You know that feeling when you cross the Matanzas Pass Bridge and the salt air hits your face? That’s the moment. For anyone headed toward Diamond Beach Resort Fort Myers Beach, that bridge is the gateway to a very specific kind of Florida lifestyle. It’s not the glitz of South Beach. It’s not the manicured perfection of Naples. Honestly, it’s better. It’s a bit raw, incredibly sun-drenched, and currently, it’s a symbol of a community that refuses to stay down.
Fort Myers Beach has been through the wringer. If you’ve followed the news at all since late 2022, you know the island took a direct hit from Hurricane Ian. It changed everything. For a while, people weren’t sure what would happen to the iconic spots along Estero Boulevard. But the Diamond Head Beach Resort—often referred to by locals simply as Diamond Head—didn't just survive; it became a cornerstone of the recovery. It’s one of those places where the regulars have been coming for thirty years, and now they’re bringing their grandkids to see the same Gulf sunsets, albeit with a slightly different skyline in the background.
The Reality of Staying at Diamond Head Beach Resort Right Now
Let's get real for a second. If you book a room here expecting a silent, untouched paradise, you haven't been paying attention to the geography. The island is rebuilding. You're going to see cranes. You’re going to hear the occasional hum of construction. But here’s the kicker: the resort itself is a sanctuary. While much of the surrounding area is in various stages of "coming back," Diamond Head has managed to maintain its full-service feel.
The suites are huge. We’re talking 700 square feet of space, which is basically a small apartment. You’ve got a separate bedroom, a living area, and a kitchenette. This is huge for families. Nobody wants to be tripped over by a toddler while trying to make coffee at 7:00 AM. Having that screened-in lanai makes all the difference. You can sit out there, watch the dolphins play in the distance, and feel like the world is exactly as it should be.
Why the Location Actually Matters
Location is a buzzword people throw around, but here, it’s literal. You are steps from the sand. Not a "short walk." Not "across the street." You are on the beach. To the north, you’ve got the Times Square area, which used to be the heart of the island's nightlife and shopping. It’s still finding its feet, but the energy is returning. To the south, the island stretches out toward Lovers Key State Park.
💡 You might also like: The Largest Spider in the World: What Most People Get Wrong
Being centrally located means you can walk to several of the reopened local haunts. Cabanas Beach Bar & Grill, located right on the property, is basically the social hub of this stretch of sand. You can grab a fish taco, a cold beer, and just watch the tide. It’s low-key. It’s unpretentious. It’s exactly what Florida should be.
What Most People Get Wrong About the Post-Storm Experience
There’s this misconception that Fort Myers Beach is "closed." That’s just wrong. In fact, visiting now is probably more impactful than it was five years ago. Your tourist dollars are literally fueling the local economy's heartbeat. When you stay at a place like Diamond Beach Resort Fort Myers Beach, you aren't just a guest; you're a patron of the island's future.
The beach itself is as beautiful as ever. The sand is that powdery white quartz that stays cool under your feet even when the sun is blasting. The water is shallow and warm. Sure, some of the old landmarks are gone, replaced by empty lots or new developments, but the essence of the place—the "vibe"—hasn't shifted. It’s still the place where you wear flip-flops to dinner and nobody cares if your hair is messy from the wind.
Amenities and That Famous Pool Deck
The pool at Diamond Head is legendary. It’s elevated, so you get these sweeping views of the Gulf while you’re lounging. They have these poolside cabanas that are worth every penny if you’re planning to spend the whole day out there.
📖 Related: Sumela Monastery: Why Most People Get the History Wrong
- Chloës Seafood & Steaks: This is the upscale option on-site. It’s surprisingly refined for a beach resort.
- The Fitness Center: It’s functional, but honestly, why are you on a treadmill when you can run miles of coastline?
- Beach Service: They set up the chairs and umbrellas for you. Don't fight with a rusty beach chair you bought at a drugstore. Just let them handle it.
The service here feels different than at the big corporate chains. Most of the staff have been there for years. They know the island. They can tell you exactly which sandbar is the best for shelling after a morning tide or which local captain is currently running the best sunset cruises. That kind of institutional knowledge is rare these days.
Navigating the Logistics of Your Trip
If you’re flying in, you’re looking at Southwest Florida International Airport (RSW). It’s an easy 30-to-40-minute drive depending on traffic. Don’t bother with a rental car if you don’t plan on leaving the island much. Use a rideshare or a shuttle. Once you’re at the resort, you can use the Freebee—a local electric shuttle service—to get around the island. It’s convenient, eco-friendly, and free. You just download the app and request a ride.
Parking on the island can be a nightmare, but guests at Diamond Head have it easy with on-site parking. Just keep in mind that traffic on Estero Boulevard can move at a snail’s pace during "Season" (January through April). Plan accordingly. If you have a 6:00 PM dinner reservation, leave at 5:30 PM even if it’s only a mile away. Relax. You’re on island time.
The Sustainability Factor
There's been a massive push lately to protect the local ecosystem, specifically the sea turtles. Between May and October, "Long Live the Turtles" isn't just a slogan; it’s a rule. You have to turn off your balcony lights and close your curtains at night so the hatchlings don't get confused by the artificial light. It’s a small price to pay to ensure the wildlife keeps coming back. The resort is pretty strict about this, and for good reason.
👉 See also: Sheraton Grand Nashville Downtown: The Honest Truth About Staying Here
Final Thoughts on the Diamond Head Experience
People ask if it's "worth it" to go back yet. The answer is a resounding yes. You get the luxury of a full-service resort with the grit and heart of a community that’s rebuilding. It’s a unique moment in the history of Fort Myers Beach. You’ll see the scars of the past, but you’ll also see the incredible resilience of the people who call this place home.
Diamond Head remains the "Big House" on the beach. It’s sturdy, it’s welcoming, and it offers a level of comfort that’s hard to find elsewhere on the sand right now. Whether you're there for the world-class shelling, the margaritas at Cabanas, or just to stare at the horizon until your brain stops buzzing, it delivers.
Actionable Steps for Your Visit
- Book Directly: Often, the resort website has "Florida Resident" or "Last Minute" specials that don't show up on the big booking engines.
- Download the Freebee App: Do this before you arrive so you can hop around the island without worrying about parking your car.
- Check the Tide Charts: If you’re into shelling, the best treasures appear at low tide, especially after a storm or a period of high winds.
- Support Local Small Biz: Grab your morning coffee at a local stand or buy your souvenirs from the shops that have managed to reopen nearby.
- Pack Light: You really only need swimwear, a couple of casual outfits, and high-quality sunscreen. The resort has laundry facilities if you're staying for a week or more.
The island is waiting. The sand is white, the drinks are cold, and the sunsets at Diamond Beach Resort Fort Myers Beach are still the best show in town. Go see for yourself.