Cortona Old Town vacation rentals
We found 288 vacation rentals — enter your dates for availability
Discover a selection of 25 homes, 182 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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Find the best place to stay - Cortona Old Town

La Terrazza sulla Valle, with private terrace overlooking the valley!
Sleeps 6 · 2 bedrooms · 2 bathrooms

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace
Sleeps 7 · 3 bedrooms · 2 bathrooms

Casa Vinalia inside the Etruscan walls of Cortona
Sleeps 5 · 2 bedrooms · 2 bathrooms

Romantic Lux Country House
Sleeps 8 · 3 bedrooms · 3 bathrooms

Casa Bacco - private house with a remarkable garden in the centre of Cortona
Sleeps 6 · 3 bedrooms · 2 bathrooms

Apartment in the heart of Cortona
Sleeps 3 · 1 bedroom · 1 bathroom
Top rated rentals - Cortona Old Town

Review for stay from 14 June 2025 to 21 June 2025
Mega schönes kleines Ferienhaus, welches alles bietet, was man für einen entspannten Urlaub braucht. Wir waren mit 4 Erwachsenen und 2 großen Hunden und alle waren rundum begeistert. Michele ist ein wirklich toller Vermieter, der jederzeit über WhatsApp mir Rat und Tat zur Seite steht. Beigeistert hat mich auch, dass es endlich mal ein italienischer Vermieter war, mit dem man sich problemlos auf Englisch unterhalten konnte.
Wir nannten die Unterkunft scherzhaft: Villa "Sorglos", da wirklich alles da ist was man für einen entspannten Urlaub braucht. Vom Spülmittel, über Spülmaschinentabs, verschiedenes Waschpulver, Espressokapseln, Grillkohle, Badehandtücher für die Liegen am Pool, Bademantel, Hotelschlappen, etc.
Wir fahren seit 2008 jedes Jahr nach Italien in die verschiedensten Ferienhäuser, aber so eine Rundumversorgung haben wir noch nie erlebt.
Kerstin K.
Stayed Jun 2025

My house in Cortona
We thoroughly enjoyed our 1 month stay at this apartmentThe location was superb, and Pier Luigi, our host, could not have been nicer. And we loved Cortona.
Fred C.
Stayed Apr 2025

9 days in Cortona
Very convenient location. Great views. But the stairs are bit of a challenge for fat people like myself. But we made it work.
toby s.
Stayed Oct 2024

Great apartment!
Very roomy, well equipped, and a really good location. Would stay again!
Mark E.
Stayed Jul 2024

The views were just the beginning!
Cortona is a magical place and the Rooftop Nest was perfect! Margherita was a fabulous host that communicated well and even arranged a dinner reservation for us. This was the best meal of our vacation. The Rooftop nest is roomy and comfortable, with two balconies and endless views. The town has lovely shops and an active nightlife. There was a market being set up on Sunday but we were off to our next destination.
Shawn H.
Stayed Jun 2024

Wonderful week in Cortona.
The house and garden are beautiful and cozy. The view from the den and upstairs bedrooms is absolutely breathtaking. It is very centrally located with quick access to the piazzas with shopping and dining, and it is just far enough up the hill to help you burn off all the wine and pasta calories, but not far enough up the hill to be difficult. The together in Tuscany team managing the place are very friendly and professional and made everything smooth-including getting a driver to and from the train. There is so much to see and do in this charming town that we should have stayed another week or two. I Will cheerfully return here in the future.
James H.
Stayed Jun 2024

Lovely place in a great location.
This place was perfect, and the hosts were delightful. Highly recommend.
Stacey L.
Stayed Jun 2023

Perfect in Every Way
We rented this house for a month. We loved it here and felt very comfortable calling it home for so long. Fully renovated with modern appliances just as pictured. Kitchen is equipped with everything you need to cook a meal, which we did 1/2 the time. Beds are comfortable and bathrooms big. Washer / dryer was a plus. Walking up and down the hills kept us in great shape to eat all the pasta we wanted! From here, we traveled by train to Florence, Lake Trasimeno, Arezzo. Owner was quick to respond if we have a question and local contact was very helpful. Highly recommend for anyone looking for a home away from home.
Jane P.
Stayed Apr 2023
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
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 about 144 available throughout the picturesque streets. These apartments often feature charming decor, fully equipped kitchens, and cozy living areas, making them great for travelers wanting a local experience close to attractions like the Piazza della Repubblica and the Etruscan Academy. For those seeking more space, around 24 vacation houses are available, typically offering multiple bedrooms, private gardens, and outdoor seating areas, ideal for families or groups. Additionally, there are several villas and cottages that provide a more luxurious stay, often set in serene surroundings with beautiful views of the Tuscan 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, travelers can expect a variety of vacation rental amenities that enhance their stay in this charming Tuscan setting. Most rentals come equipped with kitchens, allowing guests to prepare their own meals and enjoy the local produce. Many properties also feature coffee and tea makers, superb for starting the day with a warm beverage. For those traveling with pets, numerous rentals permit animals, ensuring that guests can bring their furry companions along. Service animals are also accommodated, suiting the needs of all visitors. Additionally, families will like the availability of travel cribs, making it easier for those with young children to enjoy a comfortable stay.
Can I find family house rentals in Cortona Old Town?
In Cortona Old Town, Tuscany, there is a substantial selection of family-friendly house rentals—approximately 111 options are available. This charming historic area offers a variety of accommodations that cater to families looking for a memorable stay. Many of these homes feature spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play or families can enjoy al fresco dining while soaking in the stunning views of the Tuscan hills.Visitors will appreciate the proximity to local attractions, such as the picturesque Piazza della Repubblica and the Etruscan Academy Museum, which provide cultural insights and family-friendly activities. Additionally, the local markets and shops offer a delightful experience, superb for immersing oneself in the vibrant Italian lifestyle.
Can I rent a vacation home with a pool or hot tub in Cortona Old Town?
In Cortona Old Town, there are several vacation homes available for rent that feature both pools and hot tubs, with around 12 options for homes with pools and 14 options with hot tubs. This picturesque town in Tuscany offers a unique blend of history and stunning landscapes, making it a great getaway. Many of these rentals boast amenities such as private pools where guests can relax and enjoy the sun, as well as hot tubs for a soothing soak after a day of exploring the charming streets and local attractions.Travelers can also expect fully equipped kitchens, spacious living areas, and outdoor terraces that provide beautiful views of the surrounding Tuscan countryside.
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.
Can I book pet-friendly vacation rentals in Cortona Old Town?
Yes, there are numerous pet-friendly vacation rentals available in Cortona Old Town, with around 67 options to choose from. Travelers can expect a variety of accommodations that typically feature amenities such as fully equipped kitchens, comfortable living spaces, and charming decor that reflects the local Tuscan style. Many properties also offer outdoor spaces, which can be ideal for enjoying the beautiful surroundings with pets.Cortona's historic character provides a picturesque backdrop for your stay, with its narrow streets, ancient buildings, and scenic viewpoints. The area is also home to pet-friendly parks and open spaces where you can stroll with your furry companion, making it a delightful 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 one of the best months to visit Cortona Old Town, as the spring weather brings mild temperatures and blooming landscapes that enhance the charm of this historic Tuscan town. During this time, visitors can enjoy comfortable daytime temperatures ranging from the mid-50s to low 70s Fahrenheit, making it ideal for leisurely strolls through cobblestone streets and exploring local markets.The peak tourist season in Cortona runs from July to September, when the town becomes a bustling hub for travelers seeking to immerse themselves in the vibrant local culture and stunning scenery. This summer period is marked by lively festivals, outdoor dining, and ample opportunities for sightseeing. However, if you prefer a more tranquil experience with fewer crowds, visiting in April or even May can provide you with a delightful blend of pleasant weather and a more relaxed atmosphere.For those looking to save while still enjoying everything Cortona has to offer, consider planning your visit in January. While this month is less popular, it presents a unique opportunity to experience the town in a quieter setting, allowing for intimate exploration of its rich history and artistic heritage without the hustle and bustle of peak tourism.
Are there any remote work vacation rentals in Cortona Old Town?
In Cortona Old Town, Tuscany, there are numerous remote work-friendly vacation rentals available, with around 166 options to choose from. This charming medieval town offers a blend of history and stunning landscapes, making it an appealing destination for remote workers. Many rentals come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desk chairs, ensuring that travelers can maintain productivity during their stay.The picturesque streets of Cortona are lined with historic buildings, and you'll find local cafes and restaurants nearby, providing a lovely atmosphere for breaks or casual meetings. Additionally, the scenic views of the Tuscan countryside serve as a beautiful backdrop to inspire creativity. 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, Tuscany, Italy?
In Cortona Old Town, visitors can immerse themselves in the rich history and stunning architecture that defines this charming Tuscan town. The Piazza della Repubblica serves as the heart of the town, where travelers can admire the beautiful Palazzo Comunale and enjoy a coffee at one of the local cafes. Just a short walk away, the Diocesan Museum houses an impressive collection of Renaissance art, including works by Fra Angelico.For those interested in breathtaking views, the Basilica di Santa Margherita offers panoramic vistas of the surrounding countryside and is well worth the climb up to its hilltop location. Nearby, the Etruscan Academy Museum showcases artifacts from the ancient civilization that once inhabited the area, providing insight into Cortona's historical significance.Exploring the cobblestone streets, visitors will encounter quaint shops, art galleries, and traditional trattorias serving authentic Tuscan cuisine. The town is also known for its festivals, such as the Cortona Antiquaria, where antique lovers can browse for unique finds.
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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