Cortona holiday rentals

We found 2,879 holiday rentals — enter your dates for availability
Select from 147 houses, 193 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:9 Oct - 16 Oct

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Why visit Cortona

  • Historic Charm: Cortona captivates visitors with its ancient churches, intriguing museums, and centuries-old landmarks.
  • Pictorial Views: Enjoy sweeping vistas from this hilltop town, where every glance reveals a slice of Tuscan splendour.
  • Winding Streets: The maze of charming alleys invites leisurely exploration, offering hidden treasures at every turn.
  • Cultural Richness: Immerse in a blend of art, history, and local traditions that make Cortona a veritable cultural hub.
  • Scenic Outdoors: Experience the perfect balance of urban and rural beauty, ideal for romantic strolls and quiet reflection.

Popular types of accommodation in Cortona

Discover Cortona, Tuscany – a captivating city steeped in history, art, and culture. Explore its enchanting landmarks, vibrant local markets, and scenic views. Whether you're seeking a villa, private holiday home, or apartment, find the perfect cortona holiday rentals to suit your style. Enjoy unique holiday rentals in this picturesque destination, where every corner tells a story.

  • Villas: Elegant and spacious residences offering luxurious amenities and stunning views, ideal for a lavish getaway.
  • Private Holiday Homes: Comfortable and inviting properties that provide a homely atmosphere, perfect for families or groups.
  • Apartments: Conveniently located living spaces that offer a blend of comfort and accessibility, suitable for couples or solo travellers.
  • Cottages: Charming and quaint accommodations nestled in picturesque surroundings, ideal for a peaceful retreat.
  • Agritourism: Unique stays on working farms that offer an authentic taste of rural life and local produce.**

Top attractions in and around Cortona

Cortona, nestled in the heart of Tuscany, offers a romantic escape with its stunning scenery and rich culture. Visitors can explore charming piazzas, historic churches, and captivating museums that showcase the city's artistic heritage. Whether wandering through the winding streets or enjoying breathtaking views from its hilltop location, Cortona provides a perfect blend of outdoor adventure and cultural experiences, making it an ideal destination for couples and travellers seeking a picturesque Italian getaway.

  • Villa Bramasole: A historic bridge immersed in Cortona’s rich cultural ambience, offering splendid architectural details and an evocative atmosphere.
  • Lake Trasimeno: A picturesque lake 18km from Cortona, celebrated for its scenic beauty, outdoor leisure, and romantic allure.
  • Eremo Le Celle: An atmospheric church within Cortona, exuding cultural heritage and spiritual charm.

Things to do recommended for couples

For a romantic getaway in Cortona, savour a candlelit dinner at a charming trattoria, explore the picturesque streets hand-in-hand, and enjoy a sunset picnic overlooking the stunning Tuscan countryside. Don't miss the enchanting views from the ancient fortress for a truly memorable experience together.

Things to do recommended for families

Experience authentic Tuscan life in Cortona with family-friendly activities, including delightful local food markets, charming artisan workshops, and scenic nature walks, perfect for exploring the region's rich history and culture.

Things to do recommended for groups

Experience the thrill of motor racing at Magione Racetrack and Autodromo dell'Umbria, both located 26km from Cortona. Enjoy the adrenaline rush with your group in these vibrant, adventure-filled venues.

*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 travelling with a group, family, pets, or seeking extended stays, be sure to prioritise your filters accordingly. Here are some helpful Stayz booking tips for you.

  • Traveling to Cortona with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all these options and more on Stayz.
  • Traveling to Cortona with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Cortona: Some travellers believe that a family holiday is incomplete without the company of their four-legged companion. If you share this sentiment, consider exploring Stayz properties that welcome pets. Many of these accommodations offer amenities such as feeding bowls and beds, ensuring that every member of the family feels at ease.
  • 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 secure savings on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Cortona

Cortona offers a delightful blend of history and romance. Wander its charming streets, explore ancient landmarks, and enjoy scenic outdoor vistas. This small town in Tuscany is perfect for a pleasant holiday, inviting you to discover its relaxed atmosphere and rich heritage. A trip to Cortona promises a memorable experience, where every corner tells a story of timeless beauty and warm, friendly locals.

  • Cortona Old Town: Nestled in the heart of Cortona, this historic neighbourhood offers a vibrant cultural tapestry and a romantic ambience. A blend of tradition and modernity, visitors can enjoy a diverse range of entertainment options from theatres to spas, and even a golf course. The area boasts significant landmarks such as historic sites and bridges, including an ancient structure that has stood the test of time, making it a captivating destination for those seeking both culture and history.
  • Camucia: This charming village in the Cortona region offers a unique mix of cultural and outdoor experiences. Known for its romantic setting, Camucia is surrounded by historic sites and a picturesque lake, alongside a renowned historic bridge. Travellers can explore local shopping centres and enjoy performances at the theatre, all while taking in the scenic beauty and heritage of the area.
  • Terontola: Set within the enchanting landscape of Cortona, Terontola is a village that invites outdoor enthusiasts and those looking for a romantic getaway. The area is celebrated for its breathtaking scenery, with landmarks including a serene lake, notable architectural marvels, and a revered place of worship. Its tranquil environment and scenic vistas offer a refreshing retreat for visitors seeking a blend of nature and culture.

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 Stayz is a breeze

Looking to save on your upcoming journey? Being flexible with your travel dates can prove beneficial, as prices frequently fluctuate. You could also secure considerable savings by opting for an extended stay. To discover a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a straightforward space to create new journeys, resume planning from where you last stopped, or review and arrange your itineraries. Here you can find properties you have either saved or booked, neatly categorised as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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)
  • Cantina del Redi (16.2 mi / 26.1 km)
  • Cantina Contucci (16.3 mi / 26.2 km)
  • Wine Tasting al Fontanaro (18 mi / 28.9 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)
  • 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)
  • Terme Sant'Elena (17.2 mi / 27.7 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, Stayz 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 Stayz 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 Stayz. 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 Stayz, 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, Stayz 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, Stayz 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, Stayz'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 Stayz 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 Stayz. 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 Stayz, 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 Stayz'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.