Island House Key West Resort

"Why book? Key West has long been a refuge for those rebelling against imposed social norms and, as such, has reigned a popular destination for the gay community since the 1970s. While most resorts nowadays in Key West are predictably mainstream and family-friendly, the adults-only, clothing optional Island House Resort Key West is still testament to the island’s progressive, free-spirited ethos. If you’re not a gay man, look elsewhere; but if you are and desire a vibrant 39-room resort with hedonistic overtones, you’ll want to reconsider your heteronormative hotel choices and check into the Island House. Set the scene Cloaked in dense foliage at the edge of Old Town Key West, the Island House is a haven for gay men, looking for comradery (and more) as part of a tropical vacation. A large pool and surrounding bar anchor the boutique property, around which you’ll find a sundeck, multiple hot tubs, and a fitness center (where clothes are required.) The House’s architecture was inspired by Ernest Hemingway’s Havana home. The backstory In 1999 entrepreneur, philanthropist, and community trailblazer Jon Allen purchased a neglected Key West guest house and transformed it into a fabulous gay men’s resort. Soon after, gay-centric publications were raving about this newfound oasis of sun-kissed, clothing-optional, unapologetic fun—and gay men arrived in droves. Today, Island House is better than ever thanks to major renovations in 2023, which gave most rooms fresh and handsome new looks. The rooms Rooms vary in shape and size, ranging from small queen rooms with shared baths to luxury apartments located across from the main house with full kitchens, private porches, and dedicated parking. There are a total of 39 units, most of which have been renovated as of 2024, swapping an old Florida aesthetic for something more contemporary island chic. Do enquire about the room’s renovation status at booking to ensure it meets your style requirements. Food and drink A covered 24-hour outdoor café and bar overlooks the swimming pool. Expect solid gastropub selections (read: don’t ditch your outside dinner reservations to eat here but also don’t fret if you’re too occupied to leave the property for a meal.) All registered guests get four free alcoholic drinks during the daily happy hour from 5:00-6:30pm. The spa There’s an outdoor cabana for spa treatments. Indoors, find a steam room, sauna, hot tub, and fitness center. The neighborhood/area At the edge of Old Key West, Island House Key West is found among the island’s residential cluster of historic homes and inns along Fleming Street. The bars and restaurants of Duval Street are about a 15-20 minute walk away (less than a mile) and that includes gay favorites 801 Bourbon Bar, One Saloon, and Bourbon Street Pub. The service Front desk staff, bartenders and wait staff are attentive and affable across the board. Accessibility While there are no elevators, the ground floor of the Island House, including the cafe, is wheelchair accessible. Select guest rooms with wider door frames allow for wheelchair access. Anything left to mention? Island House targets a niche market and is not for everyone. Gay men with a penchant for clothing-optional environments will want to check it out; others should look elsewhere." - Paul Rubio