Cortona holiday lettings

We found 3,118 holiday rentals — enter your dates for availability
Select from 152 houses, 204 apartments and other holiday rentals to find the perfect place for your stay in Cortona. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Cortona

Showing deals for:23 Oct - 30 Oct

Image gallery for Private pool, countryside views

Outdoor dining
9.4 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)

Private pool, countryside views

Castiglione del Lago

7% off
Price is £6,713
for 7 nights, 1 villa
£959 per night
includes taxes & fees
Private pool, countryside views

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Why visit Cortona

  • Rich cultural heritage: Explore stunning churches, charming piazzas, and fascinating museums that showcase Cortona's vibrant history.
  • Breathtaking scenery: Enjoy panoramic views of the picturesque Tuscan countryside from the town’s hilltop.
  • Picturesque streets: Wander through charming cobbled streets lined with ancient stone buildings.
  • Local festivals: Experience vibrant celebrations that highlight the town's warm hospitality and rich culture.
  • Delicious local cuisine: Savor exquisite meals at quaint trattorias, enjoying traditional Tuscan flavours.

Popular types of accommodation in Cortona

Welcome to Cortona, a picturesque gem in Tuscany, Italy, where rich history meets stunning landscapes. Explore charming cobbled streets, visit the ancient Etruscan walls, and admire the breathtaking views from the town’s hilltop. Whether you seek luxury villas, quaint apartments, or houses, Cortona offers an array of delightful accommodation options. Immerse yourself in the local culture, savour exquisite cuisine, and discover the enchanting experiences that await you in this captivating city.

  • Villas: Luxurious villas are the top choice for visitors to Cortona, offering spacious accommodations and stunning views.
  • Houses: Ideal for families or groups, private homes provide a homely atmosphere with all the necessary amenities.
  • Apartments: Conveniently located apartments are perfect for those seeking a blend of comfort and local culture.
  • Cottages: Quaint cottages offer a charming and tranquil escape, perfect for a romantic getaway.
  • Agritourism: Experience authentic Tuscan life by staying at agritourism properties, where you can enjoy local cuisine and wine.**

Top attractions in and around Cortona

Cortona, nestled in the heart of Tuscany, is a delightful destination perfect for a romantic getaway or outdoor adventure. Visitors can immerse themselves in the city's rich culture by exploring its stunning churches, charming piazzas, and fascinating museums. With its breathtaking scenery and vibrant city life, Cortona offers a unique blend of history and natural beauty, ensuring an unforgettable experience for all who wander through its ancient streets.

  • Villa Bramasole: A historic villa that embodies the charm of Cortona, Villa Bramasole offers a glimpse into the region's rich culture and history. Its serene surroundings and stunning architecture provide a picturesque backdrop for visitors seeking a tranquil experience.
  • Lake Trasimeno: Although located 18km from Cortona, Lake Trasimeno is a must-visit for its beautiful beaches and breathtaking scenery. Ideal for outdoor activities and romantic strolls, the lake's serene atmosphere is perfect for relaxation.
  • Piazza della Repubblica: The heart of Cortona, this vibrant piazza is surrounded by historical buildings and bustling cafés. It’s a cultural hub where you can immerse yourself in local life, enjoy artisan shops, and savour authentic Tuscan cuisine.

Things to do recommended for couples

In Cortona, savour a romantic evening dining al fresco at a quaint trattoria, followed by a leisurely walk through the charming cobblestone streets. Don’t miss the stunning sunset views from the Belvedere, creating the perfect backdrop for a memorable couple’s moment.

Things to do recommended for families

Families can explore the enchanting Etruscan Museum, marvel at the stunning views from the ancient hilltop, or enjoy a leisurely stroll through the charming streets filled with local shops and gelaterias. Don’t miss the chance to savour authentic Tuscan cuisine at family-friendly trattorias.

Things to do recommended for groups

Groups visiting Cortona can experience the thrill of motor racing at the Magione Racetrack and the Autodromo dell'Umbria, both located 26km away. These venues offer an adrenaline-fueled atmosphere perfect for adventure enthusiasts seeking excitement in Tuscany.

*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

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, be sure to apply the appropriate filters to meet your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cortona with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can apply filters for all these options and more on Vrbo.
  • Traveling to Cortona 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: For many families, a holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Cortona

Cortona, nestled in the stunning Tuscan hills, offers a captivating blend of history and romance. Stroll through its picturesque streets, where charming stone buildings and breathtaking views of the Italian countryside await. Experience local festivals that celebrate the town's rich culture and warm hospitality. Whether you're wandering the ancient walls or enjoying a leisurely meal at a quaint trattoria, Cortona promises an unforgettable escape filled with scenic beauty and a relaxed atmosphere.

  • Cortona Old Town: Nestled in the hills of Tuscany, Cortona Old Town is a charming neighbourhood known for its rich cultural heritage and stunning views. Visitors are drawn to its narrow cobblestone streets, historic architecture, and vibrant arts scene, perfect for a romantic getaway or cultural exploration. With attractions like the ancient Etruscan walls, the beautiful historic bridge, and local theatres offering performances, there’s plenty to engage the senses. Relaxation is also key here, with numerous spas available for those looking to unwind after a day of exploration.
  • Camucia: Just a stone's throw from Cortona, Camucia is a delightful village that combines local charm with modern conveniences. Ideal for a leisurely shopping experience, visitors can explore various shopping centres and enjoy the local theatre scene. Its proximity to scenic lakes and historic sites makes it a perfect spot for those seeking outdoor activities or romantic strolls. The blend of historical places and natural beauty creates a unique atmosphere that captures the essence of Tuscany.
  • Terontola: A quaint village located near Cortona, Terontola offers breathtaking scenery and a peaceful escape from the bustling tourist spots. Visitors can enjoy outdoor activities while taking in the picturesque landscape, including serene lakes and significant architecture. The local places of worship reflect the region's rich history and spiritual heritage, making it a perfect spot for contemplation and appreciation of Tuscany’s beauty. Whether you’re exploring the scenic surroundings or simply soaking in the tranquil atmosphere, Terontola is a hidden gem waiting to be discovered.

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 LowSlightly Low
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 SunnyAverageAverage
December41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage

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, opting for a longer stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The natural setting of Cortona is ready to explore

Come and experience Cortona and its cathedral, monuments and musicals. This city is well-known for its horse riding and museums. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Cortona

Are you looking for top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Cortona a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Magione Racetrack (16.2 mi / 26 km)
  • Cantina del Redi (16.2 mi / 26.1 km)
  • Consorzio del Vino Nobile di Montepulciano (16.3 mi / 26.2 km)
  • Terme di Chianciano (18.2 mi / 29.3 km)
  • Antognolla Golf (18.3 mi / 29.4 km)
  • Piscine Termali Theia (18.3 mi / 29.5 km)

Exploring the natural features in Cortona

Whether you're looking for adventure or just want to take in the scenery, Cortona is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Isola Maggiore (8.7 mi / 14 km)
  • Sualzo Beach (10.3 mi / 16.7 km)
  • Lake Trasimeno (11.5 mi / 18.4 km)
  • Piazza Guido Monaco (14.1 mi / 22.6 km)
  • Val di Chiana (15.7 mi / 25.2 km)
  • Terme di Montepulciano Spa (16.7 mi / 26.9 km)

Transport to and around Cortona

The nearest airport is in Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG), located 28.9 mi (46.4 km) from the city centre.

If you're travelling 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 holiday rental?
When considering a holiday rental in Cortona, Tuscany, a popular area to stay is the historic centre. This charming area boasts a rich tapestry of medieval architecture, narrow cobbled streets, and stunning views of the surrounding countryside. You'll find a variety of properties available, including quaint apartments and elegant villas, great for immersing yourself in the local culture.

In the historic centre, you can easily visit top attractions such as the beautiful Piazza della Repubblica, where you can enjoy a coffee while soaking in the vibrant setting. The nearby Diocesan Museum houses an impressive collection of religious art, offering a glimpse into the region's artistic heritage. Additionally, the scenic walks around the town provide breathtaking views, making it an ideal spot for those who appreciate both history and nature.

Another excellent option is the area surrounding the Etruscan walls, which not only offers a selection of lovely accommodations but also promises a peaceful retreat with easy access to the town's amenities. Staying here allows you to enjoy the tranquillity of the Tuscan hills while being just a short stroll away from the town's lively cafés and shops.
How much does it cost to rent a holiday home in Cortona?
Prices for holiday 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 holiday 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 holiday rental accomodation in Cortona?
In Cortona, villas are the most popular type of holiday rental, with around 1,352 available throughout the picturesque town and surrounding countryside. These spacious rooms typically feature multiple bedrooms, private gardens, and fully equipped kitchens, making them ideal for families or larger groups seeking a relaxing retreat in Tuscany. Additionally, there are approximately 1,152 apartments available, often located in charming neighbourhoods close to the town's historic centre, offering amenities such as comfortable living spaces and kitchen facilities. For those looking for a more rustic experience, about 720 holiday houses can be found, along with a few quaint cottages and chalets that provide a unique charm.
Are there any family house rentals in Cortona?
In Cortona, Tuscany, there are numerous family-friendly holiday rentals available, with around 505 options to choose from. This picturesque town is known for its charming atmosphere and stunning landscapes, making it an ideal spot for families. Many of the properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or relax.

Visitors can expect amenities such as Wi-Fi, air conditioning, and sometimes even private pools or gardens, which enhance the overall experience. The town itself is rich in history, with attractions like the Etruscan Museum and the beautiful Piazza della Repubblica nearby, providing plenty of opportunities for exploration.

Cortona's location in the heart of Tuscany also allows for easy day trips to nearby cities such as Arezzo and Montepulciano, adding to the family adventure.
Can I rent a holiday home with a pool or hot tub in Cortona?
In Cortona, Tuscany, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 566 options to choose from. This picturesque hilltop town offers a range of accommodations in its charming neighbourhoods, including the historic centre, where you can find villas with stunning views of the surrounding countryside. Many of these properties come equipped with private swimming pools, hot tubs, and spacious outdoor areas ideal for relaxation and enjoying the Tuscan sun.

Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even barbecue facilities for alfresco dining. Some rentals may also include additional luxuries like landscaped gardens and panoramic terraces, providing a great backdrop for a memorable holiday. Find your rental in Cortona with a pool or a hot tub.
Can I find long-stay holiday rentals in Cortona?
A long-stay holiday rental in Cortona 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.
Are there pet-friendly house rentals in Cortona?
In Cortona, Tuscany, there are numerous pet-friendly house rentals available, offering travellers a variety of options to choose from. Many of these holiday homes typically feature amenities such as spacious gardens, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups travelling with pets.

The charming historic centre of Cortona provides easy access to local shops, restaurants, and picturesque streets, great for leisurely strolls with your furry companions. Additionally, nearby attractions like the Parco Archeologico di Cortona and the surrounding countryside offer great opportunities for outdoor activities, including hiking and exploring the scenic landscapes of Tuscany.
Are there any remote work holiday rentals in Cortona?
In Cortona, Tuscany, there are numerous remote work holiday rentals available, with around 3,036 options to choose from. This charming town, known for its stunning views and rich history, offers a variety of accommodations that cater to those looking to work remotely while enjoying the beauty of the Italian countryside. Many properties come with essential amenities such as free Wi-Fi, both in-room and in public areas, ensuring a reliable internet connection for work-related tasks.

Travellers can expect comfortable living spaces that often include dedicated work areas, allowing for a productive environment. In addition to work-friendly amenities, many rentals also offer beautiful views of the surrounding hills and access to local attractions, such as the Etruscan Academy and the picturesque Piazza della Repubblica. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cortona holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cortona 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.
What are popular rental amenities in Cortona?
In Cortona, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals while enjoying the local flavours of Tuscany. Many of the holiday rentals also feature onsite parking, making it convenient for those travelling by car. A fireplace is often included, providing a cosy atmosphere, especially during the cooler months. Additionally, some properties welcome pets, making them an excellent choice for animal lovers. For those seeking relaxation, private pools are available in several rentals, offering a refreshing retreat amidst the stunning Tuscan landscape.
When is the best time to visit Cortona for a holiday rental?
April is a delightful time to visit Cortona, as the picturesque Tuscan landscape begins to bloom, creating a stunning backdrop for your holiday. This month offers mild temperatures, typically ranging from 10 to 20 degrees Celsius, making it ideal for exploring the charming streets and historic sites without the intense heat of summer. The town's vibrant setting is enhanced by fewer tourists, allowing for a more intimate experience as you discover local cafés and shops.

The peak season, spanning from July to September, sees Cortona bustling with visitors, drawn by the warm weather and numerous festivals. While this period is lively and full of energy, it can also mean larger crowds at popular attractions. However, if you enjoy the vibrant summer ambiance and don't mind sharing the space with fellow travellers, this is when you'll find the town in full swing, with outdoor dining and cultural events in abundance.

For those seeking a more budget-friendly option, consider visiting in January. This low season presents an opportunity to experience Cortona's winter charm, complete with quieter streets and the chance to enjoy the local cuisine in a relaxed atmosphere.

Ultimately, the best time to book a holiday rental in Cortona hinges on your preferences: April for a pleasant spring escape with fewer crowds, or the summer months for a lively experience filled with local festivities.
How early should I book a Cortona holiday rental?
Book your Cortona 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?
In Cortona, visitors can immerse themselves in a rich tapestry of history and culture. The town's historic centre is a must-see, featuring the stunning Piazza della Repubblica, where you can admire the beautiful Palazzo Comunale and the Etruscan Museum, showcasing artefacts from the region's ancient past.

For breathtaking views, head to the Basilica di Santa Margherita, perched atop a hill, offering panoramic vistas of the surrounding Tuscan landscape. Art enthusiasts will appreciate the Diocesan Museum, which houses works by renowned artists.

Exploring the winding cobblestone streets of Cortona, you'll find charming shops, cafés, and local trattorias serving authentic Tuscan cuisine.
Can I change or cancel my Cortona home rental booking on Vrbo?
To find Cortona 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 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 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.
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, 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.

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