The perfect Florida Keys vacation getaway and sport fishing destination, Islander Resort, the newest Resort, is ideal for vacationing with friends and family, as well as the perfect spot for a wedding, a romantic getaway or believe it or not, a business meeting.
Islamorada gives you the best in boating, fishing, diving and dining. Islander Resort, ’s Outpost Islamorada, brings you the best lounging and living the Florida Keys has to offer. The Islamorada Outpost features two waterfront resorts and offers you the choice of sunrise or sunset views.
Our two Florida Keys resort properties give you the perfect resort accommodation options for spending a long weekend or a long winter. Our beautiful oceanfront resort boasts a new conference center, a pristine private beach, as well as two oceanfront swimming pools, a hot tub, shuffleboard, volleyball and a lighted, 200-foot fishing pier with amazing views of local marine life. It is the home of Guy’s Beachside Bar & Grill. Our self-catering bayside townhomes feature fully equipped gourmet kitchens, a gulf front pool, beach, picnic area and a 14-slip marina basin. All Islander accommodations offer full kitchens and complimentary wireless internet. We never charge resort fees.
Islander Watersports and the Outfitter believe every great vacation involves time in the water and on the water. Let us be your guide to excitement, entertainment and activities of all kinds. From catching the big one to booking a massage or making a dinner reservation, vacation experts are standing by – email now and start dreaming.
Islander Resort, is also home to the Florida Keys Conference Center. If you are looking for unconventional meeting or event space, you’ve found the perfect destination. Our state-of-the art meeting facility offers the ideal combination of indoor functionality and outdoor oceanfront beauty. From beachfront to ballroom, let us help you plan the perfect beach wedding or a truly motivating incentive meeting.
As part of the family, we offer all of our guests the opportunity to join the Hammerhead Nation. “Hammerheads” are the legions of fans who have fully adopted the lifestyle. Hammerheads share Guy’s passion for angling, diving, boating and travel – a life full of adventure and exploration balanced by a keen interest in conserving the marine environment.
The Oupost brand was created to be a collection of properties in unique destinations, like islander Resort and Islamorada, owned and staffed by people who are passionate about their time on, in and around the water. We want to create a recreational product that exemplifies the type of experiences that Guy himself enjoys in his own travels, where each trip is an adventure – an expedition of discovery, with experiences that become memories to last a lifetime.
Leave your cares behind and escape to the beauty of the fabulous Florida Keys, America’s Caribbean Islands. Known as the “Sportfishing Capital of the World,” Islamorada is the perfect blend of oceanfront elegance, unspoiled nature and Floribbean style. Islamorada in the Florida Keys is the perfect location for Islander Resort, the newest a Florida Keys paradise that offers guests a taste of the good life in a casual, island atmosphere.
An amazing 22 acre Atlantic Oceanfront resort or an intimate Gulf front condo-hotel featuring 25 luxury townhomes and marina basin. Oceanfront lounge chairs or gulf side dock, the choice is yours at Islander Resort,.
As we say at ,
“From the Oceans, Comes Life, Enjoy the Journey