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Holiday Lettings
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> Florida Keys
> Holiday rentals and villas in Islamorada

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

Price per night

£1 £750 -

Bedrooms

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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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662 Holiday homes

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Holiday home in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £181 / night

£1,262 / week

1 / 22

Lower Matecumbe Key holiday home rental

Lower Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £295 / night

£2,060 / week

1 / 30

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 18

from £1,460 / night

£10,216 / week

1 / 30

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £338 / night

£2,362 / week

1 / 20

Holiday villa in Upper Matecumbe Key

Upper Matecumbe Key villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Pricing unknown

1 / 11

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from £1,129 / night

£7,898 / week

1 / 23

Upper Matecumbe Key holiday home rental

Upper Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £643 / night

£4,501 / week

1 / 30

Holiday home in Lower Matecumbe Key

Lower Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £179 / night

£1,251 / week

1 / 17

Holiday home in Lower Matecumbe Key

Lower Matecumbe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £387 / night

£2,707 / week

1 / 30

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £551 / night

£3,855 / week

1 / 30

Upper Matecumbe Key ski home to rent.

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £335 / night

£2,346 / week

1 / 21

Lower Matecumbe Key ski home to rent.

Lower Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £261 / night

£1,828 / week

1 / 30

Ski home to rent in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £427 / night

£2,987 / week

1 / 21

Ski home to rent in Lower Matecumbe Key

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £201 / night

£1,407 / week

1 / 24

Upper Matecumbe Key ski home to rent.

Upper Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £312 / night

£2,178 / week

1 / 24

Ski home to rent in Lower Matecumbe Key

Lower Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £432 / night

£3,019 / week

1 / 30

Ski home to rent in Lower Matecumbe Key

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £436 / night

£3,052 / week

1 / 30

Upper Matecumbe Key ski condo to rent.

Upper Matecumbe Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £423 / night

£2,960 / week

1 / 21

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £532 / night

£3,720 / week

1 / 25

Lower Matecumbe Key holiday condo rental

Lower Matecumbe Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £222 / night

£1,553 / week

1 / 16

Holiday home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £481 / night

£3,364 / week

1 / 30

Upper Matecumbe Key holiday home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £403 / night

£2,820 / week

1 / 9

Upper Matecumbe Key holiday home rental

Upper Matecumbe Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £851 / night

£5,958 / week

1 / 28

Holiday home in Lower Matecumbe Key

Lower Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £349 / night

£2,443 / week

1 / 19

Upper Matecumbe Key holiday home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £1,022 / night

£7,149 / week

1 / 27

Holiday home accommodation

Lower Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £882 / night

£6,173 / week

1 / 0

Lower Matecumbe Key holiday home rental

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £176 / night

£1,230 / week

1 / 29

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £214 / night

£1,497 / week

1 / 21

Home rental in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £345 / night

£2,410 / week

1 / 30

Upper Matecumbe Key ski home to rent.

Upper Matecumbe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £599 / night

£4,189 / week

1 / 30

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £607 / night

£4,243 / week

1 / 30

Home rental in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £421 / night

£2,944 / week

1 / 30

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £498 / night

£3,483 / week

1 / 20

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £299 / night

£2,092 / week

1 / 30

Lower Matecumbe Key holiday home rental

Lower Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £905 / night

£6,335 / week

1 / 0

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £265 / night

£1,854 / week

1 / 5

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £165 / night

£1,154 / week

1 / 30

Holiday home accommodation

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £265 / night

£1,855 / week

1 / 30

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £337 / night

£2,356 / week

1 / 24

Holiday home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £1,368 / night

£9,575 / week

1 / 30

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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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