Cortona Vacation Rentals

Vacation Rentals in Cortona

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (55)
"Great comfortable apt. with spectacular terrace"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (56)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Casa Bacco - private house with a remarkable garden in the centre of Cortona
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Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, (40)
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Large independent villa with pool: privacy, absolute quiet and sweeping views.
Property grounds
Large independent villa with pool: privacy, absolute quiet and sweeping views.
9.2 out of 10, Wonderful, (16)
"Thanks, Etienne"
Large independent villa with pool: privacy, absolute quiet and sweeping views.
Heritage Tuscan Farmhouse with private swimming pool
Pool
Heritage Tuscan Farmhouse with private swimming pool
10.0 out of 10, Exceptional, (39)
"We had a lovely holiday at Villa Rasenna. Louise is a great host and was very helpful and replied very quickly to any queries. The kitchen is well equipped and the sitting area comfortable and homely. We made good use of the pool. We enjoyed a great meal in the villa cooked by Elena and a local wine tasting and pizza in the village. There are lovely walks from the villa in the local countryside. Would definitely recommend a holiday and we would love to return. Thanks Louise."
Heritage Tuscan Farmhouse with private swimming pool
Prestigious apartment with panoramic terrace, located in the center of Cortona.
Fridge, microwave, oven, dishwasher
Prestigious apartment with panoramic terrace, located in the center of Cortona.
9.6 out of 10, Exceptional, (4)
"This is a great home, perfect location (close to parking and walk to everything) and really nice and thoughtful manager!!!"
Prestigious apartment with panoramic terrace, located in the center of Cortona.
Cottage " I due Pini"
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Villa Primula - Holiday Rental in Cortona, Tuscany
Pool
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, (45)
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
Podere Casorbica with free parking, large garden, swimming pool.
Exterior
Podere Casorbica with free parking, large garden, swimming pool.
9.2 out of 10, Wonderful, (9)
"We are a family of five and found the property ideal for our needs, the children occupied the first floor whilst mum and dad occupied the ground floor, both have a kitchen area and lovely bathrooms with ample space to dine together on the ground floor. The property was clean and is very well maintained. The owner Giorgio met us on our arrival and managed to answer any questions we had with the help of google translate and actually came to the property every morning to clean the pool, this was...
Podere Casorbica with free parking, large garden, swimming pool.
Villa in Cortona with 6 bedrooms sleeps 12
Fridge, microwave, oven, stovetop
Villa in Cortona with 6 bedrooms sleeps 12
9.8 out of 10, Exceptional, (9)
"A terrific property in Cortona that should not be missed. A fantastic location to town requiring an uphill but not overwhelming walk or 5 minute drive to parking. The house is welcoming and stays very cool even on a warm day. Beautiful views and grounds with a comfortable pool. Wonderful place to base a trip and enjoy day trips within Tuscany. Owner and staff easy to communicate with and very available if needed. Will definitely stay there again on our next trip to Tuscany! Pictures do not do...
Villa in Cortona with 6 bedrooms sleeps 12
Villa D'Epoca Vagnucci - Cortona
Fridge, microwave, oven, stovetop
Villa D'Epoca Vagnucci - Cortona
10.0 out of 10, Exceptional, (1)
"Have stayed in area before, but not Cortona. We were taken around the property by Nonna and her grandson. A great team. They bogg live on siteNonna was attentive but not intrusive, and always left us tomatoes and basil from her garden, but spoke no english - more of a comment about us than her as it would have been great to talk to her more fully. A lovely lady. Stefano was great as translator, go to guy for info - taxi firms, air con specialists, bar to watch womens footy final! Etc A great...
Villa D'Epoca Vagnucci - Cortona
Villa Mulino - Completely renovated old mill in Tuscany
A heated pool
Villa Mulino - Completely renovated old mill in Tuscany
9.6 out of 10, Exceptional, (4)
Villa Mulino - Completely renovated old mill in Tuscany
Beautiful villa with spectacular views in a rural location
Pool | Outdoor pool
Beautiful villa with spectacular views in a rural location
9.8 out of 10, Exceptional, (36)
"Casa Sorbello was just what we were hoping for - a comfortable home in quiet, secluded surroundings with the added bonus of a generous swimming pool. The extensive views were unexpectedly glorious and we could have spent the whole time drinking in the environment if it hadn't been for all the many interesting places to visit. Our hosts were wonderfully welcoming and helpful whilst respecting our privacy. Thank you."
Beautiful villa with spectacular views in a rural location
Cosy apartment for 6 people with WIFI, pool, TV and parking
Property grounds
Cosy apartment for 6 people with WIFI, pool, TV and parking
10.0 out of 10, Exceptional, (4)
"Liebevoll restauriertes, landestypisches Haus. Sehr sauber, Vermieter immer freundlich und hilfsbereit. Landschaftlich top."
Cosy apartment for 6 people with WIFI, pool, TV and parking
Nice house in the country of Cortona.
Exterior
Nice house in the country of Cortona.
9.2 out of 10, Wonderful, (9)
"The house was neatly kept and quiet. Cortana was visible on the hill. Marzi was friendly and helpful in meeting our needs The down side was a pot holed rural road to get here and cool living room temperatures the first few days as it took the masonry walls time to warm up in the cool March temperatures."
Nice house in the country of Cortona.
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Exterior
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
9.8 out of 10, Exceptional, (52)
"The property was built in 1500 but updated recently. It definitely has its quirks related to gas and electricity. More written instructions in the home would be useful. The home is spacious with the exception of the galley style kitchen. There is a lovely courtyard that seems to be very unique to properties within the walls of Cortona. There are a couple of nice walks around Cortona. You are not too far from Sienna for a day trip."
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Belvilla by OYO Villa Letizia
3 bedrooms, WiFi
Belvilla by OYO Villa Letizia
8.8 out of 10, Excellent, (6)
"We couldn’t have been happier with our stay! Our Villa had an old world charm that was just what we wanted while staying in Tuscany! The view was AMAZING! Our host was so responsive and gave us a private tour of his Cortona. We took advantage of the hot tub and the private bath that was set up with candles and champagne! Another recommendation would be to have dinner with Luka.( our host) in his home. The food was traditionally prepared and amazing. Overall an wonderful stay!!"
Belvilla by OYO Villa Letizia
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
Fridge, microwave, oven, stovetop
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
9.8 out of 10, Exceptional, (40)
"We had a fantastic week in this lovely villa. It really does have everything you could possibly need - a real home from home. Lots of lovely spaces inside and out to enjoy. We loved sitting out in the evenings having dinner and we’re lucky to be there during the Perseus meteor shower and saw lots of shooting stars in the clear skys. We also ate out in the lovely town of Cortona - la buccia with beautifully presented food and a couple of more casual restaurants which were also excellent. The...
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
La Finestra sul Teatro
La Finestra sul Teatro
9.8 out of 10, Exceptional, (29)
"This unit met and exceeded our expectations! The host was extremely friendly and helpful, and this well-stocked home has a perfect location within the best area of Cortona. I highly recommend this unit to anyone wishing for a clean, 'light & bright' home within walking distance to everything you would ever want to do here. Thank you, Rossana, for sharing your home with us, we look forward to our next visit!"
The price is $158
$227 total
includes taxes & fees
Jun 10 - Jun 11
La Finestra sul Teatro
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See all available properties in Cortona
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cortona Vacation Rental Travel Info

Number of vacation rentals
209
Popular accommodation
Cortona villas
Known landmarks
Cathedral of Cortona, Museum of the Etruscan Academy and Casali Palace
International airports
Rome (FCO-Fiumicino - Leonardo da Vinci Intl.), Rome (CIA-Ciampino) and Perugia (PEG-Sant Egidio)

Other types of properties in Cortona you may be interested in

Monastero di Cortona Hotel & Spa
Sauna, spa tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (168)
"What a beautiful place. Staff was amazing, so helpful in every way. Lovely breakfasts in the garden. Their bartender fixes some incredible cocktails and the one night we had dinner in the hotel restaurant, everything was delicious. A word of advice: If you’re driving, insist on a SMALL rental car. Cortona is full of tiny curvy cobblestone streets some of which you must drive through to get to and from the hotel. We were offered an upgrade to a Jeep with the turning radius of a semi truck and...
The price is $314
$354 total
includes taxes & fees
Jul 2 - Jul 3
Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World
Courtyard
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, (176)
"This hotel is one of the best we have experienced. The setting is beautiful, the room was very nice, the food was the best we had in Italy (and beyond) and the service is impeccable. The entire staff is amazing, but we wanted to point out the extra efforts from Paolo, Davide and Mikelo. Now we know why we met several returning couples to this property. We will return as well!"
The price is $504
$563 total
includes taxes & fees
Jun 16 - Jun 17
Villa di Piazzano - Small Luxury Hotel of the World
Borgo Il Melone
Outdoor pool, pool umbrellas
Borgo Il Melone
4.0 star property
8.8 out of 10, Excellent, (240)
"All around excellence. Great location. Clean and spacious. "
The price is $80
$97 total
includes taxes & fees
Jun 17 - Jun 18
Borgo Il Melone
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Cortona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cortona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cortona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cortona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cortona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cortona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theater during your trip.

What are some of the best vacation home rentals that Cortona has to offer?

Podere Casorbica with free parking, large garden, swimming pool.: Visitors give good reviews to this Cortona vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a spa tub so you can immerse yourself in your vacation. Another good choice for your trip to Cortona is Nice house in the country of Cortona..

How many vacation rentals are there in Cortona?

With 275 Expedia vacation rentals, you're sure to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Enjoy the outdoors at Lake Trasimeno and Val di Chiana, or simply take in cultural attractions like Signorelli Theatre and Museum of the Etruscan Academy. While here, Piazza della Repubblica and Cathedral of Cortona are other places worth a visit.

What’s a vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.

Recent reviews of Cortona properties
Expedia verified reviews

Hotel San Michele

Hotel San Michele

5/5 Excellent
"Lovely old hotel in the centre of town. Only negative is the lack of parking nearby. "
A verified traveler from richmond stayed at Hotel San Michele
Posted 3 days ago
Hotel San Michele