Gay 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 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.

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.

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.

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.