About Resort

Located at mile marker 82, the Islander Resort, Guy Harvey Outpost is roughly halfway between the Miami Airport and Key West, in the heart of the Florida Keys.

Billing itself as the “Sport-fishing Capital of America”, Islamorada is a dream vacation destination. Outpost Islamorada offers the best of keys lodging options, from sunrise beach views of the Atlantic to sunset marina views of the Gulf of Mexico and Florida Bay.

Islander Resort, a Guy Harvey Outpost

The Islander Resort, a Guy Harvey Outpost is the quintessential Florida Keys hideway resort and well-known for its iconic enterance sign projecting out over AIA. With a mere 114 guestrooms spread out accross 25 acres and one the largest beachfronts to be had in all of the Keys, the Islander Oceanside is an oasis of casual relaxation. No stairs, no elevators – all single-story bunglows set under the shade of towering palm trees, with two oceanfront pools and patios to soak up the sun, sea & skies.

Catch a great breakfast at Bonefish Flats, and don’t miss the culinary specials of our open-air waterfront pool grill, soon to become “Guys Beachside Bar & Grill”.

If you’re planning a meeting or special event, we’ve just opened our new state-of-the-art conference center with its spectacular ballroom and pre-function patio areas overlooking the Atlantic Ocean.

All rooms and suites at the Islander Oceanside come fully equipped with kitchens, including refrigerators, stove tops and dish washers! Daily housekeeping ensures your vacation is truly a vacation from the daily chores back home of cooking and cleaning.

Islander Bayside, a Guy Harvey Outpost

Located at Mile Market 81.5 Bayside accommodations sit overlooking Florida Bay and our marina basin, directly across from the legendary Islamorada restaurant, Sid ‘N Roxies Green Turtle Inn. Enjoy time in your private retreat with each having a view over the marina basin and beyond to Florida Bay and its magnificent sunsets. The Bayside accommodations are all two bedroom townhomes featuring a full kitchen, living room and patio. Whether your boat’s out back or not, whether you’re entertaining the family or hiding out while writing the next great American novel, the million-dollar sunset views are yours at no extra charge!

For the boater, the marina is at the front door to the one of the last great wilderness areas, the Everglades. Our 14-slip marina is perfect for the boater or angler towing his boat to the keys for some time cruising of fishing the Florida Keys. We can accommodate boats up to 24 feet, which draw up to 3 feet. If you have a boat above 24 feet just let us know and we can recommend a nearby marina. Dockage rate is $25/day and we offer discounts for long term stays!

We operate Islander Bayside much like a private community within a resort. Enjoy the peace and calm of a self-catered retreat, yet access and use of all the facilities at the main resort, Islander Oceanside. If you plan on cooking, or want a mini-bar the size of your kitchen back home, let us help you stock the pantry prior to arrival if you wish, or we’ll give you recommendations on your arrivals. Islamorada has any number of shopping options for any taste or budget. Feel comfortable bringing your cooler and groceries. This is your vacation. This is your home away from home.