Cortona holiday lettings

We found 3,292 holiday rentals — enter your dates for availability

Select from 285 houses, 357 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:10 Oct - 17 Oct
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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.

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.

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

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.

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:

  • Arezzo Equestrian Centre (12.9 mi / 20.8 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 most popular type of holiday rental accommodation in Cortona?
Apartments are the most popular style of holiday rental in Cortona, according to our data. Even if you've got a different idea in mind, Vrbo has holiday homes in loads of sizes and shapes. Browse our options to find your perfect pad.
How much does it cost to rent a holiday rental in Cortona?
The average price for a holiday rental in Cortona is based on several factors, such as season, property type and length of stay. Whether you'd like a sprawling villa with room to move around or a cosy cabin for you and your other half, just enter your travel dates to discover stays with terrific value.
How much does it cost to rent a beach house in Cortona?
Prices for beach houses in Cortona may vary depending on the size and type of the property and time of year you're travelling. Just enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use our filters to tailor your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Cortona?
There are, yes. Take your pick of 474 holiday homes that allow pets in Cortona on Vrbo. Our furry friends need to get away from it all too, so simply use our search function for pet-friendly holiday rentals to find a property where your pup can lap up the good times.
Can I rent a house with a pool in Cortona?
Dig out your swimsuit and inflatable lounger, because there are 284 houses with a private pool in Cortona. Make a booking at one of these terrific holiday homes and make every day a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find a place to make a splash!
What are popular rental amenities in Cortona?
Some of the most popular rental amenities people are looking for in Cortona include an ocean view, a lake view and mountain views. Whether you're travelling with your besties, family or even pets, Vrbo holiday properties feature the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday rentals in Cortona?
With 87 properties that can host 10 or more guests in Cortona, there's no need to hold back on your invites. From fun family get-togethers to special events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.
Are there holiday rentals in Cortona that welcome kids?
Cortona has 470 family-friendly holiday homes. And finding a stay that welcomes kids is super easy with our "Properties good for families" filter. As well as having the entire place to yourselves, you'll also get amenities and perks like living rooms, private pools and yards.
What are the top attractions for families in Cortona?
Keep the kids amused at these fabulous family-friendly attractions in Cortona:

  • Palazzo Comunale
  • Casali Palace
  • Museum of the Etruscan Academy

Are there one-bedroom holiday rentals in Cortona?
Yes, you can take your pick from 126 one-bedroom rentals in Cortona. Whether you'd like a secluded cottage or a cabin, Vrbo's one-bedroom rentals are perfect if you don't require huge amounts of space. One of the major perks of having your own place? You won't ever have to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Cortona?
Select from 145 two-bedroom holiday properties in Cortona. Put your little ones in the second room or maybe fill it with a couple of your nearest and dearest friends. There's plenty of space for whoever's fortunate enough to be coming along.
Are there holiday rentals with WiFi in Cortona?
Whether you'd like to keep up with the latest news, check emails or post a pic to social media, there are 230 holiday homes with WiFi in Cortona. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Cortona?
Decide on your travel dates and then use our filters to look for holiday rentals with ac in Cortona on Vrbo. With 316 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Cortona?
The age limit can vary across properties on Vrbo, so be sure to look at the rules of the holiday home in Cortona you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Cortona for?
It's up to the Cortona property. To view all available options offering extended stays, simply type your dates and number of people into Vrbo's search page. You can look forward to having the whole place to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and a yard to play in. Keep your eyes open for long-term stays that offer weekly or monthly discounts.