3* The Paradise Inn

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.

New Orleans House puts you about as close to Key West’s gay nightlife as physically possible: it sits right on Duval Street, directly above and around the Bourbon Street Pub complex. This is very much a gay men’s guesthouse rather than simply an LGBTQ-friendly hotel. The clothing-optional garden bar, pool, hot tub and sundecks create a sociable atmosphere throughout the day, while Bourbon Street Pub and 801 Bourbon give you drag, dancers and late-night entertainment without even having to cross the street. That convenience does come with an obvious warning: some rooms are above the dance floor and the party can continue until 4am. Quieter rooms are available, so say so when booking if sleep matters. GayMapper tip: unbeatable for gay nightlife if you want the party quite literally downstairs — just choose your room carefully if you don’t intend to join it every night.

The Saint Hotel Key West, Autograph Collection, Adult Only takes a rather more playful approach to boutique luxury. The interiors are bold, the atmosphere is deliberately grown-up and the slogan — “play naughty, sleep saintly” — tells you roughly where they’re going with it. The Eaton Street location puts you just off Duval, close to Mallory Square and the waterfront while keeping the gay bars within easy walking distance. There’s also nightly live music at the rooftop lounge, so you don’t have to immediately head back out after dinner. Rooms vary considerably in size, with some intentionally compact European-style options, so it’s worth checking exactly what you’re booking. GayMapper tip: a fun choice if you want boutique luxury with a bit of attitude rather than traditional Key West prettiness.

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.

The Paradise Inn hides just off Duval Street behind tropical gardens, ponds and old Key West cottages, giving you a surprisingly peaceful base considering how central you are. Walk a few minutes and you’re amongst the bars and restaurants of Duval, with The Bourbon Street Pub complex and the main gay nightlife comfortably within reach. The Hemingway House and Southernmost Point are equally easy during the day, so there’s little reason to bother with a car. This is an adults-only stay, with a pool, hot tub and afternoon wine-and-cheese hour adding to the relaxed atmosphere. GayMapper tip: a good middle ground if you want Duval Street close enough for spontaneous nights out but don’t necessarily want to sleep directly on it.

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.