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Key West has long been a refuge for those rebelling against imposed social norms, and the adults-only, clothing-optional Island House remains a testament to the island’s progressive, free-spirited ethos. Cloaked in dense foliage at the edge of Old Town, the resort caters specifically to gay men, with a large pool and surrounding bar at its center, plus a sundeck, multiple hot tubs, steam room, sauna, and fitness center. Most rooms were renovated in 2024, trading an old Florida look for something more contemporary, though accommodations still vary widely in size and style, from small queens with shared baths to apartments with full kitchens, private porches, and dedicated parking. In early 2026, the resort debuted its most ambitious accommodations to date: Island Mates Manor, a pair of three-story villas offered as month-long luxury vacation rentals rather than nightly stays. Each has a chef’s kitchen, extensive custom woodwork, two king suites, 2.5 baths, private balconies, built-in desks, and a washer and dryer; the villas share a pool with in-water ledge loungers and a six-person hot tub. Villa guests also have access to all Island House amenities, including its 24-hour outdoor café and bar and four complimentary alcoholic drinks during daily happy hour. Duval Street’s bars and restaurants are about a 15- to 20-minute walk away, including LGBTQ+ favorites 801 Bourbon Bar, One Saloon, and Bourbon Street Pub.
