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Holiday Lettings
> Europe
> Italy
> Tuscany
> Province of Arezzo
> Villas and holiday rentals in Cortona

Villas in Cortona and Holiday rentals - Holiday Lettings - Holiday Rentals Cortona

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£1 £750 -

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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839 Holiday homes

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Holiday villa in Cortona

Cortona villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

from £267 / night

£1,863 / week

1 / 30

Holiday apartment in Cortona

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £79 / night

£554 / week

1 / 23

Cortona ski home to rent.

Cortona house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £159 / night

£1,113 / week

1 / 24

Col di Morro holiday villa rental

Col di Morro villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £334 / night

£2,338 / week

1 / 30

Holiday villa in Cortona

Cortona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £210 / night

£1,468 / week

1 / 30

Holiday home in La Dogana

La Dogana house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £169 / night

£1,180 / week

1 / 30

Holiday villa in Mercatale

Mercatale villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £268 / night

£1,875 / week

1 / 19

Holiday villa in Cortona

Cortona villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £83 / night

£582 / week

1 / 12

Holiday home in Col di Morro

Col di Morro house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £128 / night

£892 / week

1 / 30

Ski villa to rent in La Dogana

La Dogana villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £290 / night

£2,027 / week

1 / 28

Holiday apartment in Cignano

Cignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £94 / night

£655 / week

1 / 27

Barullo-Centoia holiday apartment rental

Barullo-Centoia apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £163 / night

£1,141 / week

1 / 30

Holiday villa in Cortoreggio

Cortoreggio villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £234 / night

£1,638 / week

1 / 30

Holiday villa in Cortoreggio

Cortoreggio villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £329 / night

£2,298 / week

1 / 30

Holiday cottage in Cortoreggio

Cortoreggio cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £53 / night

£367 / week

1 / 30

Holiday home in Cortona

Cortona house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £204 / night

£1,423 / week

1 / 30

Barullo-Centoia holiday apartment rental

Barullo-Centoia apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £140 / night

£977 / week

1 / 28

Creti holiday apartment rental

Creti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £103 / night

£717 / week

1 / 30

Holiday apartment in Cortona

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £113 / night

£791 / week

1 / 30

Col di Morro holiday home rental

Col di Morro house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £209 / night

£1,463 / week

1 / 30

Appalto holiday villa rental

Appalto villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £125 / night

£870 / week

1 / 20

Holiday home in Torreone

Torreone house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £71 / night

£492 / week

1 / 19

Holiday villa in Cortona

Cortona villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £107 / night

£746 / week

1 / 19

Holiday apartment rental

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £87 / night

£604 / week

1 / 27

Holiday villa in Teverina

Teverina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £129 / night

£904 / week

1 / 28

Teverina holiday villa rental

Teverina villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £126 / night

£881 / week

1 / 19

Holiday apartment in Cortona

Cortona apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

from £75 / night

£525 / week

1 / 26

Holiday condo in Cortona

Cortona condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £202 / night

£1,412 / week

1 / 30

Holiday apartment in Cortona

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £55 / night

£384 / week

1 / 22

Cortona holiday villa rental

Cortona villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £247 / night

£1,728 / week

1 / 30

Villa rental in Schiavazzolo

Schiavazzolo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £128 / night

£892 / week

1 / 30

Barullo-Centoia holiday apartment let

Barullo-Centoia apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £150 / night

£1,050 / week

1 / 28

Montalla ski villa to rent.

Montalla villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 12

from £490 / night

£3,427 / week

1 / 30

Holiday villa in Cortona

Cortona villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

from £412 / night

£2,880 / week

1 / 18

Holiday villa rental

Monsigliolo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £235 / night

£1,643 / week

1 / 30

Holiday apartment in Cortona

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £128 / night

£892 / week

1 / 21

Holiday villa in Cortona

Cortona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £174 / night

£1,214 / week

1 / 26

Teverina holiday villa rental

Teverina villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £151 / night

£1,056 / week

1 / 27

Villa rental in Pietraia

Pietraia villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £204 / night

£1,429 / week

1 / 30

Holiday villa accommodation

Teverina villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £136 / night

£949 / week

1 / 27

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Cortona holidays

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 holiday. 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 holiday rental available to help you get the most out of your European getaway.

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