Best Hotels in Islamorada

U.S. News & World Report ranks the best hotels in Islamorada based on an analysis of industry... READ MORE
U.S. News & World Report ranks the best hotels in Islamorada based on an analysis of industry awards, hotel star ratings and user ratings. Hotels that scored in the top 10 percent of the Best Hotels in the USA earned a Gold badge. Hotels that appear after ranked hotels are sorted by hotel class and then by user rating, as provided by TripAdvisor.

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12 matches

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Hotel Name
Price

$1 - $500+

Hotel Class

1 star - 5 stars

Amenities

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12 matches
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    Cheeca Lodge & Spa
    Islamorada, FL
    $45 Nightly Resort Fee
    4.0-star Hotel Class
    4.0-star Hotel Class
    $45 Nightly Resort Fee
    • Free Parking

    • Free WiFi

    The Cheeca Lodge & Spa sits pretty on the skinny Florida key known as Upper Matecumbe, part of an incorporated village of islands called Islamorada. Travelers love this resort because it achieves a tropical getaway. But some mean this in a good way (transparent waters, calm Florida Bay breezes), while others mean this as an insult (too tropical to keep all the bugs away). There are several perks to staying at Cheeca Lodge, however. For one, the rooms feature screened-in balconies and rain showers, as well as flat-screen TVs, Illy espresso machines and wireless internet access (which is covered by the daily resort fee). Another plus, the bungalow-like setting is supremely romantic, and families will like that some of the accommodations have kitchens. If you don't feel like cooking, you can sit down to dinner at one of four on-site restaurants, which serve up fresh seafood and other tasty entrees. You'll find the Cheeca Lodge & Spa about 86 miles southwest of Miami and 80 miles northeast of Key West.
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    Amara Cay Resort
    Islamorada, FL
    3.5-star Hotel Class
    3.5-star Hotel Class
    • Free WiFi

    The oceanfront Amara Cay Resort is in the heart of the Florida Keys on the southern end of the town of Islamorada, which is home to shops, restaurants and the informative Keys History & Discovery Center. The beachy lobby features hanging basket chairs and driftwood accents, and its guestrooms and suites have neutral color schemes with seafoam and rattan accents. All rooms come with bathrobes and slippers, TVs with premium channels and rainfall showerheads in the bathroom; most rooms also have balconies. There’s daily resort fee that includes access to the fitness center, Wi-Fi, parking, use of beach chairs and towels, a shuttle into town and bike, kayak and paddleboard rentals. The hotel’s tiki bar, Reelburger, serves cocktails, milkshakes, fries and burgers for lunch and dinner by the free-form saltwater pool. Note that there is no late-night dining option or room service available at this pet-friendly resort.
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    Fisher Inn Resort & Marina
    Islamorada, FL
    3.5-star Hotel Class
    3.5-star Hotel Class
    • Free WiFi

    Fisher Inn Resort & Marina is a 3.5 star hotel located at 84951 Overseas Highway in Islamorada. It has a 4.5 overall guest rating based on 83 reviews.
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    Topsider Resort
    Islamorada, FL
    3.5-star Hotel Class
    3.5-star Hotel Class
    Topsider Resort is a 3.5 star hotel located at 75500 Overseas Hwy in Islamorada. It has a 4.0 overall guest rating based on 62 reviews.
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    Casa Morada
    Islamorada, FL
    3.5-star Hotel Class
    3.5-star Hotel Class
    • Free WiFi

    Casa Morada is a 3.5 star hotel located at 136 Madeira Road in Islamorada. It has a 4.5 overall guest rating based on 1137 reviews.
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    The Moorings Village
    Islamorada, FL

    No confirmed availability on selected dates.

    3.5-star Hotel Class
    3.5-star Hotel Class
    • Free WiFi

    No confirmed availability on selected dates.

    The Moorings Village is a 3.5 star hotel located at 123 Beach Rd in Islamorada.
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    Islander Resort, a Guy Harvey Outpost
    Islamorada, FL
    3.0-star Hotel Class
    3.0-star Hotel Class
    • Free WiFi

    Islander Resort, a Guy Harvey Outpost is a 3 star hotel located at 82100 Overseas Highway in Islamorada. It has a 4.5 overall guest rating based on 370 reviews.
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    Pelican Cove Resort & Marina
    Islamorada, FL
    3.0-star Hotel Class
    3.0-star Hotel Class

    A beachfront resort in Islamorada, Florida, Pelican Cove Resort & Marina offers a spectacular vantage point for visitors to enjoy the beauty of the Florida Keys. Guests will have no shortage of things to do on-site with an outdoor pool, a saltwater lagoon, a private beach, and a marina to explore. Particularly adventurous guests can participate in water sports and fishing. After they’ve tired themselves out, this resort has a restaurant and a cafe to refuel. (There is also a Starbucks relatively close.) The property recently renovated each of its 63 guest rooms with contemporary, clean decor, plus a flat-screen TV, a coffee maker, a minifridge, a private balcony and complimentary internet access. Recent guests rave about the spectacular views, helpful staff and multiple activities. Despite these pros, some visitors suggest that a few furniture pieces in the rooms prove to be more fashionable than comfortable. 

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    La Siesta Resort & Marina
    Islamorada, FL
    3.0-star Hotel Class
    3.0-star Hotel Class
    • Free WiFi

    La Siesta Resort & Marina is a 3 star hotel located at 80241 Overseas Highway in Islamorada. It has a 4.0 overall guest rating based on 791 reviews.
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    Postcard Inn Beach Resort & Marina
    Islamorada, FL
    3.0-star Hotel Class
    3.0-star Hotel Class
    • Free WiFi

    Postcard Inn Beach Resort & Marina is a retro, beachfront hotel that still manages to offer the contemporary perks travelers expect. The property’s location allows guests to access the breathtaking waters that surround the island of Islamorada. The accommodations at this hotel blend nostalgic decor with modern amenities, offering complimentary Wi-Fi access, flat-screen TVs and iPod docks in each of the 143 guest rooms. Plus, lodging options have extra perks like a private, furnished balcony with a marina view. There is a lot to do on-site, with a private beach, a resort-style outdoor pool, and diving and snorkeling trips, as well as other water sports. Recent guests love that everything food and fun related is nearby, with recreation, a raw bar, a restaurant and a Tiki bar all on-site. Travelers can’t help but bemoan the daily resort fee though. 

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    Pines & Palms Resort
    Islamorada, FL

    No confirmed availability on selected dates.

    3.0-star Hotel Class
    3.0-star Hotel Class
    • Free WiFi

    No confirmed availability on selected dates.

    Pines & Palms Resort is a 3 star hotel located at 80401 Old Hwy in Islamorada.
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    Chesapeake Beach Resort
    Islamorada, FL
    2.5-star Hotel Class
    2.5-star Hotel Class
    • Free WiFi

    Chesapeake Beach Resort is a 2.5 star hotel located at 83409 Overseas Hwy in Islamorada. It has a 3.5 overall guest rating based on 785 reviews.

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