When my partner and I first landed in Key West, we had no idea it would become such a defining part of our lives. Our first visit was for Fantasy Fest—what we thought would be a one-off trip quickly turned into a yearly tradition. Fast-forward 20 years: we bought a house, became part-time locals, and found ourselves fully immersed in the Island House community.
Island House Key West Resort isn’t just a place to stay—it’s a vibe. This iconic, clothing-optional gay resort blends tropical charm with a strong sense of community. Tucked away like a drag queen’s package, right in the heart of Old Town Key West, it serves up food, drinks, naked men, and Florida sunshine—basically, a queer man’s playground. From the outside, you’d never guess that behind that low-key entrance on Stickney Lane, a bunch of guys are confidently letting it all hang out—literally! But step inside, and boom—you’ll know you’re in for something special—equal parts paradise and party, with a side of “I never want to leave.”
From a 24-hour pool to a cruisy sauna and gym, Island House invites you to relax, connect, and just be. Whether you’re here for flirtation, friendship, or a quiet moment by the pool, there’s room for it all. It’s not just a resort—it’s a sanctuary of freedom, joy, and that gay Key West magic.
Curious about what makes Island House so unforgettable? Let’s unpack the experience—from first impressions to packing tips and play-it-cool etiquette.
The Vibe: Clothing-Optional, Sex-Positive, and Surprisingly Sweet
Picture a tropical escape under a canopy of swaying palms with a sparkling pool and a hot tub that’s bubbling with warm water and just the right amount of naughty energy. Island House Key West sets the scene with enticing amenities like poolside cocktail service, an in-house licensed massage therapist, and expertly curated playlists (yes, it matters). And with rooms that blend comfort and intention—with memory foam beds for late-night recovery, mood lighting for whatever the moment calls for, and yes, even bidets.
What does “clothing-optional” really mean? Exactly what you think. You can be fully dressed, lounging in swim trunks, or confidently rocking your birthday suit. No judgment, no pressure.
What about “sex-positive”? That’s Island House’s way of saying this is a safe space to explore. While there’s no expectation to engage (or witness) anything scandalous, you’ll find the atmosphere is unapologetically open. Whether you’re here for a romp in the Red Room—also known as the Library (or The Cultural Arts Center)—or to sip a frozen Tara Reid (mango-strawberry purée, peach vodka, coconut and mango rum—pure vacation in a glass—that’s been their top seller for two decades), the choice is completely yours.
Expression is everything here—whether it’s bold speedos, skipping clothes altogether, tattoos, piercings, or just killer sunglasses. This is where individuality shines—like the disco ball hanging over the pool. Whether you’re mingling or recharging solo, Island House lets you do you. You get to curate your stay to match your vibe, your comfort level, and your mood.
Flirty but Friendly: That’s probably the best way to describe it. The energy is laid-back and welcoming—even surprisingly sweet. It’s not about being “on” all the time; it’s about the freedom to just be.
Confidence, Curiosity, and the (Gay) Gaze
The first time I walked into Island House, I immediately thought: “I should’ve gone to the gym.” Seriously, walking into a clothing-optional, OnlyFans-worthy pool scene can stir up all sorts of feelings—from nervousness to your inner diva screaming, “You’ve got this, hun!”
But here’s the twist: Island House celebrates all bodies. Yes, there are Adonises with tan-line-free confidence. But there are also silver foxes, dad bods, twinks, bears, shy guys, and bookworms deep in their Real Housewives memoirs. Nobody’s judging you except… you. And guess what? You don’t need to.
One moment, you’re feeling self-conscious. The next, you’re watching an older couple laugh over cocktails while two guys—who clearly just met—make out nearby like it’s their honeymoon. And somehow, it all feels perfectly normal.
That’s the magic: Island House isn’t about “hot guys only”—or “No Fats, No Fems,” to use Grindr parlance. It’s about authenticity. By my second visit, I stopped worrying and just leaned in. And now? A hot tub hang with strangers can easily lead to dinner at the Island House café—where, yes, you can still be naked, and yes, the food is ridiculously good.
From Flirtation to Friendship
Island House is a social butterfly’s dream. Yes, it’s precisely the kind of place where you can flirt your way through Happy Hour (daily from 5 pm to 6:30 pm). But, even as an introvert, I felt instantly at ease. The laid-back, no-pressure vibe makes it easy to just be yourself. And what might surprise you is how often those casual moments turn into real, lasting connections.
Here’s where it gets good:
- Casual Chats: Hanging by the bar, chatting up an ungodly hot bartender about local Key West events, or—like me—starting off too shy to say a word, then finding yourself in the pool full of friendly strangers. Just introduce yourself, ask where they’re from, and throw in a classic, “So, what Lady Gaga song are you?” Before you know it, you’re bonding over shared stories, laughing like old friends, and wondering why socializing doesn’t always feel this effortless.
- Recurring Characters: The beauty of Island House is that you’ll often meet local members or guests who return year after year. Soon enough, you might find yourself on an annual brunch hang with people who used to be strangers.
- Pool Parties: Sundays (12 pm-5 pm) and Wednesdays (5 pm-8 pm) are sacred, and trust me, they’re legendary. The friendly pool boys keep things lively with free shots, while raffles and giveaways add an extra layer of excitement.
- Key West Nightlife: Whether you’re catching an unfiltered drag show at 801 Bourbon or soaking up the anything-goes vibes at Saloon One, this town knows how to party—and odds are, you’ll be out there with your new Island House friends, living your best life long after the sun goes down.
Why You Should Get Naked
Let’s be real: there’s something freeing about stripping down—physically and emotionally. Island House makes it easy. No tight waistbands, no decision fatigue over which tank top says, “I’m fun but chill.” You just show up as you are, and somehow, that’s more than enough.
Your balls will thank you. Seriously. That breeze-on-your-bits feeling? Life-changing. Once you’ve floated in the pool in your full glory, undies start to feel like a scam.
Nudity leads to connection—whether you’re solo or with a partner. Being this open strips away the layers (pun intended) and can bring you closer, to others and yourself. Many couples say they leave Island House feeling more bonded—and way more turned on.
The best part? You’ll leave proud. Because you did the thing. You let it all hang out—and loved every second of it.
Packing for Island House (Yes, You Need Sunscreen Everywhere)
Wondering what to pack for a clothing-optional, sex-positive resort? Keep it light, comfy, and just a little cheeky:
- Sarongs & Sheer Things – Great for lounging or walking around like a sexy Jedi. But if you’re heading off-property, pack something light and breezy—Key West weather doesn’t exactly demand layers.
- Slip-On Sandals – Easy on, easy off—like everything else here.
- Confidence Essentials – Sunscreen (yes, for all your parts), a hat, sunglasses, and your boldest swimwear. Just in case you decide to hit the beach.
- Playthings – You know what we mean. But don’t stress—Island House discreetly stocks the essentials if you forget.
- Something Cute – You’ll want a casual-cute outfit for nighttime adventures in town.
That’s it. Pack light, show skin, and let your confidence do the heavy lifting.
Etiquette Tips for Staying at Island House
Staying at Island House—or any gay clothing optional resort—isn’t just a getaway; it’s an experience. And like any fabulous party, knowing the vibe and the etiquette can make all the difference. So, let’s break it down:
- Boundaries Are Sexy. Not everyone is a hugger—or a nudity enthusiast. Consent is everything, whether it’s for a handshake or… anything else. And think twice before you snap. Always, always ask before taking a picture. Respect the “no paparazzi” rule—this isn’t the Met Gala.
- Read the Room, Honey. Be friendly, sure, but take a moment to feel the energy. Some folks are there to zen out; others might be down for a cocktail-fueled chat. Know your audience.
- Bodies Are Beautiful (Yes, Yours Too). Seriously, leave your insecurities at the door. These spaces are all about inclusivity. Whether you’re rocking a dad bod, gym bod, or “I love carbs” bod, you’re golden here.
- Rules Keep the Party Going. Listen, rules aren’t just there to kill the vibe—they’re there to preserve it. Whether it’s clothing-optional zones or non-smoking areas, stick to the script so everyone can keep basking in the good vibes.
Looking for More?
Ready to take the plunge (literally or metaphorically)? Start planning your trip to Island House Key West. For insider tips or a deeper dive into all things gay Key West, check out our city guide.
Still undecided? Trust us—lean into the experience, and you might just walk away with more than a tan. And even if you’re not staying at Island House, grab a day pass for $50 to see what the hype is all about.
Photos by Nick Doll, Tristan Sutphin and Larry Blackburn for the Island House Key West
Note: This article was sponsored by the Island House Key West. All opinions are our own—we never compromise integrity for sponsorship.