4* The Gardens Hotel

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.

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.

La Te Da is one of those rare hotels where staying in can be just as entertaining as going out. The historic property sits directly on Duval Street and combines just a handful of rooms with Christopher’s restaurant, bars and a long-running cabaret programme. Randy Roberts’ live show remains a Key West institution, so evenings can easily begin downstairs before wandering into the rest of the gay scene. Bourbon Street Pub and 801 Bourbon are only a short walk away, while the Southernmost Point and Hemingway House are equally convenient during daylight hours. La Te Da is strictly 21+, and the atmosphere feels grown-up and sociable rather than resort-like. GayMapper tip: perfect if you like the idea of dinner, cocktails and cabaret all under one roof, with the rest of Duval Street waiting outside when you’re ready.

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.

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.

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.