There comes a time when you need to recharge the batteries. Relax. We don’t write the prescription, but we do have the medicine! At the Outpost Islamorada, whether it’s a vacation or special event, a business conference or a day of sales calls, we offer every opportunity to relax and unwind.



Oceanside, the resort features two swimming pools, both perched beachside in the center of the action. The larger freshwater oasis pool includes an inviting Jacuzzi, tucked away in the side of the large pool deck. On an upper deck a saltwater pool sits aside the pool grill, a reminder that a day by the pool isn’t complete without fabulous poolside food and beverage service.


Bayside, the resort features an elegant freshwater pool overlooking the calm waters of Florida Bay, with the feel of your own private retreat.By the way, our pools are heated, as every once in a while it gets chilly and we’re not about to let that ruin your day!



The islands are small and the opportunities are few for major beachfront settings in the Florida Keys. Well, at the Islander we have one of the largest, with our shoreline running over two tenths of a mile. That’s a lot of palm trees and beach to find the perfect spot for sunbathing in the sand.


Our pools are always nearby, and of course, we have lounge chairs there too to serve your needs. Sometimes, it’s just no more complicated than grabbing a lounge chair outside your unit. Catch a nap or grab some rays…your choice. It’s your vacation, not ours!



We admit that our fitness center is not the largest around, as we’ve found most our guests are up at dawn intending to burn calories out on the water. For the rest of our guests, our fitness room includes a treadmills, bicycles, a complement of free weights and TV for entertainment.

Fishing Pier


Few activities are more relaxing that leaning against the rail of a pier, staring out to the horizon or simply looking down and watching your own private marine theater. Enjoy our lighted pier that stretches out into the water almost the length of a football field. You can even grab your fishing rod and try your luck, no permit required! Really, who needs a boat?



We can’t do it better than our friends at Blue Bamboo Salon and Spa, located just next door to the Outpost Islamorada Oceanside. Whether a day of pampering, a quick cut and blow dry, manicure, pedicure or complete wedding day services, you’ll find a staff that is seriously dedicated to a level of customer service that may turn you into a permanent resident of Islamorada. To learn more, click here.

Artist and Boutiques


Visit our friends at the Morada Way Arts & Cultural District, a non-profit arts and cultural organization in Islamorada, Florida Keys — with classes, demonstrations, expos & ArtWalks!

ArtWalks are held on the THIRD THURSDAY of every month throughout the year, offering extensive art exhibits, live music, food, drinks, shopping, and other fun activities. Drawing thousands of people each month, this event has become the talk of the Keys. The crowds stroll through the Art District, which spans one-half mile of the Old Highway between the historical 1935 Hurricane Monument and the iconic Green Turtle Inn and includes the intersecting street now known as Morada Way. It is less than a mile away from the hotel but check with the Guy Harvey Outpost Outfitter in the lobby for the free trolley ride over.