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

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710 Holiday homes

Islamorada holiday condo rental

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £326 / night

£2,403 - £2,473 / week

1 / 20

Condo rental in Islamorada

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £122 / night

£851 / week

1 / 19

Holiday home accommodation

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £265 / night

£1,855 / week

1 / 25

Islamorada holiday condo rental

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £137 / night

£928 - £1,113 / week

1 / 49

Islamorada holiday condo let

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £287 / night

£1,237 / week

1 / 23

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £353 / night

£2,467 / week

1 / 2

Home rental in Islamorada

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £315 / night

£2,201 / week

1 / 22

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £221 / night

£1,546 / week

1 / 15

Holiday condo in Islamorada

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £1,149 / night

£8,038 / week

1 / 4

Holiday condo rental

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Stay” The condo was very clean and updated! Glenn was very helpful with our stay. We even went fishing on the Reel Sharp and caught a ton of Dolphin! Us college girls will be coming again for Sailfishing season!

from £195 / night

£1,365 / week

1 / 35

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £274 / night

£1,917 / week

1 / 25

Holiday apartment in Islamorada

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £155 / night

£1,082 / week

1 / 10

Holiday condo in Islamorada

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £190 / night

£1,325 / week

1 / 26

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £243 / night

£1,701 - £1,973 / week

1 / 44

Holiday condo rental

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £202 / night

£1,412 / week

1 / 20

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £146 / night

£994 - £1,193 / week

1 / 12

Islamorada holiday townhouse accommodation

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £344 / night

£2,405 / week

1 / 34

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,641 / night

£11,483 / week

1 / 36

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £619 / night

£4,328 / week

1 / 22

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £220 / night

£1,369 / week

1 / 37

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £291 / night

£2,032 / week

1 / 13

Holiday townhouse accommodation

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £124 / night

£866 / week

1 / 33

Holiday home in Islamorada

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £884 / night

£6,183 - £10,599 / week

1 / 34

Islamorada holiday home rental

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £410 / night

£2,871 / week

1 / 43

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £161 / night

£1,126 / week

1 / 52

Holiday apartment in Islamorada

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £142 / night

£990 / week

1 / 35

Islamorada holiday home rental

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,135 / night

£7,950 / week

1 / 20

Holiday home rental

Islamorada house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £632 / night

£4,421 / week

1 / 25

Islamorada holiday home rental

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £464 / night

£1,723 / week

1 / 39

Studio rental in Islamorada with shared pool

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

from £220 / night

£1,369 / week

1 / 47

Townhouse accommodation in Islamorada with shared pool

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £508 / night

£1,899 / week

1 / 47

Townhouse rental in Islamorada with shared pool

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £508 / night

£1,899 / week

1 / 57

Holiday apartment in Islamorada

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £280 / night

£1,960 / week

1 / 35

Villa rental in Islamorada

Islamorada villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £243 / night

£1,701 / week

1 / 30

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £464 / night

£1,723 / week

1 / 31

Holiday townhouse in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £464 / night

£1,723 / week

1 / 35

Islamorada holiday home rental

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £464 / night

£1,723 / week

1 / 56

Holiday apartment in Islamorada

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £148 / night

£1,033 / week

1 / 42

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £464 / night

£1,723 / week

1 / 51

Holiday townhouse with shared pool in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £464 / night

£1,723 / week

1 / 46

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Islamorada holidays

Islamadora, or "Village of Islands", refers to the collection of islands in the Florida Keys including the Keys of Tea Table, Upper and Lower Matecumbe, Plantation, and Windley. Every destination in Islamadora offers access to the very best of this island paradise. The beautiful beaches, emerald golf courses, luxurious spas, and charming local museums in Islamadora make this the perfect place for a family holiday. Islamadora also offers easy access to Everglades National Park, an ecological destination that draws visitors from all over the world to see its dazzling biodiversity and elusive marine life. Come to Islamadora to play, explore, learn about the culture and history of the Florida Keys or simply relax. After the sun goes down, experience the world-class seafood restaurants and laid back vibe of Islamadora's night life.

Here are a few additional suggestions as you plan your trip:

  • Visit the Theatre of the Sea: This place is a Nature Center, aquarium, and theatre all rolled into one. Come here to learn about the marine ecosystems of the Florida Keys and interact with dolphins and sea lions.
  • Explore the wharf: Go fishing, rent a boat, or feed the gigantic tarpon at Robbie's marina. There are also sport fishing marinas in Islamadora where you can schedule charter trips and pursue large game like swordfish.
  • Visit the History of Diving Museum: The interactive displays and extraordinary collection of artefacts at the diving museum provide a great way to learn about maritime history and culture.
  • Take an eco-tour: Explore the Everglades National Park by boat, one of the best ways to see marine plants and animals in their natural habitats.
  • Play on the beach: Annie's Beach offers a clean stretch of beautiful white sand and blue ocean waves, perfect for a relaxing day with children. Go swimming, surfing, parasailing, rent a boat, or just sunbathe with a good book.
  • Visit the Windley Key Fossil Reef Geological State Park: This park is known for its hiking trails but more so for its incredible fossilised coral reefs.

Finding a place to stay will be easy in Islamadora, even if you arrive during the height of the summer. Find a quaint cottage for a romantic getaway, a summer home big enough for your whole family, or a luxury beach villa for you and some friends. No matter what you plan to do while you're here, you'll be able to find the perfect holiday rental to meet your needs.

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