Island House Key West

Island House suits gay men who want a social, self-contained resort where the pool, bar, gym and steam room are all on site. Mixed groups should note how it handles other guests: the clothing-optional side is for men only.

What sets it apart

Island House describes itself as “a clothing optional sanctuary for gay men since 1976.” Clothing is optional throughout the clothing-optional side; Florida law requires shorts and shoes in the gym. Guests register at the front desk and visitors are buzzed in.

The facilities are what most guests come for: a heated pool with a misting system, a 24-hour poolside cafe and bar, and a 24-hour health club with a steam room, dry sauna and two large jacuzzis. Massage therapists work on site. Registered guests get a daily happy hour from 5 to 6:30 pm with four free drinks, and the resort holds pool parties on Wednesdays and Sundays.

Traveling with women or mixed groups

Non-male guests are not allowed on the clothing-optional side. They can stay in the resort’s separate luxury apartments across Stickney Lane, which have their own cafe. For an LGBTQ+ guesthouse that takes everyone in the same building, see Alexander’s on the same street.

Where it is

1129 Fleming Street in Old Town, per independent hotel listings; the resort’s contact page gives only phone and email.

Rates and cancellation

The rooms page lists eleven room and apartment types at $369–769 a night for two, from a standard room with a shared bath to a poolside owner’s suite. Extra guests pay $50 a night. Two villas nearby are rented monthly, 30 nights minimum.

Cancellations must be made by phone. Cancel at least 15 days before arrival and the deposit is refunded minus a $50 fee; inside 15 days the deposit is forfeited. Holidays and Fantasy Fest carry special terms, explained at booking. The resort’s site does not describe day passes.

What recent guests say

Tripadvisor showed 737 reviews averaging 4.6 in October 2026. These themes came up repeatedly:

Paraphrased from Tripadvisor reviews, October 2026.

How it compares

Choose New Orleans House to stay on Duval Street itself, with a clothing-optional backyard and a bar open until 4 am. Choose Alexander’s for a quieter, adults-only guesthouse open to every gender. In Fort Lauderdale, The Worthington is the closest match for a big, social crowd, and Pineapple Point for a quieter stay.