Where to stay in Key West
The gay guesthouses sit in Old Town's leafy lanes, within walking or biking distance of the Duval Street bars, and most have pools and happy hours. December to April has the best weather, and Fantasy Fest (late October) and New Year's Eve sell out early.
New Orleans House
Duval St, Old Town
A gay men's guesthouse right above the Bourbon St. Pub, with a 24-hour pool, a 15-person jacuzzi, a backyard garden bar and a balcony over Duval. Breakfast is included, and it's for men who want to be in the middle of the nightlife.
Official siteLa Te Da
1125 Duval St, Old Town
A historic Duval Street hotel for guests 21 and over, with a pool, a piano bar and a nightly drag cabaret downstairs. It's a fun, central choice for friends who want shows and dinner without a taxi.
Official siteIsland House
Fleming St at White St, Old Town
Open since 1976, it calls itself the oldest operating gay men's resort in the world. It has a big heated pool, a gym, a sauna, a 24-hour cafe and bar, and a daily happy hour that's the social event of the day.
Official siteAlexander's Guesthouse
1118 Fleming St, Old Town
A historic three-story conch house for guests 21 and over on a quiet, shady street, describing itself as LGBTQ+ friendly. Expect an expanded breakfast, a 24-hour pool and spa, three levels of sun decks and a daily poolside happy hour.
Official sitePlan around these
Fantasy Fest
Key West, FL · Oct 16–25, 2026
Ten days of adult costume chaos on Duval Street. The big parade is Saturday, Oct 24.
Key West Pride
Key West, FL · Dates TBA TBA, early June (2026 was Jun 3–7)
Island Pride with a Duval Street parade and pool parties.
Fantasy Fest
Key West, FL · Oct 22–31, 2027
Ten days of costumes on Duval Street.
Listings checked against official sites in 2025–26. Policies and prices change, so confirm before you book. We don't take money from hotels.