Cortona holiday lettings

We found 3,104 holiday rentals — enter your dates for availability

Select from 145 houses, 179 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:12 Jun - 19 Jun

Image gallery for Apartment in Farmhouse

Property grounds
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
Price is £822
for 7 nights, 1 room
£117 per night
includes taxes & fees
Apartment in Farmhouse

Find spaces that suit your style

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Why visit Cortona

  • Charming hilltop town: Cortona offers picturesque streets and stunning vistas, perfect for romantic strolls.
  • Cultural experiences: Explore historical churches, vibrant piazzas, and fascinating museums that showcase the town's rich heritage.
  • Outdoor activities: The surrounding countryside invites hiking, cycling, and other outdoor excursions, ideal for nature lovers.
  • Delightful accommodation: Choose from a variety of charming villas, private homes, and apartments for a memorable stay.
  • Welcoming atmosphere: Enjoy the friendly locals and authentic Italian hospitality that enhances your travel experience.

Popular types of accommodation in Cortona

At Cortona holiday rentals, we offer a delightful selection of accommodation options tailored to your needs. Whether you're seeking the charm of the best villas in Cortona, the comfort of houses, or the convenience of apartments, we have something for everyone. Explore our Cortona villa rentals for a truly memorable stay, ensuring transparency, savings, and reassurance for your trip. Discover the perfect base for your adventures in this stunning Tuscan town!

  • Villas: The most sought-after option for holiday stays in Cortona, offering spacious living and stunning views.
  • Houses: A popular choice for families and groups, providing a homely atmosphere and privacy.
  • Apartments: Ideal for couples or solo travellers, these self-contained units are conveniently located.
  • Cottages: Charming and quaint, perfect for a cosy retreat in the Tuscan countryside.
  • Agritourism: Experience authentic Italian rural life with farm stays that offer local produce and traditions.**

Top attractions in and around Cortona

Cortona offers a delightful blend of outdoor activities, romantic settings, and cultural experiences, making it ideal for a memorable vacation. Visitors can explore the charming churches, vibrant piazzas, and fascinating museums both within the town and in the surrounding area, catering to those seeking culture and outdoor adventures. Whether you're wandering through quaint streets or enjoying the scenic beauty, Cortona promises an enriching experience for every traveller.

  • Lake Trasimeno: Situated 6.8km from Cortona, this picturesque lake offers stunning scenery and serene beaches, perfect for outdoor activities and romantic strolls. Enjoy its tranquil atmosphere while taking in the natural beauty.
  • Villa Bramasole: Nestled within Cortona, this historic villa is steeped in culture and charm. Its beautiful architecture and surrounding gardens provide a glimpse into the region's rich history and artistic heritage.
  • Piazza della Repubblica: Located in the heart of Cortona, this vibrant square is a cultural hub bustling with life. Enjoy local cafés, shops, and the stunning architecture that reflects the town's storied past.

Things to do recommended for couples

For a romantic getaway in Cortona, indulge in luxury at the Tennis Club Castiglionese, explore the enchanting Agricola Buccelletti Winery, or enjoy the outdoor charm of Fattoria Le Capezzine. Each offers a delightful experience perfect for couples seeking romance and entertainment.

Things to do recommended for families

Families can explore the charming streets of Cortona, visit the Etruscan Academy Museum, or enjoy a picnic in the scenic Parterre Park. Don't miss the chance to take a cooking class together, where everyone can learn to make traditional Tuscan dishes.

Things to do recommended for groups

Groups visiting Cortona can indulge in shopping at the Valdichiana Outlet Village, enjoy a cultural evening at the Signorelli Theatre, and embark on an adventurous hike along Hannibal's Journey for breathtaking scenery.

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

Whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cortona with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Cortona with young kids: Journeying with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with ensuring that amenities are suitable for their age, 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: For many, a family 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 to ensure 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 spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a lovely kitchen, or a private pool in your search criteria as well.

Where to stay in and around Cortona

Cortona, a charming hilltop town in Tuscany, offers an unforgettable experience for those seeking romance and culture. With its welcoming atmosphere and rich history, you can explore the centre of Cortona, where delightful cafes and historical sites await. Just minutes away, the surrounding countryside beckons for outdoor excursions, making it a perfect base to discover nearby gems. Whether you’re wandering cobbled streets or enjoying scenic vistas, Cortona promises a memorable Italian getaway.

  • Cortona Old Town: Perched on a hilltop, Cortona Old Town is a charming and historic neighbourhood that captivates visitors with its narrow, cobbled streets and stunning vistas of the surrounding Tuscan countryside. As a cultural gem, it offers a romantic atmosphere perfect for leisurely strolls, boutique shopping, and indulging in local cuisine at quaint trattorias. Notable attractions include the Etruscan Academy Museum and the picturesque Piazza della Repubblica. For those seeking relaxation, a visit to a local spa or enjoying a performance at the historic theatre adds to the enriching experience.
  • Tuoro sul Trasimeno: Located a mere 3.7km from Cortona, Tuoro sul Trasimeno is a delightful lakeside town renowned for its scenic beauty and outdoor activities. Nestled on the shores of Lake Trasimeno, it offers a serene escape for couples and nature enthusiasts alike. Visitors can enjoy hiking trails with breathtaking views, or unwind with spa treatments that take advantage of the area's natural hot springs. The town is rich in history, with nearby landmarks such as the ancient Roman ruins and the picturesque islands on the lake that invite exploration.
  • Castiglion Fiorentino: Situated just 3.7km from Cortona, Castiglion Fiorentino boasts a blend of outdoor adventure and rich cultural heritage. This charming city is ideal for romantic getaways, featuring scenic walks through its historic centre and breathtaking countryside views. Visitors can indulge in body treatments at local spas or enjoy activities at private country clubs. Key attractions include the ancient castle ruins, the historic bridge, and the serene nearby lake, making it a perfect spot for those seeking both relaxation and exploration.

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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new getaways, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved or booked, now neatly organised under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply 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:

  • Fattoria Le Capezzine (7.5 mi / 12 km)
  • Magione Racetrack (16.2 mi / 26 km)
  • Cantina del Redi (16.2 mi / 26.1 km)
  • Cantina Contucci (16.3 mi / 26.2 km)
  • Consorzio del Vino Nobile di Montepulciano (16.3 mi / 26.2 km)
  • Terme di Chianciano (18.2 mi / 29.3 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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