experience.
  • Casorbica-Salcotto: Just 1.4km from Cortona Old Town, Casorbica-Salcotto is a quaint village that richly embodies the outdoor and cultural spirit of Tuscany. Visitors can indulge in swimming and shopping, making it a great place for leisurely exploration. The picturesque piazza and vibrant visitor centre serve as central points for social gatherings and cultural events. With its inviting atmosphere and local charm, Casorbica-Salcotto provides an authentic taste of Italian village life.
  • Sodo: Also located 1.4km from Cortona Old Town, Sodo is a lively village that offers a blend of entertainment and cultural experiences. The area features shopping centres and malls, making it ideal for shoppers looking to discover local products and souvenirs. You can explore historic bridges and landmarks that tell the story of the region’s rich past. Sodo's vibrant community and its blend of modern conveniences and historical allure make it a must-visit destination during your Tuscan adventure.

Best time to go to Cortona Old Town

If you're planning a trip to Cortona Old Town, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like January to February and November 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 CloudyLowAverage
February41.2°F (5.1°C)Light RainMostly SunnyLowSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
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)SunnyHighSlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnyHighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyHighAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyLowSlightly Low
December41.7°F (5.4°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you could enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new journeys, manage your existing plans, or review and organize your bookings. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips. To explore the features of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Cortona Old Town?
In Cortona Old Town, apartments are the most popular type of vacation rental, with approximately 144 available throughout the historic centre. These apartments are typically located in charming, ancient buildings and offer amenities such as fully equipped kitchens, cosy living areas, and often stunning views of the surrounding Tuscan countryside. Many also feature outdoor terraces or balconies, superb for enjoying the local atmosphere.
How much does it cost to rent a vacation home in Cortona Old Town?
Prices for vacation rentals in Cortona Old Town 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cortona Old Town to more spacious homes.
Are there any discounts for Cortona Old Town vacation house rentals?
You can find great discounts on house rentals in Cortona Old Town 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.
Are there any Cortona Old Town vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cortona Old Town with parking available—perfect for families or travellers 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.
Can I find long-stay vacation rentals in Cortona Old Town?
A long-stay vacation rental in Cortona Old Town is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Cortona Old Town for a vacation rental?
April is a delightful time to visit Cortona Old Town, as the spring blooms breathe new life into this charming Tuscan town. During this month, the weather is pleasantly mild, typically hovering around 15-20 degrees Celsius, making it ideal for leisurely strolls through the picturesque streets and exploring the rich history and culture of the area.

As you venture through Cortona, you can enjoy outdoor activities such as hiking in the surrounding hills or visiting local vineyards, which are particularly inviting during the spring season. The vibrant landscape, coupled with fewer crowds, allows for a more intimate experience, great for those seeking to immerse themselves in the local atmosphere.

The peak season runs from July to September, when the town buzzes with tourists eager to soak up the sun and enjoy various festivals. While this is a lively time filled with events, it can also lead to higher accommodation prices and busier attractions. If you're looking for a more relaxed experience with the charm of Tuscany, April offers a fantastic balance of pleasant weather and activities without the summer rush.

For budget-conscious travellers, consider visiting in January, which is the low season. While the temperatures can be cooler, this month unveils Cortona's peaceful charm, allowing you to explore the town at your own pace and appreciate its beauty without the usual crowds.
Are there any remote work vacation rentals in Cortona Old Town?
In Cortona Old Town, there are numerous remote work vacation rentals available, with around 175 options to choose from. This charming Tuscan town offers a superb blend of history and modern amenities, making it an ideal location for those looking to work remotely. Many of the properties are equipped with essential remote work amenities such as Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Cortona Old Town vacation rental?
Book your Cortona Old Town 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 Old Town?
In Cortona Old Town, visitors can experience firsthand the rich history and stunning architecture that the area has to offer. The Piazza della Repubblica serves as a central hub, surrounded by charming cafes and shops, with the imposing Palazzo Comunale standing proudly at one end. Vacation rentals nearby often provide easy access to these vibrant local amenities.

A visit to the Diocesan Museum is a must, showcasing a remarkable collection of art, including works by renowned Italian artists. The area around the museum is filled with narrow, cobbled streets that add to the town's historic charm.

The stunning views from the Basilica di Santa Margherita, perched atop the hill, are another highlight, offering breathtaking panoramas of the surrounding Tuscan countryside. Rentals in this area often boast beautiful terraces or balconies where guests can enjoy sunset views over the hills.
Can I change or cancel my Cortona Old Town home rental booking on Vrbo?
To find Cortona Old Town 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 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 travellers 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 cosy cabin or a beach house, 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 Old Town 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More Vacation Ideas