Best Resorts in Islamorada

U.S. News ranks the best resorts by taking into account reputation among professional travel... READ MORE
U.S. News ranks the best resorts by taking into account reputation among professional travel experts, guest reviews and hotel class ratings. Use the filters and settings below to help find the best resort for you.

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Hotel Name
Price

$1 - $500+

Hotel Class

1 star - 5 stars

Amenities

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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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    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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    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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    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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