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> Villas and holiday rentals in Florida Keys

Villas in Florida Keys and Holiday rentals - Holiday Lettings - Holiday Rentals Florida Keys

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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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7,358 Holiday homes

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Ski cottage to rent in Little Torch Key

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £227 / night

£1,583 / week

1 / 17

Holiday condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £292 / night

£2,040 / week

1 / 30

Holiday home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £431 / night

£3,016 / week

1 / 26

Holiday cottage rental

Cudjoe Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £273 / night

£1,906 / week

1 / 28

Holiday condo in Tavernier

Tavernier condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £434 / night

£3,039 / week

1 / 30

Tavernier holiday home rental

Tavernier house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £395 / night

£2,762 / week

1 / 30

Holiday condo in Tavernier

Tavernier condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £271 / night

£1,891 / week

1 / 30

Holiday home in Tavernier

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £382 / night

£2,668 / week

1 / 30

Holiday condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £299 / night

£2,089 / week

1 / 30

Ski cottage to rent in Summerland Key

Summerland Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £183 / night

£1,276 / week

1 / 17

Tavernier ski condo to rent.

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £319 / night

£2,232 / week

1 / 30

Tavernier holiday home rental

Tavernier house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £393 / night

£2,749 / week

1 / 30

Holiday condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £373 / night

£2,606 / week

1 / 30

Tavernier holiday home let

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £267 / night

£1,867 / week

1 / 30

Holiday home in Tavernier

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £327 / night

£2,287 / week

1 / 30

Marathon ski condo to rent.

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £431 / night

£3,018 / week

1 / 30

Holiday cottage in Cudjoe Key

Cudjoe Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £256 / night

£1,787 / week

1 / 17

Cottage letting in Cudjoe Key

Cudjoe Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £154 / night

£1,078 / week

1 / 14

Holiday home in Marathon

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £574 / night

£4,013 / week

1 / 30

Tavernier holiday home rental

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £299 / night

£2,089 / week

1 / 22

Ski villa to rent in Duck Key

Duck Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £461 / night

£3,226 / week

1 / 26

Cottage rental in Cudjoe Key

Cudjoe Key cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £293 / night

£2,050 / week

1 / 30

Marathon ski villa to rent.

Marathon villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £468 / night

£3,271 / week

1 / 30

Holiday home in Tavernier

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £332 / night

£2,320 / week

1 / 30

Holiday cottage rental

Cudjoe Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £186 / night

£1,303 / week

1 / 10

Ski condo to rent in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £289 / night

£2,023 / week

1 / 24

Holiday home in Tavernier

Tavernier house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £659 / night

£4,612 / week

1 / 30

Condo rental in Tavernier

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £217 / night

£1,517 / week

1 / 29

Ski condo to rent in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £226 / night

£1,578 / week

1 / 30

Cudjoe Key holiday home rental

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £287 / night

£2,007 / week

1 / 19

Cottage accommodation in Cudjoe Key

Cudjoe Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £258 / night

£1,801 / week

1 / 9

Ski cottage to rent in Cudjoe Key

Cudjoe Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £238 / night

£1,660 / week

1 / 29

Cudjoe Key holiday cottage rental

Cudjoe Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £204 / night

£1,424 / week

1 / 20

Pigeon Key holiday home rental

Pigeon Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 2

from £111 / night

£774 / week

1 / 17

Holiday condo in Tavernier

Tavernier condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £497 / night

£3,480 / week

1 / 30

Holiday home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £200 / night

£1,396 / week

1 / 23

Condo rental in Tavernier

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £206 / night

£1,440 / week

1 / 24

Home accommodation in Marathon

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £462 / night

£3,232 / week

1 / 30

Holiday cottage in Cudjoe Key

Cudjoe Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £251 / night

£1,757 / week

1 / 11

Ski cottage to rent in Marathon

Marathon cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £334 / night

£2,337 / week

1 / 30

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Florida Keys holidays

Florida Keys, FL, including the islands of Key West, Key Largo, Islamorada, Marathon Key and Big Pine Key offers the perfect mix of family beach fun and peaceful holiday relaxation. Spend your days strolling one of the many boardwalks, or swim, snorkel, and kayak in the pristine Gulf. After a long day, retreat back to your holiday rental home at night, escape the crowds, and watch the sunset across the Gulf from your personal porch or deck. With your own private tennis court and pool, luxuries that many rentals offer, you can have a great time without even leaving your holiday home.

Wake up to the sound of waves rolling in and the scent of the salty ocean air, then walk just minutes to the beach for great boardwalk shopping, dining, and entertainment. Truly escape the winter chill by heading to the southernmost point in the United States, Key West, Florida. Take U.S. Highway 1, known to locals as "The Overseas Highway" to get there, and enjoy the breath-taking natural beauty of the ocean scenery and wilderness that borders the road.

Here are a few additional suggestions for your trip to the Florida Keys:

  • Visit the Key West Butterfly & Nature Conservatory: Key West is home to a magnificent array of butterflies from South America, Africa, and Southeast Asia. This Conservatory emphasises the importance of wildlife preservation, offering group tours, unique films, and resident rainforest birds guaranteed to ignight your love for wildlife.
  • Swim with the dolphins: Key West is known for its dolphin friendly environment and facilities that offer guests the opportunity to swim and play with these amazing animals.
  • Explore The Harry S. Truman Little White House: Established in 1890 as a command centre during the Spanish American War, this house was later used as a means of escape during the Cold War. For years, presidents relaxed and restored body and mind here while dealing with war threats. The site is now a living history museum.
  • Sleep under the stars: Spend a night under the legendary stars of Key West. Florida Keys campgrounds are plentiful, and Florida Keys camping can also happen at sea. Charter a boat and drift off with the night sky above and the ocean below.
  • Take a sunset dinner cruise: Gourmet dinner cruises to Florida Keys' destinations are widely available. Nothing is more romantic than raising a glass on a luxury sailboat as the sun sets over the Atlantic.
  • Take a charter fishing trip: An experienced outfitter can provide the boat and equipment you need to pursue deep water species like marlin and swordfish.

Whether you're here for a Florida Keys honeymoon, a family reunion, or a holiday getaway with friends, you'll easily find a perfect holiday rental with all the amenities you need to relax in style. Stay in a charming beach condo close to the restaurants and nightlife or rent an elegant villa with a balcony and stunning views of the ocean. You may also want to make some time during your holiday to visit nearby destinations like Naples or Marco Island.

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