50 years of Island House: How this iconic Key West guesthouse is still thriving

When I posted my first shirtless thirst trap from Island House, I was met with an overwhelming response: “Move your camera down!”

Often punctuated with a devil or winking face emoji, friends and strangers alike shared their love for the historic Key West guesthouse–and the shirtlessness that thrives there. Established in 1976, Island House is celebrating its golden birthday this year with pool parties, heavy pours, and yes, nudity.

While that last part is the most eye-popping, don’t let the clothing-optional vibe intimidate you. The “live and let live” ethos that’s pervaded Key West for a century is prevalent inside the enchanted walls of Island House. It’s a place where gay men of all stripes feel free–from shameless selfie takers to laidback loungers.

General manager Jeffrey Smead enjoys watching guests transform from bashful to boastful. “It’s always by the end of day two that shy guests muster the courage to join their tribe and get naked,” he said.

For what it’s worth, it took this guest three.

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“Try kissing your husband at the Hyatt.”

Four miles long and one mile wide, Key West was once home to 20 gay guesthouses. The first resort opened in 1967 and is still operating today. But like some of the island’s hotels and businesses, it is less gay-centric than it once was.

The island’s economy was supercharged in the New Deal era with the Federal Art Project, which lured creatives to the southernmost point of the U.S. Locals, who call themselves Conchs or “Bubba,” like to joke that Key West is the end of the road. As one bartender told me, no one winds up in Key West by accident.

As with many artistic havens, such as Provincetown and Fire Island, the gays were among the first to populate Key West’s rocky shores, turning it into an oasis where everyone could be themselves. By the ‘90s, Key West was firmly established as a mecca.

As Jeffrey’s husband, James Braun, told me, “Go to the Hyatt and try kissing your husband in the mouth in the hot tub.”

At Island House, boys are free to be boys. That’s just as valuable in 2026 as it was in 1976, which is why Island House’s 39 rooms are almost always sold out, along with their new luxury villas, which guests rent for a month at a time. Renovated and sleek, the rooms offer cozy bedding, flat-screen TVs, and ample closets and lounge areas — including a sofa and a plush recliner (as well as a bidet). With those high-end amenities, many of the resort’s regulars visit multiple times per year.

It’s easy to see why.

There’s non-stop action, from the raucous happy hour pool party (four complimentary drinks per guest) to late-night romping in the resort’s “Red Room.” But for the more introverted, there’s plenty of quiet time by the pool to simply catch up on your favorite novel and soak in the ever-present sunshine while sipping a beverage. One of my favorite daily rituals was grabbing a chair on the roof deck, enjoying the late-afternoon sun in peace.

Catering to the crowd

Nick Vannello has been coming to Island House since the late ‘80s. As the founder of a nudist-friendly travel group, GoNaked Travels, he understands the sanctity of male bonding.

Island House is the perfect forum for the group’s members to get loose. Many of them were still coming out in the earlier stages of their lives, and today want to live as freely as possible.

That’s the kind of frolicking atmosphere that Smead and Braun curate. They are themselves a product of the property’s magic: They met at the resort’s 24-hour cafe, at table 3.

Island House isn’t just a resort for gay men. It’s also a resort by gay men. Smead and Braun know what their clientele wants, but they’re looking for the same adventures themselves.

“This is the most fun I’ve had in my entire life,” said Braun.

It’s a sentiment that many of the resort’s guests share. One of them, Chase Bourgeois from Louisiana, fondly recounts the time he was invited to appear in another guest’s OnlyFans. He says he and his husband were so “taken by their experience” that they returned four more times in the same year.

John Dorn, another frequent guest, says that when he sends friends to Island House, they often check back in and let him know they haven’t left the property.

“Is that normal?” they ask.

It’s a question I asked myself, as I sipped a key lime martini poolside in the wee hours of the morning, chatting up a pair of visitors whom I had met at Island House’s weekly Wednesday pool party (5:00-8:00 p.m.).

The answer is, absolutely not. Island House serves poolside drinks until 4:00 a.m., then resumes service at 7:00 a.m. Food from the full kitchen at the pool bar is available 24 hours. Taste fare ranges from poolside snacks such as sandwiches and salads to ribeye steaks and grouper dinners.

For those who do want to venture outside of the property, Island House is located in the heart of Key West’s historic Old Town, filled with breathtaking, pastel-colored homes that exude Southern stateliness. The entire island is walkable, and though meals on Duval Street can be pricey, there are plenty of more budget-friendly options.

Sandy’s Cafe, located less than half a mile from Island House, has the best Cuban sandwich on the island. Date & Thyme, an organic cafe and market, is just a short stroll away and offers fresh juices, smoothies, avocado toast, wraps, salads, and more.

On my first afternoon, I strolled down Duval and enjoyed an iced latte from Moondog Cafe, which has a full dinner menu, delectable pastries, and a prime location: it is a stone’s throw away from the historic Ernest Hemingway Home and Museum.

At night, the gay bars along Duval are overflowing with locals and tourists alike, with drag offered at Aqua Nightclub and revelry at mainstays Bourbon Street Pub, 801 Bourbon Bar, and La Te Da.

Locals gather late-night at Bobby’s Monkey Bar, where there’s always pool, karaoke, and camaraderie. When I walked in, I was greeted by a lovely woman named Karen, who served me at a wine bar on Duval (Vinos on Duval) the previous night. She welcomed me with a hug.

Being all-in

Smead and Braun are committed to ensuring that Island House thrives for another half century. The resort’s owner, Bobi Lore, became the sole proprietor when his husband passed away in 2020. Smead and Braun have been running day-to-day operations since 2021. They live around the corner from the property and always set aside rooms for members of their staff, since the cost of living in Key West can be high.

They take care of their employees, who, in turn, dedicate themselves to delivering excellent service. Multiple bartenders and pool boys told me it’s the best job they’ve ever had.

Smead and Braun love watching guests relax and liberate themselves from the anxieties of everyday life. “As soon as that freedom hits, they’re a renewed man,” said Smead.

That was certainly my experience. Back home in Chicago, I already miss Island House.

By the way, if anybody finds my missing sandals, tank top, and sunglasses, let me know. I told you: by day three, everything came off.

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