Hotel Review • North America • United States • Florida • Florida Keys • Islamorada

Islander Resort: A Tranquil Island Retreat In the Florida Keys

Plan your getaway to Islander Resort in Islamorada. Explore this tranquil 24-acre oceanfront retreat in the Florida Keys featuring chic bungalows and fresh seafood.

Courtesy of Islander Resort

BY SUSAN B. BARNES

Why it works

Hotel Snapshot

In the early 1900s, railroad pioneer Henry Flagler's exclusive fishing camp lured the wealthy elite to Islamorada in the Florida Keys, accessible via his rail line to Key West, the southernmost point of the continental U.S. After a devastating hurricane destroyed the fishing camp in 1935, the land sat dormant until an attorney and avid fisherman built the Islander Resort in 1951.

Fast forward 75 years, and travelers who venture along the Overseas Highway to Islamorada, the Sport Fishing Capital of the World, will find the recently reimagined resort’s tranquil grounds cascading across 24 oceanfront acres, not to mention their personal slice of island paradise.

Design & Character

Islander Resort’s 1950s “Space Age” sign at its foliage-lined entrance provides guests with their first glimpses of the Mid-Century Modern–meets-island-chic aesthetic they will enjoy during their stay, beginning with check-in at the Main House. The resort’s open-air design flows like the trade winds: no two buildings are connected, and guests meander along landscaped, sandy paths from their accommodations to restaurants, beachfront activities, watersports, and the pier, an idyllic spot for sunrise or sunset.

The Rooms

The hotel has 114 recently redesigned guestrooms, suites, and bungalows dotting the grounds, and 25 newly reimagined two-bedroom, townhome-style Bayside Villas. Interiors are designed to prioritize calm and comfort: think crisp whites, warm creams, and soft greens and blues accented with blonde woods, wicker, rattan, and tile floors. Sliding glass doors and expansive windows invite the Florida sunshine to stream in, or stylish shutters keep it out. The bungalows’ private furnished patios provide an easy indoor-outdoor flow, as do the villas’ private decks.

The Plumeria Ocean Front Suite boasts a living room, king-size bedroom, private covered patio with a hammock for swaying in the warm breezes, and a full kitchen, ideal for longer stays.

The Food & Drink

Island vibes continue to flow at each of the resort’s on-site, open-air restaurants and bars, from morning until night, from the casual Coccoloba, Tides Beachside Bar and Sandy’s Bar, to Drift on the Beach for more traditional dining. Unsurprisingly, fresh seafood takes center stage on the restaurants’ menus here in the Sport Fishing Capital of the World. The bouillabaisse with yellowtail snapper, scallops, shrimp, mussels, and clams is a must, as is the Florida lobster pasta, both served at Drift. Weekends call for Veuve Clicquot Brunch.

Amenities

The Islander provides everything guests could want during an island stay, whether simply basking in the warm sun at the pool or oceanfront, or filling their days with adventure. For the active traveler, there is pickleball, beach volleyball, basketball, bocce ball, a putting course, fishing from the pier, kayaking, and stand-up paddling right on the resort’s grounds. Or plan a fishing charter or snorkel tour for a more aquatic adventure. Laid-back options include complimentary yoga classes, sunset catamaran sails, and private pool cabanas. The resort also hosts a variety of activities, such as poolside movie nights, game clubs, kite flying, bonfires and s’mores, and more.

Location & Neighborhood Recs

Islamorada, known as a village of six islands, sits halfway between Miami and Key West, about 80 miles from each. Learn about local history at the Florida Keys History and Discovery Center on Islander Resort’s grounds; take an eco-tour and paddle through the mangroves while keeping an eye out for manatees and dolphins; or dive into the deep blue and spend time with undersea creatures. Don't miss feeding the tarpon at Robbie’s of Islamorada.

Fast Facts

Address: 82100 Overseas Highway, Islamorada, FL (Mile Marker 82.1)

Neighborhood: Florida Keys

Nearest Airport: Miami International Airport (80 miles), Key West International Airport (80 miles)

Star Rating: 4 stars

Room Count: 139 guest rooms, suites, and villas

Vibe: A casually elegant oceanfront retreat where guests feel their cares float away with the warm trade winds.

Best For: Anyone looking for a getaway from the real world, whether traveling solo, with a partner, or with friends or family.

Amenities: Four on-site restaurants and bars, beachfront and water activities, 24-hour fitness center, self-parking, pet-friendly.

Nearby: Florida Keys History and Discovery Center, Alligator Reef Lighthouse, Robbie’s of Islamorada, History of Diving Museum

Our Favorite Thing: The resort is pet-friendly, so guests’ four-legged family members can tag along for the island fun

Gallery

A closer look

Courtesy of Islander Resort

Courtesy of Islander Resort

Courtesy of Islander Resort

Courtesy of Islander Resort

Courtesy of Islander Resort

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