Cortona vacation rentals

We found 3,054 vacation rentals — enter your dates for availability

Welcome to the enchanting Cortona, where the breathtaking Tuscan countryside unfolds around you, inviting romantic strolls and leisurely explorations. Wander through charming streets lined with historic churches and vibrant piazzas, or immerse yourself in local culture at the iconic Villa Bramasole. With diverse accommodations ranging from luxurious villas to cozy apartments, families and groups can enjoy the comfort and convenience of a home-away-from-home, all while soaking in the beauty of this captivating destination.

Holiday rentals with weekly discounts - Cortona

Showing deals for:Dec 11 - Dec 18

Exterior
Exterior
Lunch on the rear patio.
The Casa Castagni  living room
Exceptional
(5 reviews)

Gorgeously restored tranquil farmhouse

Castiglione del Lago

18% off
$212
$1,487 for 7 nights
All fees included
Gorgeously restored tranquil farmhouse
Dining
Outdoor dining
Pool
Exterior detail
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
$155
$1,086 for 7 nights
All fees included
Apartment in Farmhouse
Pool
Property grounds
Outdoor dining
Interior
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
$740
$5,181 for 7 nights
All fees included
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Private kitchen
Exterior
Outdoor dining
Living area
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
$255
$1,786 for 7 nights
All fees included
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Take a seat. You're finally home.
There's no doubt you're in Tuscany
Welcome to a piece of history!
The master bedroom promises privacy
Exceptional
(24 reviews)

Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

Castiglion Fiorentino

9% off
$160
$1,123 for 7 nights
All fees included
Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities
AHHH!  Tuscany!
Interior
Enter here
Relax in this cozy living area
Exceptional
(11 reviews)

❤️ of Castiglion Fiorentino

Castiglion Fiorentino

8% off
$121
$849 for 7 nights
All fees included
❤️ of Castiglion Fiorentino
entrance
View from the outside
Dining Room
Living room + Sofa bed
Exceptional
(58 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

14% off
$249
$1,742 for 7 nights
All fees included
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Living area
Exterior detail
Pool
Exterior
Exceptional
(14 reviews)

Ray's House - GLICINE Apartment

Passignano sul Trasimeno

8% off
$176
$1,229 for 7 nights
All fees included
Ray's House - GLICINE Apartment
Private kitchen
Outdoor dining
Room
Living area
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

8% off
$314
$2,196 for 7 nights
All fees included
Magnificent and Bright 2 BR Apt. with Terrace
Kitchen
Kitchen with View.
Bedroom2
Kitchen
Exceptional
(12 reviews)

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Montepulciano

23% off
$152
$1,064 for 7 nights
All fees included
Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
Pool
Outdoor dining
Exterior
Dining
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
$259
$1,810 for 7 nights
All fees included
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
Classic Apt. in a Palazzo with modern comforts and classic features
Gorgeous View to wake up to in the mornings!
Room
Interior
Exceptional
(36 reviews)

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Montepulciano

13% off
$395
$2,764 for 7 nights
All fees included
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
  • Peace of mind

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    Enjoy full kitchens, laundry, pools, yards and more
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    Learn more

Find out more about Cortona

Why visit Cortona

  • Stunning Scenery: Enjoy breathtaking views of the Tuscan countryside that surround Cortona, perfect for romantic walks.
  • Historic Architecture: Explore charming churches, lively piazzas, and historic palaces reflecting the city's rich heritage.
  • Villas and Culture: Discover beautiful villas nearby and immerse yourself in the local culture and traditions.
  • Quaint Streets: Wander through picturesque streets where each corner offers scenic views and delightful surprises.
  • Diverse Accommodations: Choose from luxury villas, cozy apartments, or charming vacation homes for a comfortable stay.

Popular types of accommodation in Cortona

If you're wondering about the best accommodations in Cortona, you're in the right place. Our most popular vacation rentals include charming villas, houses, and cozy apartments. Whether you’re searching for luxury villa rentals or comfortable villa rentals in Cortona, we have a variety of options to meet your needs. Discover the perfect getaway that combines stunning scenery with the comfort of home.

  • Villas: Luxurious and spacious, villas are the top choice for travelers seeking comfort and stunning views in Cortona.
  • Houses: These charming homes offer a cozy and personalized experience, perfect for families or groups.
  • Apartments: Ideal for those wanting convenience, apartments provide a home-like atmosphere in the heart of Cortona.
  • Cottages: Quaint and inviting, cottages offer a rustic charm for a peaceful getaway.
  • Agritourism: Experience rural life by staying on a working farm, enjoying fresh produce and authentic local culture.**

Top attractions in and around Cortona

Cortona, Tuscany is perfect for a romantic outdoor getaway, offering stunning scenery and rich culture. Explore charming churches, lively piazzas, and historic palaces that reflect the city's heritage. Nearby, you can discover beautiful villas and immerse yourself in the local culture. Whether you're seeking a city experience or outdoor adventures, Cortona has something to captivate every traveler.

  • Villa Bramasole: A historic villa with rich cultural significance, Villa Bramasole offers a glimpse into the elegant past of Cortona. Its stunning architecture and beautiful gardens create a serene environment, perfect for soaking in Tuscan charm.
  • Lake Trasimeno: Located 11 miles from Cortona, this picturesque lake is ideal for outdoor activities, romantic strolls, and scenic views. Enjoy a day at the beach or take a boat ride to explore its tranquil waters.
  • Piazza della Repubblica: Situated in the heart of Cortona, this vibrant square is a cultural hub, lined with charming cafes and shops. It's a great spot to relax and immerse yourself in the local atmosphere.

Things to do recommended for couples

For a romantic getaway in Cortona, consider visiting the Tennis Club Castiglionese, just 5 miles away. This private country club offers a luxurious atmosphere, perfect for couples looking to unwind and enjoy some quality time together amidst stunning Tuscan scenery.

Things to do recommended for families

Families visiting Cortona can explore the charming streets lined with shops and cafes, enjoy a picnic at Parco delle Stelle, and take a fun cooking class together to learn authentic Tuscan cuisine. Don't miss the beautiful views from the nearby hilltop.

Things to do recommended for groups

Explore the charming streets of Cortona with a guided walking tour, savor local wines at a vineyard tasting, or enjoy a cooking class where your group can create traditional Tuscan dishes together. Don't miss the breathtaking views from the hilltop Etruscan ruins.

*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 traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cortona with a group: Think about how many bedrooms you require, along with specific features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Cortona with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with providing 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 families, a vacation wouldn't be the same without their furry companion. If this resonates with you, explore 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 searching for vacation rentals with 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Cortona

Discover the enchanting charm of Cortona, a picturesque town in Tuscany, perfect for romantic getaways and outdoor adventures. Explore beautiful villas dotting the Italian countryside, and immerse yourself in the friendly atmosphere of this historic city. Enjoy leisurely strolls through its quaint streets, where every corner reveals scenic views and a rich cultural heritage. Cortona offers a delightful blend of relaxation and exploration, making it an ideal destination for your Italian vacation.

  • Tuoro sul Trasimeno: Located approximately 6 miles from Cortona, Tuoro sul Trasimeno is a charming town nestled by the picturesque Lake Trasimeno. This destination draws travelers seeking outdoor adventures and romantic getaways. With scenic hiking trails and serene beaches, it's perfect for nature lovers. The area is also known for its relaxing spas and educational venues, making it a great spot for a rejuvenating retreat. Notable attractions include the stunning lake views and nearby hot springs, providing a tranquil atmosphere to unwind and connect with nature.
  • Cortona Old Town: The historic heart of Cortona, Cortona Old Town is a captivating neighborhood brimming with culture and charm. Visitors are enchanted by its rich history and vibrant entertainment options. Explore the quaint streets lined with shops, theaters, and inviting spas. The area boasts significant landmarks like ancient bridges and historic sites, perfect for those interested in art and architecture. This romantic setting offers a delightful blend of culture and leisure, making it an ideal destination for couples and history buffs alike.
  • Castiglion Fiorentino: Just 6 miles from Cortona, Castiglion Fiorentino offers a delightful mix of outdoor activities and cultural experiences. This charming city is famed for its stunning landscapes and historic sites, making it a must-visit for travelers seeking both adventure and relaxation. Enjoy leisurely strolls through its scenic parks or indulge in some retail therapy at local shopping centers. With the presence of country clubs and inviting spas, Castiglion Fiorentino is perfect for a romantic escape or a family-friendly outing. Key attractions include its historic places, lakeside views, and impressive monuments.

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

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay to enjoy some substantial savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a dedicated area for you to plan new trips, manage your existing plans, and review your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Medieval magic in Cortona

Tucked in the southern region of Tuscany, Cortona dazzles with its ancient stone walls, medieval architecture and spectacular views from its prime hilltop location. Cortona vacation rentals provide an excellent base for exploring exquisitely preserved religious sites, tasting the spectacular wines of the region or taking a class on traditional Tuscan cuisine. There are museums to inspire, with the fascinating history of the many cultures that have thrived in Cortona, and, at the end of the day, you can watch the sunset over surrounding hills, as you sip wine and watch people from a comfortable seat in a piazza.

A hilltop fortress in Cortona

Housed in a gorgeous 13th-century palazzo, the Museo dell'Accademia Etrusca e della Città di Cortona is a riveting museum, filled with Roman and Etruscan treasures unearthed from the surrounding area. For staggeringly beautiful views of Tuscany and Umbria, the Medici fortress, Fortezza del Girifalco, cannot be beaten. Once you've soaked up the view, you can stay for a falconry show or dinner concert. The Eremo Francescano Le Celle, a Franciscan hermitage, is a short drive from Cortona vacation rentals. Nestled in the woods across an old stone bridge, it's a place of stillness broken only by the toll of bells.

History and art in Cortona

Lovers of history will find myriad delights in the medieval city of Cortona. The old walls of Cortona hold a wealth of stories, with a history incorporating the ancient Etruscans, the Romans, the powerful Medici family and Francis of Assisi, Cortona vacation rentals are within walking distance of many of Cortona's most important sites. Art lovers will find much to inspire in museums and galleries, while shoppers can wander the narrow streets to find treasures of local wines, produce and crafts. For a break from the heat, take a refreshing dip in the waters of nearby Lake Trasimeno.

Springtime beauty in Cortona

If you want to explore the medieval beauties of Cortona without sweltering or shivering, spring is the best time of year to visit. April and May are ideal, with warm, sunny afternoons for wandering the cobbled streets, and cool mornings to explore the nearby hills, carpeted in wild flowers. Summer is a beautiful time to visit Cortona, but the temperatures soar, so be sure to wear a hat and keep hydrated. Fall is great for sampling the bounty of Cortona, and winter, although chilly, is still a beautiful time to stay in Cortona and take daytrips for downhill skiing.

Hillside wonders and wildlife in Cortona

Cortona is perched on a hilltop, with stunning views of a countryside marked by rolling hills and verdant farmland. Around 2 hours east of the Adriatic Sea and 2 hours west of the Tyrrhenian Sea, Cortona is ideally situated for those who want to experience medieval architecture, rural idylls and seaside excursions. Cortona is known more for food and wine than wildlife, but those who venture out of the city and into the countryside will have the opportunity to see wild animals. Trekking over the hills affords the best chance to spot wild boar, wolves, porcupines, badgers and red foxes.

Transportation to and around Cortona

The nearest airport is in Sant Egidio Airport (PEG), located 28.9 mi (46.6 km) from the city center.

If you'd rather travel 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 vacation rental?
Fratticciola is among the most desired neighborhoods to book a vacation property in Cortona. Make yourself at home here to enjoy the relaxation and convenience that comes with having an entire place to yourself.
What is the most popular type of vacation rental accommodation in Cortona?
Villas are the most popular kind of vacation rental in Cortona, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in a variety of shapes and sizes. Filter our options to find your perfect Cortona pad.
How much does it cost to rent a vacation rental in Cortona?
The average price for a vacation rental in Cortona depends on several factors, including time of year, length of stay and property type. Whether you're searching for a sprawling house with room for friends and family or a cozy cabin perfect for just you and the kids, just add your travel dates to view stays with amazing value.
How much does it cost to rent a beach house in Cortona?
Prices for beach houses in Cortona will vary depending on the size and type of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to refine your search by amenities, nearby activities, ratings and more.
Are there pet-friendly vacation rentals in Cortona?
Happily, yes. Pick from 1,063 vacation homes that welcome pets in Cortona on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to find a property where your doggie can get in on the fun.
Can I rent a house with a pool in Cortona?
Check the "pool" box in our handy filter tool and pick from 798 houses with private pools in Cortona on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your vacation property comes with its own swimming pool.
What are popular rental amenities in Cortona?
The most popular rental amenities guests are looking for in Cortona are an electric car charging station, a beach view and a sauna. Whether you're vacationing with pals, family or even pets, Vrbo vacation rentals feature the best amenities for starting a new adventure with the people you love.
Are there large group vacation rentals in Cortona?
There are 283 properties in Cortona that can accommodate 10 or more people. Whether you're planning a vacation with extended family or an event like a party, there's plenty of space to get your group together under the same roof.
Are there vacation rentals in Cortona that welcome kids?
Gather the whole crew for the adventure of a lifetime in Cortona at one of our 1,041 family-friendly properties. A lot of these stays come with amenities that are perfect for trips with youngsters, like laundry facilities, living rooms and outdoor spaces. Just check the "Properties good for families" filter box and choose your favorite option.
What are the top attractions for families in Cortona?
Keep the kids busy at these awesome family-friendly attractions in Cortona:
  • Santa Maria Nuova
  • Santa Maria delle Grazie
  • Museum of the Etruscan Academy
Are there one-bedroom vacation rentals in Cortona?
Yes, there are 223 one-bedroom properties in Cortona to choose from. A one-bedroom vacation rental is an excellent option if it's just you and your sweetheart or if you're traveling alone. Throw in more convenience, space and privacy than a hotel, and you're sure to have a break to remember.
Can I find two-bedroom vacation rentals in Cortona?
You can select from 274 two-bedroom vacation rentals in Cortona. Put the kids in the second room or fill it with a couple of your best friends. There's enough space for whoever's lucky enough to be joining your journey.
Are there vacation rentals with WiFi in Cortona?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 491 vacation homes with WiFi in Cortona. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Cortona?
Decide on your travel dates and then make use of the filters to locate vacation rentals with air conditioning in Cortona on Vrbo. With 684 air-conditioned properties available, you can enjoy a cool and comfy stay.
How old do you have to be to rent a vacation rental in Cortona?
The minimum age permitted can differ across properties on Vrbo, so double-check the rules of the vacation home in Cortona you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Cortona for?
The length of time you can rent a vacation rental in Cortona depends on the property. Simply enter your desired dates to look at a list of options offering extended stays. With lots of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a perfect place to call your home away from home in Cortona.
Does Vrbo offer discounts for vacation homes in Cortona?
In Cortona, you'll find some fantastic bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a mini escape or a much longer stay, we've got a variety of options to match your style.

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