The Islander Resort: The gem of Islamorada
If Islamorada is the soul of the Florida Keys, The Islander Resort is its front porch. 22 acres, 1,100 feet of white sand beach, and that perfect old-Florida-meets-new-luxury feeling that you cannot fake. This is not a high-rise hotel where you never meet your neighbor. This is a true Keys beach resort.
After multiple stays, I can say this is the place I send friends to when they want to actually experience Islamorada, not just sleep there.
First Impression & The Property
You pull off Overseas Highway at Mile Marker 82.1 Oceanside and the classic 1950s blue-and-white Islander sign is still there, manatee mailbox and all. The resort was badly damaged in Hurricane Irma in 2017, and they used it as a chance to completely reimagine it. It’s now in its “New Era” and it shows. The grounds are immaculate – lush tropical landscaping everywhere, swaying palms, paved pathways lit at night, hammocks strung between trees, charcoal grills and picnic tables tucked into little private nooks. It feels private, not crowded, even with 114 rooms.
The Rooms: Actual Beach Cottages
Every single one of the 114 rooms and suites has a screened-in private patio, air conditioning, vaulted ceilings, and a kitchenette or FULL kitchen with full-size fridge, dishwasher, oven, and dining table. Many have private outdoor picnic tables + grill. You park literally right outside your door. No long hallways, no elevators. The beds are comfortable, the rooms are spotless, hooks everywhere for wet bathing suits, and the ocean view from the bungalows is spectacular. Pet-friendly and genuinely welcoming to dogs.
The Beach & Pools – The Heart of the Resort
The Islander has one of the largest beaches in all of Islamorada – wide, white, raked daily, with tons of lounge chairs. Then you have TWO beachfront pools – one freshwater, one saltwater – plus a hot tub tucked away. Poolside drink service is fast and friendly.
Plus: 600-foot fishing pier, 9-hole Seaside Sports putting course, beach volleyball, waterfront bocce ball, complimentary kayaks and paddleboards, bike rentals, Islander Watersports on-site, gift shop, fitness center, and massages on request.
Dining: You Don’t Need to Leave
- Tides Beachside Bar & Grill – Casual, upbeat, right on the beach. The Jumbo Lump Crab Rarebit and Mango Shrimp Tacos are legendary.
- Drift on the Beach – More upscale seafood, perfect for sunset. Spicy Palomas and macadamia-crusted seared tuna.
Service That Feels Like Family
From reception to grounds crew to restaurant staff, everyone exudes hospitality. Free parking and free Wi-Fi throughout.
From sunrise coffees to sunset cheers, The Islander gave us memories we’ll never forget. Lovely, clean, gorgeous grounds & super quiet.
The Islander Resort – 82100 Overseas Hwy, Islamorada, FL 33036 – MM 82.1 Oceanside
Link: https://www.islanderfloridakeys.com/
More Islamorada / Upper Keys Favorites
Italian Food Company, Islamorada
If you want Italian that feels like it belongs in the Keys, this is it. The wood-fired Margherita pizza and house-made tiramisu pull rave reviews, and the cacio e pepe made right in the cheese wheel in front of you is a showstopper.
The vibe is fun and easy-going, with live music and karaoke adding energy. People keep coming back for the pizza, pasta, and sangria in the cozy outdoor area.
Link: https://italianfoodcompany.com/
Pinfish Entertainment, Tavernier
Rainy day? Too hot? Pinfish is the Upper Keys’ go-to indoor escape. It mixes duckpin bowling, axe throwing, and a prize-packed arcade with craft beer and wine from a self-serve tap wall.
Families love it because kids can bowl and play arcade games while adults enjoy axe throwing and food. Locals use it for date nights and leagues, and visitors say it’s a must-stop for families driving through the Keys. Clean, well-maintained, and lively without feeling chaotic.
Link: https://www.pinfishentertainment.com/
Ocean Drive Indoor Golf, Islamorada
This is Islamorada’s year-round indoor golf lounge, open to the public for family outings, date nights, group events, or solo practice. With a 4.7 rating, reviewers call it “very fun” and praise the owner for being super cool and welcoming. It’s the #1 Fun & Games spot in Islamorada on Tripadvisor, perfect when you want to swing without dealing with heat or rain.
Link: https://golfoceandrive.com/
Keyz Charters to Alligator Reef Snorkeling
They run eco-friendly, private snorkeling tours to Alligator Reef where you’ll see parrot fish, nurse sharks, barracudas, and more.
If you only do one thing in Islamorada, make it a private charter with Keyz Charters. This is not the 40-person cattle boat where you are rushed in and out of the water. This is the Keys the way locals do it.
Their base philosophy: eco-friendly, education + adventure. You don’t just see the reef, you understand it.
1. Alligator Reef Snorkeling – Their Signature
This is what they are famous for. Alligator Lighthouse is about 4 miles offshore and sits on one of the best-preserved sections of the only living coral barrier reef in North America.
We did the 2-hour snorkel. Captain Kristi took us out when conditions were perfect – minimal current, seas flat. You anchor in 5-15 feet of crystal clear water right at the lighthouse. In one snorkel we saw: parrot fish, angelfish, yellowtail snapper, barracuda, nurse sharks, brain coral, fan coral, and a sea turtle. It truly feels like swimming in an aquarium.
What makes KeyZ different: They provide everything you need, they are incredibly knowledgeable about the reef and local ecosystem, and they will time your trip for the best visibility and least current. They also tailor it for all ages and for dogs – super dog-friendly and patient with timid swimmers.
Other Services – Way More Than Just Snorkeling
This is why you can book them 2-3 times in one trip and have a totally different experience each time:
A) Eco-Tours (2-hour and 4-hour)
Discover the natural wonders of the Florida Keys through crystal-clear waters, lush mangroves, and diverse wildlife habitats. This is a slow cruise through Florida Bay and Everglades National Park boundaries. You will cruise through mangrove tunnels, channels & open sea. Spot tons of birds, a crocodile, lizards, search for the elusive manatees, dolphins, sharks, and learn about the ecosystem from a real marine biologist. From the “bird sh*t sticks” to sharks, they know every story. Perfect for families with little kids who can’t snorkel long.
B) Sunset Cruises / Sunset Eco-Cruise (2 Hours)
Locals know to call KeyZ for sunset. This is the perfect way to unwind. Calm waters, soothing waves, ocean breeze, and that famous Keys sunset where the sky explodes pink and orange as the sun dips below the horizon. They combine it with a mangrove tour so you get wildlife + sunset in one. Romantic, relaxing, and you can BYOB or do their bar-hopping version.
C) Historic Island Tours
A unique way to experience the rich history and natural beauty. They take you to:
- Lignumvitae Key – home to Florida’s oldest botanical gardens, with a virgin tropical hardwood hammock and diverse native plants & wildlife you can’t see anywhere else.
D) Islamorada Sandbar Tours
Their “chill day” tour. They take you to pristine sandbars just off Islamorada, Key Largo, and Marathon. You anchor in knee-deep, crystal-clear water. Swim, snorkel among vibrant marine life, or just relax and soak up the sun on these sandy oases. The ultimate escape and the most Instagrammable spot in the Keys.
E) Custom Combination Tours
This is the secret weapon. Along with their most popular tours, they will create your own unique boat tour. Want to do snorkeling + sandbar + sunset? Done. Want to go bar hopping by boat? Propose to your significant other on a private sunset cruise? Bird-watching charter focused on roseate spoonbills? They build it for you.
Happy Travels 