Let's be real, there's something incredibly liberating about ditching your swim trunks and feeling the Florida sun on, well, everywhere. Key West has long been a haven for gay men seeking that perfect blend of tropical paradise, vibrant nightlife, and the freedom to be completely yourself. And when we say "completely yourself," we mean exactly that: no tan lines, no judgment, just pure, unapologetic freedom.
If you've been dreaming of a getaway where clothing is optional and the vibes are immaculate, Key West delivers in spades. This tiny island at the southernmost tip of the continental U.S. has carved out a reputation as one of the most LGBTQ+-friendly destinations in the world, with several incredible clothing-optional resorts designed specifically for gay men. Whether you're looking to unwind poolside with a cocktail, meet fellow travelers, or simply soak up the sun au naturel, Key West has your back (and front, and… you get it).
Why Key West?
Before we dive into the specific resorts, let's talk about why Key West is the spot for a clothing-optional escape. This island has been a queer sanctuary for decades, with a thriving gay scene that's woven into the very fabric of the community. Rainbow flags fly proudly on Duval Street, the bars are welcoming and wild, and nobody bats an eye at two men holding hands, or, in the case of these resorts, holding nothing but a tropical drink.
The weather is spectacular year-round, the sunsets are legendary (Mallory Square, anyone?), and the laid-back island vibe makes it easy to leave your worries, and your clothes, at the door. Plus, with several men-only and clothing-optional properties concentrated in a relatively small area, you've got options that cater to different styles and budgets.
Island House: The Crown Jewel
If there's one resort that consistently tops the list for gay men's clothing-optional stays, it's Island House. This place is legendary, and for good reason. As the largest men-only clothing-optional resort in Key West (and proudly the oldest gay-owned and operated men's resort in the world), Island House has perfected the art of creating a space where you can completely let loose.
Located about a 15-minute walk from the main Duval Street action, Island House offers a little distance from the tourist hustle while keeping you close enough to pop out for dinner or drinks. The property itself is stunning: lush tropical landscaping, a gorgeous pool area, and a sprawling clothing-optional sundeck where you can work on that all-over tan.
What really sets Island House apart are the legendary pool parties. Every Wednesday from 5-8 pm and Sunday from 12-4 pm, the resort transforms into the hottest party spot on the island. The energy is electric, the music is pumping, and the crowd is diverse and welcoming. Even if you're not staying at the resort, you can snag a day pass for $50, which includes locker access and full use of all amenities. Trust us, it's worth every penny.
The accommodations range from cozy rooms to luxury suites, all designed with comfort and style in mind. And the best part? You can walk from your room to the pool to the bar without ever worrying about dress codes. It's clothing-optional heaven.
Alexander's Guest House: Upscale Intimacy
If you're looking for something a bit more refined and intimate, Alexander's Guest House delivers an upscale experience in the heart of Old Town. This property is unique in that it welcomes both men and women, creating a more relaxed, less "cruisy" atmosphere while remaining proudly gay-owned and operated.
Alexander's features at least two clothing-optional sun decks, giving guests plenty of space to lounge in the buff without feeling crowded. The rooms are spacious and well-appointed, with king-sized beds, private balconies, and tasteful decor that feels more boutique hotel than party resort.
What really elevates Alexander's is the attention to detail and hospitality. Guests enjoy complimentary breakfast each morning, daily evening cocktails, and access to communal sunning decks, a pool, and a hot tub. There's also an in-house bar where you can grab a drink without leaving the property. The vibe here is sophisticated and welcoming, perfect for couples looking for a romantic getaway or solo travelers who want to relax without the party scene.
New Orleans House: Downtown & Convenient
Location, location, location, that's what New Orleans House has going for it in spades. As the only male-only clothing-optional resort located directly on Duval Street, you're literally in the center of everything. Step out the front door and you're surrounded by bars, restaurants, shops, and the iconic gay nightlife that Key West is famous for.
The resort itself centers around a lush, tropical courtyard that's accessible through the adjacent Bourbon Street Pub. The clothing-optional pool area and sundeck provide a private oasis where you can strip down and relax, all while being just steps from the action.
New Orleans House keeps things simple but comfortable, with free breakfast to start your day, happy hour to kick off your evening, gym access for those who actually want to work out on vacation, and complimentary entry to Bourbon Street parties. If you're the type who likes to be in the thick of things, able to bounce between the resort pool and the bars on Duval without missing a beat, this is your spot.
Garden of Eden: A Different Kind of Freedom
Okay, so Garden of Eden isn't technically a resort, it's a clothing-optional rooftop bar perched atop the Bull and Whistle Bar on Duval Street, but it deserves a mention because it's an absolute must-visit experience. This is Key West's only clothing-optional rooftop space, and it welcomes both men and women.
Picture this: panoramic views of the island, ocean breezes, themed events, and the freedom to dance, drink, and socialize completely nude if you choose. It's a wild, liberating experience that perfectly captures the anything-goes spirit of Key West. Even if you're staying at one of the resorts, make sure to add a night at Garden of Eden to your itinerary. It's unforgettable.
Practical Tips for Your Clothing-Optional Escape
Respect the Spaces: Clothing-optional doesn't mean clothing-mandatory, or nudity-mandatory, for that matter. These resorts welcome guests to be as covered or uncovered as they're comfortable with. Just be respectful of the property rules and other guests.
Sun Protection is Crucial: Yes, we're talking about everywhere. Don't forget to apply sunscreen to areas that don't usually see the light of day. Trust us, a sunburn in certain spots is not a souvenir you want to take home.
Day Passes: If you're staying elsewhere or just want to explore multiple properties, many of these resorts offer day passes. It's a great way to sample the vibe before committing to a multi-night stay.
Book Early: These resorts, especially Island House, can fill up quickly during peak season (winter months and special events like Fantasy Fest). Reserve your spot well in advance.
Note on Closures: Equator Resort, which was previously a popular clothing-optional option, closed permanently in January 2024. Make sure you're booking at currently operating properties.
Beyond the Resorts
While the clothing-optional resorts are incredible, don't forget to explore everything else Key West has to offer. The gay bar scene on Duval Street is legendary, with spots like 801 Bourbon and Aqua drawing crowds every night. The food scene is fantastic, the drag shows are top-notch, and the sunset celebrations at Mallory Square are a must-see.
And if you're a reader (which, let's be honest, you probably are if you're here), consider bringing along some MM romance novels from Read with Pride to enjoy while lounging poolside. There's something perfectly decadent about reading a steamy gay romance while soaking up the sun at a clothing-optional resort.
Final Thoughts
Key West's clothing-optional resorts offer more than just a place to shed your swimsuit: they provide a genuine sense of freedom, community, and acceptance that's increasingly rare in today's world. Whether you choose the legendary parties at Island House, the upscale intimacy of Alexander's, or the downtown convenience of New Orleans House, you're guaranteed an unforgettable experience.
So pack light (you won't need much), slather on that sunscreen, and get ready to experience Key West the way it was meant to be experienced: with complete freedom to be your authentic self.
Ready to explore more LGBTQ+ travel destinations and the best in gay romance? Follow us on Facebook, Instagram, and Twitter, and discover incredible MM romance books and queer fiction at Readwithpride.com.
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