Cortona Old Town holiday lettings

We found 321 holiday rentals — enter your dates for availability

Discover a selection of 27 homes, 163 apartments and other holiday rentals in Cortona Old Town that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the amenities that you expect and more, such as parking and air conditioning. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Cortona Old Town

Showing deals for:23 Jan - 30 Jan

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Interior
9.6 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Cortona, Toscana

12% off
Price is £844
for 7 nights, 1 home
£121 per night
includes taxes & fees

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Why visit Cortona Old Town

  • Medieval charm: Wander through cobbled streets and soak in the enchanting atmosphere of Cortona's historic centre.
  • Stunning churches: Visit remarkable churches that showcase the rich cultural heritage of the town.
  • Picturesque piazzas: Relax in beautiful piazzas, perfect for enjoying a coffee and people-watching.
  • Scenic outdoor adventures: Explore the nearby serene lakes and Tuscan landscapes, ideal for outdoor activities.
  • Charming accommodations: Choose from luxurious villas and stylish apartments for a memorable stay in Cortona.

Popular types of accommodation around Cortona Old Town

If you're contemplating a stay in Cortona Old Town, you're in for a treat! Our selection of holiday rentals includes charming villas, houses, and stylish apartments. Whether you're dreaming of a luxurious villa today or a quaint palazzo pretorio, our Cortona Old Town vacation homes promise an unforgettable experience. Discover the perfect base for your Italian getaway!

  • Villas: The top choice for holiday rentals in Cortona Old Town, offering spacious accommodations with stunning views and luxurious amenities.
  • Houses: A popular option for those seeking a homely atmosphere, these properties provide privacy and comfort for families and groups.
  • Apartments: Ideal for couples or solo travelers, these self-contained units offer convenience in the heart of Cortona.
  • Cottages: Quaint and charming, these delightful retreats are perfect for a peaceful getaway.
  • Agritourism: Experience authentic Tuscan life by staying on a working farm, complete with local produce and scenic landscapes.**

Top attractions in and around Cortona Old Town

Cortona Old Town is a delightful destination for culture enthusiasts and romantics alike, offering a captivating mix of medieval charm and scenic beauty. Explore the historic centre, visit stunning churches, and relax in picturesque piazzas. Don't miss the serene lakes nearby, perfect for outdoor adventures. Whether you're wandering through cobbled streets or soaking in local history, Cortona promises a memorable experience for every traveller.

  • Lake Trasimeno: A stunning lake located 6.8km from Cortona, Lake Trasimeno is perfect for outdoor lovers. With its picturesque beaches and romantic scenery, it's an ideal spot for leisurely walks, picnics, or simply soaking in the natural beauty.
  • Villa Bramasole: This historic villa, situated just 249m from Cortona, embodies the essence of Tuscan culture. Its architectural charm and serene surroundings make it a delightful place to explore the region's rich history.
  • Piazza della Repubblica: Located within Cortona Old Town, this vibrant square is a cultural hub. Surrounded by quaint shops and cafes, it's the perfect place to immerse yourself in local life and history.

Things to do recommended for couples

For a romantic getaway in Cortona Old Town, indulge in luxury at the Tennis Club Castiglionese, enjoy the enchanting atmosphere at Agricola Buccelletti Winery, or unwind amidst the scenic beauty at Fattoria Le Capezzine. Each offers a unique blend of romance and entertainment just a short drive away.

Things to do recommended for families

Families exploring Cortona Old Town can delight in a visit to the Museo dell'Accademia Etrusca, where children can learn about ancient history through engaging exhibits. Additionally, the nearby Parco del Lago Trasimeno offers picturesque walking trails and playgrounds, perfect for a family picnic or leisurely stroll.

Things to do recommended for groups

Experience the charm of Cortona Old Town by enjoying a performance at Signorelli Theatre, indulging in retail therapy at Valdichiana Outlet Village, or embarking on an adventurous hike along Hannibal's Journey, where stunning scenery awaits just 3.1km away.

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 an extended stay, it's important to filter your options according to your key preferences. Here are some helpful booking tips for using Vrbo.

  • 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 areas for socialising. Thankfully, you can filter for all of these options and more on Vrbo.
  • Traveling to Cortona Old Town with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise 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 attractions that are suitable for families.
  • Taking your pets with you to Cortona Old Town: For many families, a holiday just isn’t quite right without their beloved pet. If that resonates with you, take a look at Vrbo accommodations that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Cortona Old Town: If you're seeking holiday rentals with discounts 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 accommodations. You might also want to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Cortona Old Town

Cortona Old Town offers a delightful blend of rich history and charming medieval streets, making it an ideal destination for culture enthusiasts and romantics alike. Explore the historic town's enchanting atmosphere, where friendly locals welcome you to indulge in luxurious experiences. Nearby, you can discover the stunning landscapes of Tuscany, perfect for outdoor excursions. Whether you're wandering through cobblestone alleys or enjoying the breathtaking views, Cortona promises a memorable holiday.

  • Cortona: Nestled a mere 186m from Cortona Old Town, this charming city offers a delightful blend of outdoor, romantic, and cultural experiences. Visitors can indulge in rejuvenating spa treatments or enjoy captivating performances at local theatres. The scenic landscape features picturesque lakes and historical sites, including impressive bridges that tell tales of Cortona's rich past. A stroll through its winding streets reveals a wealth of artistic and architectural heritage, making it an essential stop for any traveller.
  • Camucia: Located approximately 621m from Cortona Old Town, Camucia is a quaint village perfect for those seeking cultural, romantic, and outdoor experiences. The village’s vibrant theatre scene is complemented by outdoor activities and nearby golf courses, catering to a variety of interests. Visitors can marvel at the historic bridges and charming landmarks that define the village's character, along with the enchanting historic places that whisper stories of bygone eras.
  • Casorbica-Salcotto: Just 559m away from Cortona Old Town, the village of Casorbica-Salcotto invites you to explore its outdoor, cultural, and city-themed experiences. Ideal for swimming enthusiasts and shoppers alike, this village features a lively square and a welcoming visitor centre. The piazza square serves as a social hub where locals gather, offering an authentic glimpse into daily life. With its inviting atmosphere and proximity to stunning landscapes, Casorbica-Salcotto is a hidden gem worth discovering.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, booking a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up right where you left off, or easily view and organise your travel arrangements. You can now find the properties you’ve saved and booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Cortona Old Town?
In Cortona Old Town, apartments are the most popular type of holiday rental, with around 144 available throughout the charming, historic streets. These apartments typically feature fully equipped kitchens, comfortable living areas, and often include balconies or terraces that provide lovely views of the surrounding Tuscan landscape. The proximity to points of interest such as the Piazza della Repubblica and the Etruscan Academy makes these rentals especially appealing for travellers looking to immerse themselves in the local culture.
How much does it cost to rent a holiday home in Cortona Old Town?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cortona Old Town holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Cortona Old Town?
A long-stay holiday 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 holiday rental?
April is the most popular time to visit Cortona Old Town, as the weather begins to warm up and the picturesque surroundings come alive with vibrant spring blooms. During this month, temperatures typically linger in the low to mid-teens Celsius, creating a pleasant atmosphere for outdoor activities and leisurely strolls through the charming streets of this Tuscan gem.

From July to September, the peak season draws visitors keen to soak in the sun and indulge in the region's rich cultural offerings. While this period is bustling with tourists, it also presents a wonderful opportunity for those who enjoy lively festivals, outdoor dining, and the chance to explore the stunning countryside.

For those seeking a more budget-friendly experience, consider visiting in January. Although it's a quieter time in Cortona, the tranquillity allows for a more intimate connection with this historic town. You can enjoy the beautiful architecture and explore local shops without the crowds, all while experiencing the charm of an Italian winter.
Are there any remote work holiday rentals in Cortona Old Town?
In Cortona Old Town, there are numerous remote work holiday rentals available, with around 175 options to choose from. This enchanting Tuscan town offers a picturesque setting for those looking to combine work with leisure. Many of the properties come equipped with essential amenities for remote work, including 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 holiday rental?
Book your Cortona Old Town holiday 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 holiday 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 immerse themselves in a rich tapestry of history and culture. The town's medieval architecture is best appreciated at the Piazza della Repubblica, where the beautiful Palazzo Comunale stands. Nearby, the Diocesan Museum of Sacred Art showcases an impressive collection of religious artifacts and artworks.

For those who enjoy stunning views, the Basilica di Santa Margherita is a must-visit, perched on the highest point of the town, offering panoramic vistas of the surrounding countryside. The charming streets of Cortona are lined with local shops and traditional trattorias, superb for sampling Tuscan cuisine.
Can I change or cancel my Cortona Old Town home rental booking on Vrbo?
To find Cortona Old Town holiday 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 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 Old Town holiday 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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