Hip Hotels in Florida Keys

Popular Places

  • Islamorada
  • Marathon Key
  • Pennekamp State Park
  • Little Palm Resort

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    28500 Overseas Hwy
    Florida Keys

    Peaceful tropical island retreat... read more

    The Moorings Village

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    123 Beach Road

    Private cottages on 18 acres... read more

    Hawk's Cay Resort

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    61 Hawk's Cay Boulevard
    At MM 61

    Family-oriented casual resort... read more

    Casa Thorn

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    114 Palm Lane

    Secluded getaway... read more

    Cheeca Lodge & Spa

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    81801 Overseas Highway, Mile Marker 82
    Marker 82

    Oceanfront, tropical resort with secluded beach, 525-foot pier... read more

    Holiday Isle Resort

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    84001 Overseas Hwy
    U.S. 1 at MM 84

    Lively, beachside partying atmosphere for young, hip travelers... read more

    The Marquesa Hotel

    600 Fleming Street

    Key West's finest small hotel & café in the historic district... read more

    Chesapeake Beach Resort

    83409 Overseas Hwy

    Oceanfront resort for fishing and private beachgoers... read more



    Upscale, secluded suite hotel, arrive by car or boat... read more

    Deer Run Bed & Breakfast

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    Long Beach Road

    Exclusive Beach Hideaway... read more

    Jules Undersea Lodge

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    51 Shoreland Drive

    Former underwater research lab... read more

    Banana Bay Resort & Marina

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    4590 Overseas Highway

    Lush tropical resort spans 10 acres overlooking Florida Bay... read more

    White Gate Court

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    P.O Box 1528, 76010 Overseas Highway
    Lower Matecumbe

    Small Gulf side resort... read more

    Kona Kai Resort & Gallery

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    97802 Overseas Highway

    Art works in the lobby... read more

    Old Wooden Bridge Guest Cottages & Marina

    1791 Bogie Drive

    Pet friendly efficiency cottages on the bay and ocean... read more

    The Tavernier Inn

    91865 Overseas Highway

    A member of the Keys Caribbean family of vacation resorts... read more

    Casa Morada

    136 Madeira Road

    Indigo Bay Hotel

    81450 Overseas Highway

    Luxury cottage-style condo accommodations... read more

    Amy Slate's Amoray Dive Resort

    104250 Overseas Highway

    Dive Pennekamp, Spiegel, Duane and more. On-site resort to stay where you dive... read more

    Sea Dell Motel

    5000 Overseas Highway

    Newly remodeled "Old Keys" style rooms with refrigerators, microwaves, and coffeemakers... read more
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