4* The Saint Hotel Key West

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.

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 Gardens Hotel is one of those places where stepping through the gates feels like leaving Duval Street behind, even though it’s only a block away. The lush grounds, historic rooms and cottages create a much quieter, more romantic atmosphere than most central Key West hotels, while the self-serve wine gallery and regular live music give evenings at the hotel a little personality of their own. Staff and service consistently get particularly warm feedback. When you do head out, the gay bars, restaurants and rest of Old Town are all comfortably walkable. GayMapper tip: a great choice for couples who want a more polished, romantic Key West stay without giving up easy access to the gay scene.

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.

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.