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This is where you’ll spot rainbow crosswalks and can easily visit the most popular gay bars and nightlife.

Parties and events – Some gay resorts in Key West host events or other parties and social gatherings at their properties. As LGBTQ+ people became more visible and acceptance grew, several companies began creating trips specifically for the LGBTQ+ community.

You’ll leave proud. Island House has won a variety of awards from BOYZ and Out Traveler magazines, as well as top recognition from TripAdvisor.

Alexander’s Guest House – Island Oasis Boasting Tropical Elegance

Located on a quiet neighborhood street in the heart of Key West’s Old Town, this beautifully restored Key West Conch house, built in 1902, is proudly gay-owned and operated.

This iconic, clothing-optional gay resort blends tropical charm with a strong sense of community. Trust us—lean into the experience, and you might just walk away with more than a tan. All opinions are our own—we never compromise integrity for sponsorship.

Alexander’s Guesthouse – Key West’s Premier Resort

Welcome!

So, let’s break it down:

Looking for More?

Ready to take the plunge (literally or metaphorically)? Sign up with misterb&b  and you will receive a free $10 credit to use on your first booking!

There are many other sites for apartment rentals including Airbnb, Vrbo and Booking.com. 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.

When it’s time to head out for dinner and a night on the town, you’re just minutes from Duval Street and all the action.

New Orleans House – No-frills Guest House on Duval Street

This is the only gay, all-male guesthouse on Duval Street. Being this open strips away the layers (pun intended) and can bring you closer, to others and yourself.

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. The elegant yet modern and comfortable suites and guest rooms feel like a home away from home, featuring private baths, air conditioning, flat-screen TVs, mini-fridges, and modern amenities.

While there’s no expectation to engage (or witness) anything scandalous, you’ll find the atmosphere is unapologetically open. You literally couldn’t be any closer to the Old Town party scene.

gay resort florida keys

Aside from a few other destinations in the U.S., such as Palm Springs, Provincetown, and Fort Lauderdale, Key West is one of the top cities with the most gay and clothing-optional resorts in the country.

With its tropical climate, you can expect year-round warm weather, making it an ideal destination for sun, sea, sand, and sex at any time of year.

We welcome you like long time friends.

Alexander’s Guesthouse is a lovingly restored Key West Conch house built in 1902, boasting beautiful, original pine floors and stately windows. Whether you’re here for flirtation, friendship, or a quiet moment by the pool, there’s room for it all. Whether you’re mingling or recharging solo, Island House lets you do you.

Join the flocks of gays for annual celebrations and events like New Year’s Eve, Key West Pride in June, Tropical Heat in August, and Women Fest over Labor Day weekend.

No matter when you visit, you’ll want to stay close to the action, and there are plenty of hotels, resorts, and cute beach houses to choose from. Two on-site restaurants, Red Shoe Island Bistro and Pizza Joe’s, offer an array of tasty Key West eats and drinks.

misterb&b – A Home Away From Home

If you’re looking to live like a gay local when you visit Key West, check out the hundreds of accommodations available on Misterb&b.

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.

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.