Cortona holiday homes

We found 3,025 holiday rentals — enter your dates for availability

Select from 280 houses, 355 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 Dec - 19 Dec
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Why visit Cortona

  • Stunning Views: Enjoy breathtaking panoramas of the Tuscan countryside from various vantage points in Cortona.
  • Rich History: Explore the iconic Cortona Cathedral and the town's fascinating museums showcasing its historical allure.
  • Charming Streets: Wander through picturesque streets filled with vibrant piazzas, quaint shops, and delightful cafés.
  • Outdoor Adventures: Engage in numerous outdoor activities that highlight the stunning landscapes surrounding Cortona.
  • Warm Hospitality: Experience the friendly locals who enhance your visit with their welcoming nature and rich culture.

Top attractions in and around Cortona

Cortona is a delightful destination for outdoor enthusiasts and culture lovers alike, offering a romantic atmosphere perfect for any type of traveller. Explore its stunning churches, vibrant piazzas, and fascinating museums. Don't miss the iconic Cortona Cathedral and enjoy breathtaking views of the surrounding countryside. With nearby attractions and various activities available, your visit to Cortona promises to be an unforgettable experience filled with charm and history.

  • Lake Trasimeno: Just 17.7km from Cortona, this stunning lake offers beautiful beaches and scenic views. Perfect for outdoor activities and romantic picnics, it's a tranquil spot to unwind and soak in the natural beauty of Tuscany.
  • Villa Bramasole: Nestled in Cortona, this historic villa is rich in culture and charm. Its stunning architecture and beautiful surroundings provide a glimpse into the area's artistic heritage, making it a must-visit for history buffs.
  • Cortona Cathedral: Located in the heart of Cortona, this magnificent cathedral showcases exquisite architecture and rich cultural significance. It's an ideal place for quiet reflection and appreciation of local artistry.

Things to do recommended for couples

Planning a romantic getaway in Cortona? Indulge in relaxation at Terme di Chianciano spa, only 29.0km away. Enjoy luxury at Tennis Club Castiglionese, just 8.0km away, or savour the charm of Agricola Buccelletti Winery, also 8.0km away, for a delightful wine experience.

Things to do recommended for families

Families will love exploring Cortona's charming streets, visiting the Etruscan Museum, or enjoying a picnic at Parterre Park. Don't miss the local markets where kids can sample delicious gelato and fresh produce, making for a delightful family day out in this beautiful Tuscan town.

Things to do recommended for groups

Explore the Valdichiana Outlet Village for a unique shopping experience, enjoy a show at the charming Signorelli Theatre, or embark on Hannibal's Journey for a stunning hike through the countryside. Each activity offers a perfect blend of culture, adventure, and fun for your group.

*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 heading off with a group, enjoying a family getaway, bringing along your pets, or planning an extended stay, be sure to apply the right filters to match your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cortona with a group: Think about how many bedrooms you'll require, along with features like a full 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: Travelling with young kids can be a bit tricky. 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 family-friendly attractions.
  • Taking your pets with you to Cortona: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with 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 with discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Cortona

Cortona, nestled in the heart of Tuscany, offers a perfect blend of outdoor adventures and rich culture for your holiday. Wander through its charming streets, soak in the romantic atmosphere, and explore nearby gems that showcase the region's historical allure. Whether you're after a family getaway or a peaceful farm holiday, Cortona and its surrounding areas promise friendly locals and unforgettable experiences amidst stunning landscapes.

  • Cortona Old Town: Nestled in the heart of Tuscany, Cortona Old Town is a charming neighborhood that brims with history and culture. Visitors are drawn to its cobblestone streets, where ancient architecture meets stunning views of the surrounding hills. Enjoy a romantic stroll, visit the local theatre for a performance, or unwind at a nearby spa. Notable landmarks include the historic fortress and scenic lakes, making it a perfect spot for both outdoor adventures and cultural exploration.
  • Camucia: Just a short distance from Cortona, Camucia is a quaint village that offers a relaxed atmosphere for those seeking a blend of culture and outdoor experiences. The village boasts beautiful historic bridges and sites that tell the tale of its rich heritage. Outdoor enthusiasts can enjoy golfing or take in the scenic countryside views, while romantic evenings can be spent at the local theatre, showcasing the vibrant community life. Camucia is a delightful stop for those wanting to experience authentic Tuscan charm.
  • Castiglion Fiorentino: Located a mere 9.7km from Cortona, Castiglion Fiorentino is a picturesque city that captivates visitors with its stunning landscapes and cultural offerings. Explore the serene surroundings, including tranquil lakes and historic bridges, perfect for a leisurely day out. This city is ideal for outdoor pursuits, whether you're indulging in spa treatments or enjoying a round at a country private club. The blend of history and natural beauty makes Castiglion Fiorentino a must-visit for any traveler in the region.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.2°F (4.0°C)Light RainMostly CloudySlightly Low
February41.2°F (5.1°C)Light RainMostly SunnySlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverage
April52.7°F (11.5°C)Light RainMostly SunnySlightly High
May59.5°F (15.3°C)Light RainMostly SunnyAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverage
July74.8°F (23.8°C)No Rain (Dry)SunnySlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnySlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverage
December41.7°F (5.4°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Are you keen to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient way to plan your getaways, manage your reservations, and keep everything in order. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To start exploring your Trip Boards, head over to: https://www.bookabach.co.nz/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 home accommodation in Cortona?
Apartments are the most popular style of holiday home in Cortona, according to our data. Even if you've got a different idea in mind, Bookabach 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 home in Cortona?
The average price for a holiday home 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 Bookabach 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 homes in Cortona?
There are, yes. Take your pick of 474 holiday homes that allow pets in Cortona on Bookabach. Our furry friends need to get away from it all too, so simply use our search function for pet-friendly holiday homes 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 Bookabach, then use the "pool" filter to find a place to make a splash!
What are popular home amenities in Cortona?
Some of the most popular home 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, Bookabach holiday properties feature the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday homes 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, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes 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 homes in Cortona?
Yes, you can take your pick from 126 one-bedroom homes in Cortona. Whether you'd like a secluded cottage or a cabin, Bookabach's one-bedroom homes 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 homes 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 homes 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 Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Cortona?
Decide on your travel dates and then use our filters to look for holiday homes with ac in Cortona on Bookabach. 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 home in Cortona?
The age limit can vary across properties on Bookabach, 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 home 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 Bookabach'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.

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