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Key West Gay Cruising

Discover where to find the gay cruising action in Key West, Florida. GayMapper has all the information about the gay cruising spots in and around the city. As always, be conscious of your personal safety when meeting strangers.

Key West Hotel Deals

Grab a great deal on your trip with GayMapper's hotel partners

Alexander's Guesthouse has been welcoming LGBTQ+ travellers to Key West for years, and the friendly, personal atmosphere is still the reason we like it so much. The gay-owned guesthouse occupies a cluster of beautifully restored Conch houses on a quiet Old Town street, around ten minutes on foot from Duval. Breakfast and the daily complimentary happy hour naturally bring guests together, while the pool, hot tub and sun decks give you plenty of space to relax without the feel of a large resort. Solo travellers tend to find it especially easy to meet people here. You’re close enough to walk to the nightlife but far enough away that Fleming Street stays pleasantly residential. GayMapper tip: our favourite if you want a genuinely LGBTQ-centred stay that feels friendly and sociable without becoming a party resort.
Simonton Court Historic Inn & Cottages spreads across a wonderfully lush collection of old Key West buildings, including former cigar workers’ cottages, historic houses and hidden garden paths. Despite the secluded feel, Duval Street is only a block away and Mallory Square is an easy walk, so you can leave the hotel in almost any direction and find restaurants, bars or something worth seeing. The gay nightlife around central Duval is close enough for an easy walk home afterwards. Four pools are scattered around the grounds, which helps the property feel intimate despite being larger than many Old Town inns. GayMapper tip: especially good if historic Key West atmosphere matters to you but you still want the nightlife and waterfront firmly within walking distance.
NYAH Key West works particularly well for friends travelling together, especially in a destination where hotel prices can become fairly alarming. Rooms can sleep several people in individual beds, so nobody has to draw the short straw and spend the weekend on a sofa. You’re in Old Town rather than directly on Duval, but the bars, restaurants and nightlife are only a few blocks away and almost everything central is walkable. Three pools and a hot tub make the communal areas sociable without turning the place into a full-on party hostel. The hotel is adult-only and attracts groups, so expect a livelier atmosphere than at Key West’s romantic boutique inns. GayMapper tip: a smart choice for a group trip when splitting a room makes more sense than everyone paying Key West prices separately.
Ridley House feels far more like staying in an elegant old Key West home than checking into a conventional hotel. The historic buildings sit on Caroline Street in Old Town, surrounded by porches, tropical greenery and a small pool hidden away behind the house. Duval Street is only a block away, but you’re towards the quieter northern end, which means Mallory Square, the waterfront and plenty of restaurants are particularly handy. The gay bars further south on Duval are still easily walkable. The small scale and residential feel suit Key West perfectly, especially if you want character without sacrificing location. GayMapper tip: a lovely couples’ choice if you want Old Town charm and easy access to nightlife but would rather come home to somewhere calm.

Cruising Bars in Key West

One Saloon

One Saloon

Older Crowd, Fetish, Outdoor Seating, Cruising

This unassuming place located in the Bourbon Bar complex is the only male only leather bar in the city, catering to a super masculine and pretty cruisey crowd. There's a dungeon to explore, regular themed nights, drinks specials, and a welcoming atmosphere that lets you party however you like until late. Every Friday at midnight the bar hosts "Cock Shot".
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Bourbon Street Pub

Bourbon Street Pub

Drag, Outdoor Seating, Dancers, Cruising

Key West's original and only video bar brings a New Orleans inspired space to this small-town gay scene. The venue includes a male only garden bar where clothing is optional, and you'll find guys hanging out by the pool or in the jacuzzi. See what's on in the theatre space or head inside for one of the other bars. There are regular themed nights, drag shows, and cute dancers to entertain a mostly male crowd.
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Other Cruising Spots in Key West

Island House Key West

Island House Key West

Men Only, Cruising

Island House is a private, male-only, and clothing-optional resort in Old Town Key West. It features a beautiful poolside cafe and bar, heated pool, and jacuzzis. Inside there are luxury rooms, so stay and enjoy a full gym, sauna, steam room, and video lounge. It's no surprise that Island House has been consistently named 'the best gay men's resort in the world" and is a favourite cruising spot for local gay guys. If you're not staying at the hotel, it's possible to purchase a day pass to access the clothing optional pool, bar and spa areas.
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Smathers Beach

Smathers Beach

Mixed Ages, Cruising

Located close to Duval Street where much of the gay life is in Key West, you'll find Smathers Beach. It's possibly the most popular beach with the gay crowd in the area, but the crowd is mixed and be aware that public nudism is illegal, so keep your trunks on! The beach is just over two miles long and gets busy with a wide variety of guys and gals.
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Tours & Experiences in Key West

Key West has always had a taste for eccentricity, which is precisely why it works. Visit the Hemingway Home, pose at the Southernmost Point or head out on a sunset cruise, then wander back towards Duval Street and see where the evening takes you.


Gay friendly hotels in Key West

Key West is compact and wonderfully easy to explore, so staying in Old Town puts most of what you’ll want within walking distance. Duval Street and the surrounding streets are home to much of the island’s gay nightlife, restaurants and entertainment, with the waterfront and major attractions nearby too. GayMapper’s recommended hotels include gay and LGBTQ+ friendly guesthouses, adults-only stays, characterful historic properties and more luxurious escapes – perfect whether you want to join the party or disappear behind a palm tree for a few days.

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