Cortona Old Town vacation rentals

We found 286 vacation rentals — enter your dates for availability

Discover a selection of 26 homes, 143 apartments, and other vacation rentals in Cortona Old Town that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
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Frequently asked questions

What is the most popular type of vacation rental in Cortona Old Town?
In Cortona Old Town, apartments are the most popular type of vacation rental, with around 142 available throughout the charming streets of this historic town. These apartments typically feature fully equipped kitchens, comfortable living spaces, and some even offer stunning views of the surrounding Tuscan countryside. Many are located close to points of interest such as the Piazza della Repubblica and the Etruscan Academy Museum, making them convenient for exploring local attractions.

For travelers seeking more space, there are about 24 vacation houses available, often including multiple bedrooms, private gardens, and outdoor dining areas, ideal for families or groups. Additionally, there are around 20 villas that provide a more luxurious experience, featuring amenities like private pools and expansive terraces. There are also several cottages available, offering a rustic charm and peaceful retreats.
Are there any beach house rentals in Cortona Old Town?
In Cortona Old Town, there are about 15 beach house rentals available, primarily situated in scenic locations that offer stunning views of the surrounding Tuscan countryside. These vacation rentals typically feature charming interiors that reflect the local architecture, with amenities such as fully equipped kitchens, cozy living areas, and outdoor terraces or gardens for enjoying the beautiful landscape.
How much does it cost to rent a vacation home in Cortona Old Town?
Prices for vacation rentals in Cortona Old Town 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 Old Town 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 Old Town vacation house rentals?
You can find great discounts on house rentals in Cortona Old Town 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 are popular rental amenities in Cortona Old Town?
In Cortona Old Town, popular rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals while enjoying the local culinary ingredients. Many rentals also feature coffee and tea makers, suiting guests who appreciate a warm beverage at their convenience. Additionally, some properties are pet-friendly, permitting travelers to bring their furry companions along for the trip. For those looking for a more luxurious experience, options for private chef services are available, providing a unique opportunity to savor local Tuscan cuisine prepared right in the comfort of the rental.
Are there any family house rentals in Cortona Old Town?
In Cortona Old Town, Tuscany, there are some available family-friendly house rentals, with around 114 options spread throughout the area. This charming locale is known for its picturesque streets and breathtaking views of the Tuscan countryside, making it an ideal destination for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing meals, and outdoor terraces or gardens where children can play and families can enjoy al fresco dining.

Visitors will appreciate the proximity to local attractions such as the Etruscan Academy and the beautiful Diocesan Museum, both of which offer enriching experiences for all ages. Additionally, the area is dotted with delightful cafes and shops, great for immersing oneself in the local culture.
Can I rent a vacation home with a pool or hot tub in Cortona Old Town?
In Cortona Old Town, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 20 options for homes with pools and 17 with hot tubs. This picturesque town in Tuscany offers travelers a blend of rustic charm and modern amenities. Many of these properties come with private pools, providing a refreshing escape during the warm Italian summers, while hot tubs offer a relaxing way to unwind after a day of exploring the area's rich history and stunning landscapes.

Travelers can expect a variety of amenities, including spacious living areas, fully equipped kitchens, and outdoor dining spaces, ideal for enjoying the beautiful Tuscan weather. Some rentals may also feature scenic views of the surrounding countryside, lush gardens, and terraces, superb for soaking in the serene atmosphere.
Are there any Cortona Old Town vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cortona Old Town with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Cortona Old Town?
In Cortona Old Town, travelers will find an impressive selection of pet-friendly vacation rentals, with around 83 options available. These accommodations often feature charming rustic decor, spacious living areas, and fully equipped kitchens, allowing for a comfortable stay while enjoying the picturesque surroundings of Tuscany. Many properties also come with outdoor spaces such as balconies or gardens, superb for enjoying the beautiful Italian weather with pets.

The Old Town itself is rich in history and culture, with cobbled streets, quaint shops, and local eateries that welcome furry friends. Nearby parks and open spaces provide opportunities for leisurely walks, making it a great destination for pet owners.
Can I find long-stay vacation rentals in Cortona Old Town?
A long-stay vacation rental in Cortona Old Town is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Cortona Old Town for a vacation rental?
April is the most popular time to visit Cortona Old Town, as the charming Tuscan town comes alive with vibrant spring blooms and comfortable weather. This month marks the beginning of the tourist season, where travelers can enjoy pleasant temperatures ranging from the mid-40s to mid-70s Fahrenheit, superb for leisurely strolls through the picturesque cobblestone streets and exploring local shops and cafes.

As the peak season runs from July to September, visitors can expect a lively atmosphere filled with festivals and events. However, this bustling period can also mean larger crowds and higher prices for accommodations. Those who thrive on the energy of summer events and outdoor dining will find this time particularly enjoyable, especially with opportunities for wine tasting and enjoying local cuisine.

For travelers seeking a more budget-friendly experience, visiting in January can be a great option. While this is a quieter time in Cortona, the winter months offer a unique charm, allowing for intimate exploration of the town's rich history and stunning architecture without the bustling crowds. Plus, cozy accommodations and local trattorias create a warm and welcoming atmosphere.

Ultimately, choosing the best time to book a vacation rental in Cortona Old Town depends on your preferences.
Are there any remote work vacation rentals in Cortona Old Town?
In Cortona Old Town, Tuscany, there are numerous vacation rentals suitable for remote work, with around 171 options available. This charming medieval town, known for its stunning views and rich history, provides a superb backdrop for a productive stay. Many of the rentals come equipped with essential amenities for remote work, such as high-speed WiFi, dedicated desk spaces, and comfortable office chairs, ensuring that travelers can work efficiently while enjoying the picturesque surroundings.

In addition to work-friendly features, these properties often include cozy living areas, kitchens for preparing meals, and some even have outdoor spaces to relax after a day of work. The proximity to local cafes and shops allows for convenient breaks and a taste of the local culture. Cortona's enchanting streets, art galleries, and nearby vineyards offer plenty of opportunities to unwind and explore during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Cortona Old Town vacation rental?
Book your Cortona Old Town vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cortona Old Town?
In Cortona Old Town, visitors can experience firsthand a rich tapestry of history and culture. The Piazza della Repubblica serves as the heart of the town, where travelers can admire the impressive Palazzo Comunale and enjoy local cafes. The nearby Diocesan Museum contains remarkable works of art, including pieces by Fra Angelico.

Strolling through the charming cobblestone streets, guests can also visit the Etruscan Academy Museum, which showcases artifacts from the town's ancient past. The Basilica di Santa Margherita, perched on a hill, offers breathtaking views of the surrounding Tuscan countryside and is a must-see for those enjoying the area's scenic beauty.
Can I change or cancel my Cortona Old Town home rental booking on Vrbo?
To find Cortona Old Town vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cortona Old Town vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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