Tranquilo y Tropical

South of Miami, down a one-way road that winds through swamp and sea, lies a little slice of paradise: Islamorada. A constellation of six small islands that make up the heart of the Florida Keys, Islamorada is where locals go to get away and travelers from all over the world venture to in pursuit of the same – tranquilo y tropical. That deliciously slow, serene island life. 

Here in Islamorada, the days are decidedly carefree and almost always spent on the water. With the Gulf of Mexico on one side and the Atlantic Ocean on the other, you’re spoiled for choice of aquatic adventures. There’s trophy fish to reel, coral reefs to snorkel, mangroves to kayak, and much, much more. And when the sun sinks into the horizon, the fun is just getting started. There’s live music in tiki bars, a vibrant downtown filled with art and boutiques, freshly caught seafood and ice cold beer, full moon parties, and night fishing under the stars.

Whether you want to do it all, or nothing at all, there’s no better place to embrace Islamorada’s island life than the iconic Islander Resort and Bayside Villas by Islander Resort. 

Stretching across 24 acres, the Islander Resort and its sister property, Bayside Villas by Islander Resort, are as secluded as they are scenic. But finding your way here is easier than you think. Just look for the historic retro sign at mile marker 82, and paradise is found.

There are seemingly endless things to do at the Islander Resort. In addition to its saltwater pools, beach volleyball court, rental bikes and walking trails, the oceanfront resort offers a range of on-site water sports like kayaks, paddleboards, snorkeling, and more. 

In partnership with Islander Girl Tours – a local, women-owned, women-led business from the Florida Keys – the resort also offers scuba diving, snorkel tours, group swims to Islamorada’s famous sandbar, sunset cruises, private boat charters, and equipment rentals for glass-bottom kayaks and hydro bikes.

Craving some R&R instead? Lazing the day away is equally encouraged here. Sprawl out oceanside on the Islander’s coral sand beach, sip a cocktail by the pool, stroll the butterfly garden, or curl up in a hammock for an afternoon read by the sea.

When it’s time to retreat from the Florida sunshine, you won’t have to go far – the Islander’s 114 guestrooms and suites are just a quick walk from its private beach.

Whether you’re traveling as a couple, a couple of couples, or a big ‘ol family, Islander Resort has accommodations to suit every style – from studio-style rooms with tropical garden views to oceanside suites with gourmet kitchens and personal hot tubs. 

Bayside Villas by Islander Resort are perfect vacation rentals in Islamorada for guests who want the comforts of home for a short or long stay. Here you’ll find luxurious, residence-style villas complete with full kitchens and private decks. Villa guests enjoy exclusive access to rent the on-site boat slips and a beautiful bay view pool.  Bayside Villa guests also have full access to all the action, activities, amenities and dining at Islander Resort.

The Florida Keys are known for beach-bar style dining, but throughout Islamorada you’ll find delicious spots across a spectrum of casual seafood joints and upscale restaurants, almost all with water views. 

At Islander Resort’s Tides Beachside Bar & Grill, kick back for lunch by the water and savor fresh seafood with a tropical drink in hand. Choose from dishes like tuna crudo, corvina ceviche and mango shrimp, or indulge in a decadent truffle burger and lobster truffle mac ‘n’ cheese instead. Add Elements Lounge here. At the Islander’s Elements Lounge & Restaurant, even more seafood awaits. This sophisticated, Caribbean-inspired eatery offers a delectable menu of locally caught, “pier to plate” seafood and inventive island fare served oceanside. 

Thanks to the resorts’ prime location, guests are a quick drive or bike ride away from locally-loved Islamorada staples too. Check out the Green Turtle Inn for breakfast, Chef Michael’s, Square Grouper or Ziggie and Mad Dogs for a fancy dinner, and Hog’s Heaven for a rowdy night out. Beer lovers should also plan for pit stops at Florida Keys Brewing Co. and Islamorada Beer Company, cheery local breweries with live music and indoor/outdoor seating. 

When the sun finally sets on your Islamorada adventure, don’t rush home just yet. Overseas Highway, the one-way road back to mainland, is dotted with kitschy mom ‘n’ pop shops, art galleries, and local bakeries boasting the best key lime pie around. Pull over to explore whatever catches your eye, and bring some tranquilo y tropical home with you. After all, island life is a state of mind. 

Ready to embrace the Islander life? Book your stay at least 7 days prior to arrival and enjoy 15% off our best available rates at Islander Resort or Bayside Villas by Islander Resort.