Vacation Rentals & Apartments in Cortona

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1,925 apartments

Apartment Luna

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$196

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

$327

Villa Eleonora

Montalla house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$294

Typical apartment in the Tuscan town of Cortona

Cortona apartment

  • 1 bathroom
  • sleeps 3

Price per night from

$92

Villa Del Sole

Cortona villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 13

Price per night from

$442

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

$366

Villa Fastia A

Montalla house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 53 minutes

Price per night from

$81

Il Cipresso apt in farmhouse Casa Contea with pool

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$220

Maccari Apartment

Cortona apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$161

Casa Mia a CORTONA: Overlook Valdichiana & Tuscany

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$110

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

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$220

Casale Girifalco

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$710

Villa Fastia B

Montalla house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 53 minutes

Price per night from

$75

Casa Liliana

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$446

Price per night from

$216

Villa Magnolia

Teverina villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$469

Villa Ginestra

Teverina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$356

Villa Oleandro

Montalla house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$254

La Contea with swimming pool and panoramic view near Cortona

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$670

Villa Vittoria

Montalla villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$669

Price per night from

$185

Tuscan Dream Il Gonfianuvole Antica Quercia Verde

Cortona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$216

Villa Fastia Grande

Montalla house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 53 minutes

Price per night from

$338

Price per night from

$495

Villa Lamina Grande

Cortona house

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 1 hour 53 minutes

Price per night from

$1,348

Cortona Suite B&b - Wellness Suite Hammam

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$200

DELUXE ROMANTIC ROOM - LA CORTE DI AMBRA

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$195

Zefferini apartment

Cortona apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$241

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

Montecchio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$160

Tullia

Cortona villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$799

Albachiara 8, Emma Villas

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$610

Cortona Suite B&b - Passion Suite Baldacchino

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$133

Casa Caterina

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$174

Price per night from

$287

Villa Evarne

Cortona house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 53 minutes

Price per night from

$616

La Piazzetta apartment

Cortona apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$126

Cortona - 75001

Cortona house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$161

Viewing 38 of 1,925
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
Villa Eugenio, authentic villa walk to village
Charming, authentic tusan villa in a very quiet environment, goo

Very comfortable villa. Large pool cleaned every morning. Great view on Montepulciano valley. Hudge bedrooms with separate bathrooms. Good located for trips to Cortona, San Giminiano, Montepulciano, Perugia, Siena. Train station and supermarket at 5 minutes. … 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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