Islander Resort on Islamorada in the Florida Keys is a prime example of ‘adaptive reuse’ done right over the course of more than a century.
Adaptive reuse is gaining momentum in the hospitality industry, with a focus on renovating older, historic properties, rather than demolition. This approach enables the preservation of history, while also providing guests with the modern experiences they desire.
Islander Resort has stood the test of time (and nature). It has persisted as a beloved establishment on Islamorada since 1951, when it was established along 1,100 feet of coral sand shoreline.
A History of Resilience and Reinvention
The property began as an exclusive fishing camp accessible via railroad in the early 1900s, hosting guests such as the Rockefellers. After a hurricane destroyed the camp in 1935, fisherman and attorney Leo Samuels established Islander Resort, with its signature mid-century modern aesthetic and a vision for creating a relaxing, family-focused escape in 1951.
In 1999, Islander Resort entered a new chapter under the ownership of David Curry, with a focus on supporting the natural ecosystem, instituting recycling initiatives, native landscaping, and underground utilities.
More recently, Islander Resort was further ushered into the modern era with an extensive renovation in 2025, now offering 114 elevated bungalows and suites with modern comforts and thoughtful touches while preserving the hotel’s mid-century modern charm.
The Accommodations & Amenities
In Islander Resort’s bungalows, you will find plush robes and slippers, dreamy beds, a modernized bathroom, and a Nespresso machine for your morning coffee that you can enjoy on your private patio with views of the pool or ocean. The decor design is thoughtful, lively, and modern.
They did not miss any opportunity to show they care about the small details, with fun touches like tropical wallpaper brightening up your room’s closet. The hotel has maintained its single-level hotel room layout, honoring its 1950s roots, and offering a private and relaxed atmosphere.
Throughout the resort grounds, they created countless places you can relax and soak up the elevated amenities and water views. Whether you prefer a plush lounge chair, a couch sectional surrounding their fire pits, or swinging seats with water views, there are numerous places to unwind and connect with friends and family.
One of the most remarkable aspects of Islander Resort is the relaxed atmosphere that prevails among both guests and staff. Here, things are slower in the best way, and you have a chance to decompress from the usual business of life.
If you are looking for two-bedroom townhouse-style accommodations for larger groups, you can stay at Islander Resort’s Bayside Villas. This separate, but close-by, property features 25 villas, bayside pool access, water sports, rental boat slips, and full access to Islander Resort’s oceanside resort amenities.
Relax in the Sun with Water Views
Guests will find two pools on the main resort grounds that honor the mid-century modern roots of the hotel with their retro shape and details. Here you can find elevated seating and tropical landscaping, with relaxing views of the water.
Islander Resort focuses on the small details that really enhance the guest experience, offering complimentary refreshing treats by the pool and oceanfront, such as frozen watermelon slices, fresh coconut water (straight from the tapped coconut), and frozen fruit drinks.
You can also rent a pool or ocean view cabana, where you can relax on plush cabana chairs and enjoy dedicated food and drink service, including a complimentary fresh fruit plate and wine. The Tides kitchen serves the crispiest and most satisfying fries, making them a perfect cabana snack to enjoy alongside your wine.
These cabanas are ideal for Saturdays, when the property can get slightly busier with day passes.
Islander Resort’s Food Scene
Tides Beachside Bar is the perfect spot for a casual and delicious meal with water views, offering seating at the bar, pool, and beach. Here you can find vibrant salads, signature pizzas, fresh-caught seafood, classic sandwiches, and fresh cocktails (including your favorite tropical classics), alongside live music.
Their spicy palomas, pizza of the day, and shoreline salad, featuring strawberries, fennel, almonds, and feta with a honey white balsamic vinaigrette, are must-haves. Additionally, their orange tuna salad, featuring macadamia-encrusted seared tuna, pickled shallot, charred heirloom tomato, and miso orange vinaigrette, is also a must-try.
Tides’ poolside brunch service is also a great way to soak up Islander Resort experience. You can find breakfast classics such as Eggs Benedict and cheesy omelettes with the best breakfast potato wedges.
For a classic tropical bar and snack experience, you can stop by Sandy’s Bar and Coccoloba on the oceanfront beach area. They have fun, tiki-inspired seating areas with swinging chairs, long tables, and small nooks where you can enjoy your drinks and snacks in groups of all sizes.
Be sure to try a rum runner cocktail at Sandy’s Bar to soak up an authentic Keys experience, and grab some fresh chips and guacamole from Coccoloba to enjoy on the lounge chairs overlooking the ocean.
Islander Resort’s restaurant, Drift on the Beach, offers a beautifully curated, coastal-inspired food and drink menu alongside a peaceful view of the ocean. This spot focuses on locally sourced, fresh ingredients and cooks their dishes over an open flame. Their drink menu pays homage to the Florida Keys’ rum-running history with carefully crafted cocktails, complemented by a diverse global wine selection.
Some must-try dishes include their coconut ceviche, featuring the day’s fresh catch, shrimp, spiny lobster, and chili ginger coconut milk; the vine tomato and burrata plate with arugula and peach vinaigrette; the clay pot chicken with kaffir lime coconut broth; and the key lime tart with toasted meringue.
By far the best spot for after-dinner drinks is by one of Islander Resort’s waterfront fire pits. You can grab a glass of wine or a cocktail from the Tides Beachside Bar and relax in the sea breeze and firelight.
Complimentary Activities for All
There is no shortage of activities for everyone to enjoy. Islander Resort has complimentary Seaside Sports, including mini golf, pickleball, bocce ball, kayaking, and more.
You can even experience complimentary yoga classes, offered every Wednesday, Thursday, Friday, and Sunday morning. This is such a great way to truly unwind on your vacation and start the day off relaxed and refreshed.
Guests can also enjoy a daily Seabreeze Social with sangria and spritzers in the Shoreline Cabana, a poolside movie night each Friday at the Oasis Pool, nighttime mini golf with neon lights on Friday and Saturday evenings, and the Islander Game Club on Saturday afternoons at Tides Beachside Bar.
An Authentic Florida Keys Escape
Islander Resort offers both a down-to-earth and elevated experience that is true to its mid-century roots, making it a classic Florida Keys getaway.
With its modernized suites and amenities, flavorful culinary options, and beautiful views of the water, you are sure to unwind completely and experience an authentic piece of Florida Keys history.
