Vacation Rentals & Apartments in Cortona

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1,933 apartments

Apartment Luna

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$201

Elegant Vacation Rental in Cortona Tuscany, Moses

Cortona house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“A beautiful palace in a heavenly location.” We loved our stay in the Moses Palace. It is centrally located in the gorgeous city of Cortona, and Roberto could not have been more helpful and accommodating for us.

Price per night from

$344

Cells Farinaio

Cortona house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$335

Apartment "Leonardo"in cortona's country (2bd)

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

“A place full of charm” We were three friends Spanish for a week and the room was unforgettable. The functional and bright apartment, located in a beautiful place, we loved it. Lorenzo, the owner is a lovely person and always willing to help beyond what we expected. Car is necessary to explore the region, which is wonderful. We are delighted and indeed the place again. Lorenzo and Silvia Thanks for your hospitality and for all you know, even by my ineptitude, which I appreciate from heart. You are wonderful and just hope to return.

Price per night from

$63

Villa Eleonora

Montalla house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$301

Typical apartment in the Tuscan town of Cortona

Cortona apartment

  • 1 bathroom
  • sleeps 3

Price per night from

$94

Villa Del Sole

Cortona villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 13

Price per night from

$453

Vacatoin Rentals at Le Celle Del Farinaio in Short

Cortona villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Charming house with a beautiful garden” Le Celle lies on the hillside, secluded and peaceful. The house is of high standard and keeps cool during the hot season. The garden is amazing, full of so many different flowers, plants and trees. The Tarquini family are friendly and helpful, and we did not miss anything during our stay!

Price per night from

$374

Villa Fastia A

Montalla house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 45 minutes

Price per night from

$83

Il Cipresso apt in farmhouse Casa Contea with pool

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$225

Maccari Apartment

Cortona apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$165

Casa Mia a CORTONA: Overlook Valdichiana & Tuscany

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$113

La Quercia in Casa Contea Cortona w sw-pool & view

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$225

Casale Girifalco

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$727

Villa Fastia B

Montalla house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 45 minutes

Price per night from

$76

Casa Liliana

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$457

Price per night from

$221

Villa Magnolia

Teverina villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$383

Villa Ginestra

Teverina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$364

Villa Oleandro

Montalla house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$260

La Contea with swimming pool and panoramic view near Cortona

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$686

Villa Vittoria

Montalla villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$685

Price per night from

$190

Tuscan Dream Il Gonfianuvole Antica Quercia Verde

Cortona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$221

Villa Fastia Grande

Montalla house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 45 minutes

Price per night from

$346

Price per night from

$507

Villa Lamina Grande

Cortona house

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 45 minutes

Price per night from

$1,380

Cortona Suite B&b - Wellness Suite Hammam

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$205

DELUXE ROMANTIC ROOM - LA CORTE DI AMBRA

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$200

Zefferini apartment

Cortona apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$247

Villino Cortona - Casa vacanze con piscina privata, wifi, Ac - Toscana

Montecchio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$154

Tullia

Cortona villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$798

Albachiara 8, Emma Villas

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$625

Cortona Suite B&b - Passion Suite Baldacchino

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$136

Casa Caterina

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$179

Price per night from

$294

Villa Evarne

Cortona house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 45 minutes

Price per night from

$631

La Piazzetta apartment

Cortona apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$129

Viewing 38 of 1,933
rentals in Cortona

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About Cortona

With magnificent panoramas, great old Italian architecture and some of the best food in the area, Cortona is the ideal destination for a romantic getaway or family vacation. The cobblestone streets, quaint buildings, and winding roads of Cortona make it one of the best walking towns in the area. If you are looking for great restaurants and shopping, be sure to check out Piazza Signorelli.

Here are a few additional suggestions of things to do in Cortona:

  • Cooking Classes: Several hotels in the area offer half-day and full-day courses in the art of making traditional Italian dishes.
  • The Archaeological Park: This route takes you along several Roman roads and past some beautiful architecture.
  • Visit the Churches: Cortona is home to beautiful churches including the Duomo and Eremo Le Celle.
  • Visit the Tombs: The Etruscan tombs are arguably the biggest attraction in the area.
  • Palazzo Comunale: The town hall that was built in the early 13th century remains largely intact and offers guided tours.

Not surprisingly, many of the festivals in Cortona revolve around the amazing culinary attractions in the area. The biggest festival is the Sagra della Bisteca in August, which celebrates the steak from the local Chianina cows. The other main festival in the area is the Giostra dell'Archidado in May, an archery competition where representatives of the city's quarters compete while wearing historical costumes. The annual grape harvest, typically held in late September or early October, is another big event for Cortona.

Whether you want a condo with panoramic views of the vineyards out your front door, an apartment that's steps from all the major attractions and fine dining options, or a more secluded luxury villa in the outer parts of town, there's a vacation rental available to help you get the most out of your European getaway.

Top Destination reviews

Vacatoin Rentals at Le Celle Del Farinaio in Short
Charming place in Toscana. You will never forget your stay

Charming villas on the hills of the Trasimeno lake with beautiful scenery and relaxing. Time stops during the stay. Each has its place and benefits as it means facilities available: swimming, Mountain biking. Difficult to leave the house yet conveniently placed for exploring the treasures of Tuscany and Umbria. Mauro, the owner upon arrival, established a welcoming atmosphere and is at your disposal during your stay. Everything is perfect even last evening organized by our host. An unforgettable stay. Bravo Mauro (e toute la famaglia Tarquini). Grazie.see more
Villa Alma: the pool is a dream
Great for a group

We were a party of 8 and we really enjoyed the space this place had for us all and the pool was very welcome in the heat. Great restaurant at the very top of the hill...we went twice. The cooking class was such fun too at the villa. Only downside was the electrical system cutting out and leaving us with no power on a few occasions. The electrician came quickly to get it back on though. We definitely stay again. Very pretty place.see more
Apartment "Leonardo"in cortona's country (2bd)
Great location to visit many tourist cities close by

Very clean and confortable apartment, with good central heating and fast internet. Very quiet neighbourhood. Easy and really fast access from the motorway. The meeting point for check-in was in Camucia Central Station, from where the owner guided us to the apartment. In Camucia there is a Coop supermarket (medium sized - very good), wich is about 7km (5 minutes by car) from the apartment. The owners are great people. Always helpful. During our stay we visited Cortona, Arezzo, Montepulciano, Pienza, Assisi, Siena and Perugia. We did not went to Gubbio, wich is also near, because it was raining. You can get to those cities very fast by car, most of then not using toll motorways. The only thing we did not like in the apartment is that in the living room there is a lot of decorative itens in shelves. They are beautiful but takes free space that could be used by the guests. We had to move things to clear space for the laptop and smaller things. Note for future guests: Only rent if you have a car. There may be a lot of mosquitoes in the summer, as it is a rural area. We went in the end of the winter and had no issues. The stairs to the bedroom are narrow and not suitable for the elderly.see more
Diana Garden: pool in a unique flower garden.
La dolce vita!!!

We have stayed at Villa Maria Della Rose three times and each time it's been a joy, the spring visit was beautiful, the weather was superb and the evenings cool. The villa is so comfortable and beautifully appointed a true home from home. We also visited in July/August the sun was hot and the evenings were filled with barbecues and Prosecco and Vittorio sent us a wonderful chef who cooked fabulous food for us, what a luxury. The villa has 1metre thick walls so it stays cool inside, and when it was very warm in the evening there is air conditioning in the bedrooms, oh and the beds, wow, King size super comfortable beds. Before discovering this villa we had stayed in the surrounding hills, but we found being inside the walls to be truly magical. In fact leaving this amazing garden was the hardest part of all. We are hoping to go back for Xmas this year ... If it's not already booked. H&E; Notting Hill Londonsee more
Casa La Dolce Vita beautiful panoramic windows.
Old World Charm

My mother and I spent 2 weeks at Casa Giiulia in September 2012. This old city centre apartment was all we could hope for and more. A very large rental with fabulous views of the rooftops of Cortona as well as the Valley below. If stairs are an issue, be aware there are several stairs to climb to reach this apartment. A Great kitchen to stay in and cook, but the unit is also only steps away from grocers, bakers, pasta makers not to mention all the local restaurants. Couldn't have asked for a better rental. The Terre Trusche rental office is also on the ground floor of this building and all the staff are always available to assist you with any queries.see more
Villa Borgonuovo, marvelous example of the traditional tuscan farmhouse.
Lovely Family house near Cortona

We had a lovely time there. Everything was more than oké! The swimming pool excellent. The garden beautiful. The house beautiful and had comfort. Minus were the beds. Too hard. … see more

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