Cortona holiday lettings

We found 3,181 holiday rentals — enter your dates for availability

Select from 276 houses, 349 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:6 Feb - 13 Feb

Image gallery for Villa Poggio del Sole, 8-10 Pax, Private Pool, Air Conditioned

Pool
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Villa Poggio del Sole, 8-10 Pax, Private Pool, Air Conditioned

Cortona, Provincia di Arezzo

9% off
Price is £3,991
for 7 nights, 1 villa
£570 per night
includes taxes & fees
Villa Poggio del Sole, 8-10 Pax, Private Pool, Air Conditioned

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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • Antognolla Golf (18.3 mi / 29.4 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 planning a holiday rental in Cortona, Tuscany, one of the best areas to consider is the historic centre. This charming neighbourhood is steeped in history and offers a plethora of attractions, including the stunning Piazza della Repubblica, where you can soak in the vibrant atmosphere, and the magnificent Diocesan Museum, which showcases beautiful artworks and artefacts. The cobbled streets are lined with delightful shops, cafes, and restaurants, making it a great spot for immersing yourself in local culture.

Another appealing option is the area surrounding the Basilica di Santa Margherita. This neighbourhood not only provides a serene environment with breathtaking views of the surrounding countryside but also allows easy access to the basilica itself, which is a significant pilgrimage site. Numerous holiday rentals are available here, offering both rustic charm and modern comforts, ensuring a pleasant stay.

For those who prefer a more tranquil setting, the outskirts of Cortona, particularly around the area of Fratticciola, provide an idyllic countryside experience. Here, you can enjoy the beauty of the Tuscan landscape while still being a short distance from the town centre. This area features several properties, often with gardens or terraces, great for relaxation after a day of exploration.
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 401 available throughout the charming Tuscan countryside. These properties typically feature spacious layouts, luxurious amenities, private gardens, and often stunning views of the surrounding hills. Many villas come equipped with fully fitted kitchens, swimming pools, and outdoor dining areas, making them ideal for families or groups seeking a relaxing getaway.

Apartments also attract a significant number of visitors, with about 306 options located within the historic centre and nearby areas. These apartments usually offer a mix of modern comforts and traditional Tuscan charm, featuring fully equipped kitchens and cosy living spaces.

For those seeking more unique accommodations, there are approximately 232 holiday houses available, which provide a homely atmosphere and often come with outdoor spaces for enjoying the beautiful Tuscan weather. Cottages, though fewer in number at around 16, provide a rustic experience, while several chalets are scattered across the area, suiting those looking for a quaint retreat.
Are there any family house rentals in Cortona?
In Cortona, Tuscany, there is a fantastic selection of family-friendly house rentals, with around 538 options available. This charming hilltop town, known for its stunning views and rich history, offers homes in various neighbourhoods, such as the historic centre and the surrounding countryside. Many properties feature spacious living areas great for family gatherings, fully equipped kitchens for preparing delicious Italian meals, and outdoor spaces where children can play and adults can relax.

Visitors will appreciate the close proximity to cultural attractions like the Etruscan Academy Museum and the beautiful Piazza della Repubblica, where local markets and cafes thrive. Additionally, some rentals may include amenities such as private gardens, swimming pools, and barbecue areas, enhancing the overall experience.
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 approximately 683 options to choose from. This charming town, known for its stunning views and rich history, offers a variety of properties located in the picturesque countryside and within the historic centre. Many rentals come with private pools, hot tubs, and beautifully landscaped gardens, ideal for relaxation after a day of exploring. 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, with over 500 properties suiting travellers with pets. Many of these holiday homes are situated in scenic locations, offering breathtaking views of the surrounding countryside and the iconic Tuscan hills. Travellers can expect a variety of amenities, including spacious outdoor areas, private gardens, and terraces where pets can enjoy the open air. Inside, these rentals often feature fully equipped kitchens, comfortable living spaces, and sometimes even fireplaces, providing a warm and friendly space for both guests and their furry companions. See all pet-friendly rentals in Cortona.
Are there any remote work holiday rentals in Cortona?
In Cortona, Tuscany, there is an abundance of remote work-friendly holiday rentals available, with around 862 options to choose from. This picturesque town, known for its stunning views and rich history, provides an ideal setting for those looking to balance work and leisure. Many properties come equipped with essential amenities tailored for remote work, including high-speed Wi-Fi, dedicated office spaces, and comfortable desk chairs. Some even feature business centres and meeting rooms, accommodating those who may need to conduct meetings or focus on projects without distractions. 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 holiday rental amenities include kitchens, refrigerators, and free Wi-Fi, making it convenient for guests to prepare their own meals and stay connected. Many properties also feature private pools, offering a luxurious way to relax and enjoy the beautiful Tuscan weather. These amenities enhance the home-like experience that travellers seek while exploring the charming streets and cultural landmarks of Cortona.
When is the best time to visit Cortona for a holiday rental?
April is the most popular time to visit Cortona, as the spring season brings mild weather and a vibrant atmosphere to this charming Tuscan town. During this month, visitors can enjoy comfortable temperatures averaging around 15°C, superb for leisurely strolls through the picturesque streets and exploring the stunning countryside. The blooming flowers and lush landscapes create an ideal setting for outdoor activities, including hiking and cycling, allowing you to fully immerse yourself in the breathtaking beauty of the region.

The peak tourist season in Cortona runs from July to September, when the town buzzes with activity. This time is particularly appealing for those who enjoy cultural events, as numerous festivals and local markets take place, showcasing the rich traditions of Tuscany. However, if you're looking for a more tranquil experience, visiting in April offers a delightful balance between pleasant weather and fewer crowds, making it easier to explore popular attractions like the Etruscan Academy Museum and the lovely Piazza della Repubblica.

For travellers seeking to save a bit on their holiday rental, consider planning your trip in January. While this is the low season, it provides a unique opportunity to experience Cortona in a quieter, more intimate setting. The winter months reveal the town's charm in a different light, with fewer tourists and the chance to enjoy local cuisine in a cosy atmosphere.
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 take part in a rich tapestry of history and culture. The town's historic centre is a treasure trove, featuring the stunning Piazza della Repubblica, where one can admire the beautiful Town Hall and the Palazzo Comunale. Nearby, the Diocesan Museum showcases a remarkable collection of religious art, making it a must-visit for art enthusiasts.

For those interested in architecture, the Basilica di Santa Margherita, perched atop a hill, offers breathtaking views of the surrounding countryside and is an excellent spot for photography. The charming streets of Cortona are lined with local shops and eateries, offering authentic Tuscan cuisine and regional wines.
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 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 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.

More holiday ideas