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Vacation Rentals & Apartments in Cortona

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Vacation Rentals & Apartments in Cortona

About Cortona

3,991 apartments

VillaStefania Old Farmhouse Great View on Cortona

Cortona villa

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$325

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Cortona - 78001

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$136

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Villa Borgo delle Spighe- A nice country estate sets a wonderful scenery

Cignano villa

7 bedrooms / 7 bathrooms / sleeps 14

“Amazing all around!!!” Villa Luna (Casa Nebbie) is amazing. The house was well appointed, the kitchen huge and well stocked, and the view simply amazing. Madeline (the property manager) was very helpful as well. The bedrooms, linens, etc. were also

Price per night from

$325

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Barbagianni 2+2

Cortona villa

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$149

1 / 32

Of Friends House

Montecchio house

3 bedrooms / 2 bathrooms / sleeps 6

“absolutely marvellous” un paradiso nel paradiso, tutto veramente eccellente, la villa, la piscina, il panorama, il servizio e l'accoglienza.

Price per night from

$130

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Bucchero 9

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$98

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Villa delle Sophore 16 + 4

Cortona villa

8 bedrooms / 7 bathrooms / sleeps 20

Price per night from

$532

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Maccari Apartment

Cortona apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$114

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Princess 5 + 2

Montalla villa

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$276

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Apartment Cara Mia

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$68

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Il Nido a contemporary countrychic Villa with pool

Montecchio villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$138

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3 bedroom villa in Cortona. Private pool and garden. (BFY13455)

Montalla house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$255

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Villa Il Casone

Montecchio villa

7 bedrooms / 5 bathrooms / sleeps 22

Price per night from

$325

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Price per night from

$405

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Villa Luisella - Bellavista, unique panoramic apartment with garden

Cortona house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

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Villa Luisella a jewel in the heart of Cortona

Cortona villa

7 bedrooms / 7 bathrooms / sleeps 16

Price per night from

$512

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Bucchero 4

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$98

1 / 20

Casa Bellavista

Cortona house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$244

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Villa La Pergola

Cortona villa

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$243

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Casale Fontocchio with nice swimming pool

Cortona villa

5 bedrooms / 5 bathrooms / sleeps 4

Price per night from

$292

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Perfect Stay at Incredible Prices

Cortona apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$89

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Villa Arianna corner between Tuscany and Umbria

Cortona villa

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$354

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Villa Conca D'oro

Cortona apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$203

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Apartment Luna

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$122

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Casale Cinque Valli 8

Cortona villa

4 bedrooms / 4 bathrooms / sleeps 8

“Fantastic Week!” The home was great, very roomy, very isolated so no neighbors to annoy, and the surrounding area was as picturesque as a painting. We enjoyed the pool and the outdoor dining area every day. We had the chef service come in two days,

Price per night from

$272

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Villa il Giuggiolo - Azienda Fontelunga

Cortona house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 56 minutes

Price per night from

$354

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Casa del Sole 4

Cortona villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$201

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Home Saint Lucia

Montalla house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$113

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Tuscany Large villa with Private Pool, Villa Grazia Tuscany , - Tuscany, Family

Montecchio house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 34 minutes

Price per night from

$312

1 / 45

Villa Oleandro

Montalla house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$210

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The Hamlet of Greta 10 + 2

Cortona villa

5 bedrooms / 7 bathrooms / sleeps 12

Price per night from

$308

1 / 52

La Graziosa, graceful cottage with lovely pool.

Cortona villa

2 bedrooms / 1 bathroom / sleeps 4

“Quiet beautiful place” We had an excellent holiday in this place. We will surely come back !

Price per night from

$114

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Tuscan Dream Home in Cortona: Pool, WIFI, Magical

Cortona house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$331

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Casa La Dolce Vita beautiful panoramic windows.

Cortona house

2 bedrooms / 2 bathrooms / sleeps 6

“A fabulous exprience staying on the main street of Cortona” We stayed a total of 4 months in Casa Giulia and found it to be the perfect location.The large(about40 sq metres) was perfect. The view of the Val De Chiana are spectacular. Sun rise,sun set

Price per night from

$137

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Villa Alma: the pool is a dream

Cortona villa

4 bedrooms / 4 bathrooms / sleeps 8

“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 vill

Price per night from

$340

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Private villa with pool near Cortona, Villa I Girasoli

Cignano villa

7 bedrooms / 6 bathrooms / sleeps 17

Price per night from

$312

1 / 32

Villa Melody: charming villa very near to Cortona

Cortona villa

3 bedrooms / 2 bathrooms / sleeps 6

“Unforgetable!!!” Melody House and Cortona will be in remembrance of the best family vacations. The reception team Terretrusche is perfect.

Price per night from

$163

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2 Bedroom Vacation Rental at Appartamento del Borgo

Cortona apartment

2 bedrooms / 2 bathrooms / sleeps 4

“The most authentic Tuscan experience we've ever had.” This is a beautiful, comfortable apartment with an inspiring view of the Val di Chiana from the kitchen window. It is the perfect base from which to explore the town of Cortona - a site teeming wit

Responds fast! avg. 1 hour 44 minutes

Price per night from

$125

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Viewing 38 of 3,991

About Cortona

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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.

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