Gay Key West: Best Gay Hotels, Bars & Nightlife on Bone Island (2026)
Key West is one of those rare places where you can spend the day in flip-flops and the night in a cabaret seat with a martini — and somehow it all feels perfectly normal. It’s quirky, historic, a little naughty, and proudly LGBTQ+… with everything from iconic gay bars on Duval Street to clothing-optional resorts where “tan lines” are optional too.
Whether you’re planning a long weekend, a Pride trip, or a full-on gay guesthouse getaway, this guide covers where to stay, what to do, where to eat, and how to party in Key West.
Whether you’re planning a long weekend, a Pride trip, or a full-on gay guesthouse getaway, this guide covers where to stay, what to do, where to eat, and how to party in Key West.
Why Visit Gay Key West?
Key West has been welcoming the LGBTQ+ community for decades — and you can feel it the moment you arrive. The vibe is come-as-you-are, the streets are packed with history, and the nightlife is ridiculously easy to navigate because it’s all centered around Old Town + Duval Street.
It’s also one of our favorite places for a U.S. gay getaway because you can do it your way: poolside and peaceful, bar-hopping and wild, or a little bit of both.
And if you’re turning this into a bigger Florida gay road trip, Key West pairs perfectly with Miami and Fort Lauderdale — our full guides linked in the post so you can map out the whole route.
KEY WEST TRAVEL ESSENTIALS
Planning your trip to Key West? These travel tools and services will save you money and make your visit stress-free:
🌟 Pro tip – Some links on this post are affiliate links, which means we may earn a small commission if you book through them—at no extra cost to you. Thanks for supporting our travels and helping us create more content like this!
Planning your trip to Key West? These travel tools and services will save you money and make your visit stress-free:
- Travel Insurance – Don’t leave home without it! SafetyWing offers super affordable travel insurance with straightforward pricing and flexible extensions—even if your trip is already underway. Protect yourself from unexpected medical expenses and travel mishaps while you explore Key West and beyond.
- Hotel Discounts – Score unbeatable deals with Booking.com, our preferred website to book hotels when traveling in the U.S. Create a free account to instantly unlock savings of 10% or more on over 100,000 hotels worldwide. You’ll also find member perks like free breakfast, early check-in, or even surprise room upgrades—perfect for elevating your stay.
- Tours & Experiences – Book unforgettable adventures in Key West with Viator. Whether you're exploring the mangroves on a kayak or enjoying a sunset boat cruise with wine, Viator makes exploring the island easy and fun.
🌟 Pro tip – Some links on this post are affiliate links, which means we may earn a small commission if you book through them—at no extra cost to you. Thanks for supporting our travels and helping us create more content like this!
Where to Stay
If you want to be close to the action, Old Town is the move. You’ll be near Duval Street, gay bars, restaurants, historic sights, and the best “walkable wander” energy in the Keys.
Here are our top stays — from iconic gay resorts to gay-friendly alternatives when the popular spots sell out.
Island House – The Legendary Men-Only, Clothing-Optional Resort
⭐ Best for: All-in gay resort experience + pool parties + meeting guys fast
📍 Location: Old Town (Fleming Street / “gay guesthouse row” area)
Why We Love It:
- Men-only, clothing-optional vibes (aka: freedom)
- Iconic pool scene + social atmosphere
- Spa / steam / sauna energy when you want to turn things up
- Easy to grab a day pass even if you’re not staying onsite
Island House is a Key West institution — the kind of place where you “pop in for lunch” and suddenly it’s midnight and you’ve made ten new friends. If you want a trip that feels unapologetically gay from the second you check in, this is it.
🌟 Pro tip – We share behind-the-scenes, the real tea, and the spicier details (including Bone Island Bare It All, which happens twice a year) over on our Patreon.
Alexander’s Guesthouse – Gay-Owned Classic with Easy Social Vibes
⭐ Best for: Friendly guesthouse energy + relaxed Key West charm
📍 Location: Old Town (near Island House)
Why We Love It:
- Gay-owned and super welcoming
- Great for travelers who want social, but not “all-out resort”
- Prime location for walking to nightlife
Alexander’s is one of those places that nails the Key West guesthouse vibe — warm, easy, and community-forward. It’s a great choice if you want an upscale gay stay with a little more calm than a full resort scene.
New Orleans House – Iconic Gay Hotel + Bourbon St. Pub Pool Scene
⭐ Best for: Duval Street nightlife + day drinking done right
📍 Location: Duval Street (in the heart of gay nightlife)
Why We Love It:
- Bourbon St. Pub energy downstairs
- Easy access to 801 Bourbon Bar + other gay hotspots
- Pool + party atmosphere without needing to go far
If your ideal Key West trip includes “just one drink” that turns into an all-day situation — New Orleans House is the perfect base.
La Te Da – Gay-Friendly Boutique Stay + Cabaret Icon
⭐ Best for: Couples, cabaret lovers, and glamorous Duval Street energy
📍 Location: Upper Duval Street
Why We Love It:
- Adults-only and beautifully located
- A “night out” built into your hotel (hello, cabaret!)
- Great for date-night trips
La Te Da is one of those Key West experiences that feels like a tradition. You’re staying right where the magic happens — and it’s an easy yes if you love classic cabaret + strong cocktails.
The Porch on Frances Inn – Our Favorite Backup When Island House Sells Out
⭐ Best for: A gay-friendly alternative close to Island House (great value)
📍 Location: Old Town (right around the corner from Island House)
Why We Love It:
- Close enough to walk to Island House for a day pass or meals/events
- Great option when Island House is booked or pricing is wild
- Quiet, charming, and still very “in the mix”
The Porch on Frances Inn is our go-to “Plan B that doesn’t feel like Plan B.” You keep the location advantage, and you’re still steps from the gay guesthouse scene. Plus it's one of the highest rated guesthouses on the island!
Things to Do
Key West is small, walkable, and packed with personality — historic homes, ocean views, sunsets, and just enough chaos to keep it exciting. Here are our must-dos.
Hop on the Conch Train – Touristy? Yes, but perfect for first-timers to get the lay of the land and pick your “must return” spots.
Take the Southernmost Point photo – Yes, the line is annoying. Yes, you still have to do it.
Hemingway Home & Museum – One of the island’s most famous attractions — and the cats are basically celebrities.
Hit the Gay Beach at Fort Zachary Taylor State Park – While we’ll always be pool guys in Key West (those guesthouse pools are hard to beat), if you’re craving a proper beach day, this is hands-down the best beach on the island.
Sunset at Mallory Square – Street performers, snacks, live music, and the nightly ritual of everyone collectively losing their minds over the sky.
Sunset Sail (Must-Do) – This is peak Key West: golden-hour sailing, salty ocean breezes, and that end-of-day glow that makes everyone look hotter. If you want gay-only, book Sail Blu Q on select dates (BYOB and always a blast). Prefer gay-friendly with everything included? Book this sunset sail that comes with unlimited wine and beer plus hors d’oeuvres—the perfect way to toast the island before you hit Duval Street.
Where to Eat and Drink
Key West is all about easy island indulgence: seafood, Cuban coffee, conch fritters, and a “why not get dessert too?” attitude.
Pepe’s Café – Classic Key West Breakfast. Our longtime breakfast favorite in Key West. Expect hearty comfort food, friendly service, and a lively crowd of locals and visitors fueling up for the day. There’s usually a wait—but it’s worth it.
Cuban Coffee Queen – Best Coffee Stop. Ideal for a quick caffeine hit while exploring Old Town. Strong Cuban coffee, tasty breakfast sandwiches, and prime people-watching nearby.
Date & Thyme – Best for Healthy Breakfast or Lunch. A great option when you want something lighter. Think smoothies, fresh salads, wraps, and baked goods—perfect when you want to feel virtuous before the Duval Street decisions begin.
Island House Cafe – Best for Lunch & Poolside Vibes. One of our favorite lunch spots on the island—whether you’re staying at Island House or visiting with a day pass. The menu is surprisingly solid across the board, drinks are strong, and the open-air café makes it easy to settle in and socialize. Even non-guests are warmly welcomed.
Thirsty Mermaid – Best for Seafood Lovers. A local favorite known for beautifully prepared seafood dishes like yellowfin tuna and oysters. Cozy, intimate, and ideal for a slower-paced evening.
Nine One Five – Best for Upscale Dinner on Duval. A refined, romantic dinner option right on Duval Street. The menu leans toward elevated American cuisine with excellent cocktails—perfect for a night out before the bars.
La Te Da Restaurant – Best Dinner Before a Show. An absolute must. Whether you’re heading to Randy Roberts’ cabaret or just want a glamorous dinner, La Te Da delivers. We love dining poolside with martinis, fresh pastas, and polished service. Reservations are highly recommended.
Best Gay Bars & Clubs
Key West’s gay nightlife is wonderfully uncomplicated. Everything is centered around Duval Street, meaning you can bounce between bars on foot without ever needing an Uber. Nights here tend to start early, stay social, and often blur together with live music, drag shows, poolside cocktails, and casual dancing.
Instead of massive clubs, Key West thrives on open-air vibes, legendary personalities, and venues that feel like living rooms filled with friends. Here’s how to plan the perfect gay night out on the island:
La Te Da Cabaret – Iconic Shows & Glamorous Kickoff. Start your night at La Te Da with a cabaret performance by Randy Roberts—an absolute Key West institution. The intimate setting, campy humor, and polished performances make this the perfect way to ease into the evening before heading out onto Duval. Even if you’ve seen the show before, it’s worth seeing again.
Bourbon St. Pub – Lively, Social & Very Key West. Just a short stroll away, Bourbon St. Pub delivers classic island energy. Expect strong drinks, live music, male dancers, and nonstop people-watching. The crowd spills between the indoor bar and the open-air patio, making it one of the most social spots on Duval both day and night.
801 Bourbon Bar – Drag Shows & Dance Floor Energy. Drag is the main event here. Upstairs at 801 Bourbon Bar, nightly drag shows pack the room with high-energy performances and enthusiastic crowds. After the shows, the bar turns into a buzzing dance floor that stays lively well into the night.
Aqua Bar & Nightclub – Always Worth a Stop. Aqua is one of those places where something fun is always happening—drag, DJs, theme nights, or spontaneous dance parties. It’s right in the thick of Duval Street, making it easy to pop in and see where the energy is pulling you.
Saloon One – Relaxed, Local, No-Pressure Vibes. For something a little more low-key, Saloon One is a great reset stop. The crowd is friendly, conversational, and very local-heavy. It’s ideal for chatting with bartenders, meeting residents, or grabbing a drink between bigger venues.
Bobby’s Monkey Bar – Late-Night Drinks & Friendly Chaos. Casual, fun, and unpretentious, Bobby’s Monkey Bar is one of those places you didn’t plan to go—but end up staying longer than expected. It attracts a mixed LGBTQ+ crowd, stays busy late, and feels distinctly Key West in the best way.
When to Go
Key West is very much a vibe-based destination, and the best time to visit depends on whether you want peak energy, perfect weather, or fewer crowds and better deals. Here’s how the year breaks down:
Winter (Mid-November–Mid-April):
This is peak season in Key West, with warm, dry weather and nonstop activity. Expect blue skies, low humidity, and a full calendar of LGBTQ+ events, festivals, and nightlife. It’s the most popular—and most expensive—time to visit, with busy bars, packed guesthouses, and a lively social scene day and night.
Spring (April–May):
Spring is a sweet spot. The weather stays warm and sunny, but the crowds thin just enough to feel more relaxed. It’s ideal for pool days, sunset sails, and bar-hopping without the intensity of winter peak season. Prices are still strong but slightly easier to manage, especially after spring break.
Summer (June–September):
Summer brings heat, humidity, and a surprisingly fun energy thanks to major gay events like Tropical Heat and Bone Island weekends. Days are hot and sticky, but nights come alive with pool parties, theme nights, and a more locals-and-regulars crowd. Hotel prices drop, making this a great time for value-seekers who don’t mind tropical weather.
Fall (September–October):
Fall is the quietest season, with fewer visitors and some of the best hotel deals of the year. It’s also peak hurricane season, so travel plans should stay flexible. That said, when the weather behaves, Key West feels laid-back, intimate, and refreshingly local—perfect for travelers who prefer calm over crowds.
🌟 Pro tip – For major LGBTQ+ events, long weekends, and holidays, book as early as possible. Key West has limited inventory, and the best gay hotels sell out fast—sometimes months in advance.
Key LGBTQ+ Events in Key West
Key West may be small, but its LGBTQ+ events calendar punches far above its weight. Instead of massive city-wide Pride districts, events here feel personal, social, and immersive, with parties, pool days, and theme nights often centered around gay guesthouses, Duval Street venues, and the island’s famously relaxed, clothing-optional culture.
Event dates can shift year to year, so always double-check official event pages or hotel listings before booking — especially for peak weekends.
Key West Pride (June): Key West Pride brings classic Pride energy with an island twist. Expect colorful parades, pool parties, bar crawls, drag shows, and sunset gatherings spread across Duval Street and the historic Old Town. The vibe is celebratory but intimate, making it easy to meet people and feel part of the community rather than lost in massive crowds. June heat is real, but the party never slows down.
Tropical Heat (Late Summer): Tropical Heat is one of the biggest and most popular gay men’s event weeks in Key West, drawing visitors from across the U.S. and beyond. This multi-day event features daytime pool parties, themed nights, club takeovers, and after-hours fun — all packed into an island where everything is walkable. It’s hot, humid, and unapologetically sexy, with an energy that feels more like a private playground than a festival.
Fantasy Fest (October): While not exclusively LGBTQ+, Fantasy Fest is wildly popular with the queer community and one of the most iconic events in Key West. Think elaborate costumes, body paint, street parties, and a no-holds-barred atmosphere that blurs every line. Hotels sell out far in advance, bars overflow onto Duval Street, and the island feels gloriously chaotic for over a week. Many LGBTQ+ travelers time their visits specifically around Fantasy Fest for the over-the-top experience.
Bone Island Bare It All (December / July): This men-only, clothing-optional event celebrates Key West’s historic nickname, “Cayo Hueso” (Bone Island), and is all about freedom, body positivity, and social connection. Events typically include naked pool parties, theme nights, and guesthouse gatherings — with Island House at the center of much of the action.
🌟 Pro tip – We share behind-the-scenes coverage and what to actually expect during Bone Island Bare It All over on our Patreon.
Getting Here & Around
By Air: Fly into Key West International Airport (airport code: EYW) if you’re short on time.
By Car (Best road trip option): Fly into Miami (airport code: MIA) or Fort Lauderdale (airport code: FLL), rent a car, and drive the Overseas Highway all the way to Mile Marker Zero. It’s one of the most scenic drives in the U.S.
Getting Around: Once you’re on the island: walk, bike, or take short rides — Key West is compact and made for wandering.
🌟 Pro tip – Always carry travel insurance. We recommend SafetyWing to cover everything from lost luggage to unexpected medical expenses abroad.
Frequently Asked Questions & Travel Tips
Is Key West LGBTQ+ friendly?
Absolutely. Key West is one of the most LGBTQ+ welcoming destinations in the United States — and has been for decades. The island has a long history of gay travel, gay-owned businesses, inclusive guesthouses, and openly queer nightlife. From pool parties to drag shows to clothing-optional resorts, LGBTQ+ travelers aren’t just accepted here — they’re part of the fabric of the island.
Is there a gay neighborhood in Key West?
Key West doesn’t have a single defined gayborhood — instead, gay life is woven throughout the island. That said, there are two key hubs to know:
- Duval Street – This is where most of the gay bars, clubs, drag shows, and nightlife are concentrated, making it easy to bar-hop without ever calling an Uber.
- Fleming Street – Often called “gay guesthouse row,” this is where you’ll find iconic gay hotels like Island House and Alexander’s Guest House clustered together.
Between these two areas, you’re never far from the action.
Where is the gay beach in Key West?
There isn’t a traditional sandy “gay beach scene,” but here are your options:
Higgs Beach – The informal gay beach and is worth visiting for the Key West AIDS Memorial alone. It’s rocky and not ideal for lounging all day, but meaningful and important to see.
Zachary Taylor State Park – Hands-down the best beach on the island with crystal-clear water, scenic views, and history. If you want a real beach day, this is your best bet.
When is the best time to visit?
Best weather: Mid-November through mid-April — dry, sunny, and comfortable. This is peak season, so book early.
Best for events & high-energy gay weeks: Summer months, when events like Tropical Heat and Bone Island Bare It All take over the island. Just keep hurricane season in mind and stay flexible with plans.
How do I get around the city?
Key West is flat, compact, and easy to navigate by foot or bike. A car isn’t necessary once you’re on the island.
Is Key West safe for LGBTQ+ travelers?
Yes. Key West is generally very safe, relaxed, and welcoming for LGBTQ+ visitors. Violent crime is rare, and the island has a strong sense of community. As always, use standard awareness late at night, watch your belongings in crowded bars, and stay mindful after heavy partying — especially during major events.
Final Thoughts
Key West is fun, flirty, historic, and unapologetically itself — which is exactly why gay travelers love it. Whether you’re here for cabaret nights at La Te Da, day drinking by the pool at Island House, sunset rituals at Mallory Square, or a full Duval Street bar crawl that ends at “what time is it?” — Key West delivers.
🌟 Pro tip – Ready to plan your trip? Check out top Key West hotels, thrilling adventures on Viator, and don’t forget travel insurance with SafetyWing for peace of mind.
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