Key West Gay Resorts: The Men-Only and Mixed Guesthouses Open in 2026, and the Ones That Closed

Last updated: October 17, 2026 · By Joe Ghafari, CEO of Visiting Wrld

The short answer: Two men-only, clothing-optional gay guesthouses are open in Key West in 2026: Island House on Fleming Street and New Orleans House on Duval Street, upstairs from Bourbon St. Pub. For a mixed group, Alexander's Guesthouse and La Te Da are gay-run and welcome everyone. Past those four, you are choosing a gay friendly mainstream hotel. The Equator Resort, the third men-only name on older lists, closed in January 2025, and several other famous gay guesthouses were sold and changed years before that.

We run gay men's retreats abroad, not hotels in Florida, so nobody on this page paid to be here. This is the long version of the Key West section in our guide to the best gay resorts in the USA. It covers every gay guesthouse we could confirm is open, the rules at each one, the gay friendly hotels worth a look, the names that closed or changed, where to go out, and when to go.

How gay Key West is laid out

Key West is small. Old Town, where nearly everything in this guide sits, is easy to cross on foot or by bike. Two streets do most of the work.

• Fleming Street is where you sleep. Island House describes its corner as "gay Guesthouse Row." Island House and Alexander's are on the same block of Fleming, a few blocks east of Duval, and the Equator was on Fleming too.
• Duval Street is where you go out. The gay stretch runs roughly from the 700 block to the 900 block, where Bourbon St. Pub, New Orleans House and 801 Bourbon Bar sit within a few doors of each other. La Te Da is further up, at 1125 Duval, on the quieter end.

The guesthouses are old wooden houses and cottages around a pool. Island House, the biggest, has 39 rooms. By the second breakfast you recognize most of the other guests. Nobody sells an all-inclusive plan here. You get a room, usually breakfast, often a happy hour, and the town does the rest.

The men-only gay guesthouses open in 2026

Island House. On the corner of Fleming and White Streets, about six blocks from Duval. It has been a clothing-optional resort for gay men from 1976 on, so 2026 is its 50th year. There are 39 rooms, a large heated pool, a poolside café and bar open around the clock, a 24-hour gym, a steam room and a dry sauna, two big jacuzzis (one indoors, one out), massage, and a misted sundeck. Clothing is optional everywhere on the resort side except the gym, where state law wants shoes and shorts. Registered guests get a daily happy hour from 5 to 6:30 p.m. The Hot Naked Humpday pool party on Wednesdays and Hot Naked Sunday are the two fixed points of the week.

One detail older guides miss. Island House also rents detached units across Stickney Lane, where women and other guests can stay, and those guests do not get into the clothing-optional compound. The compound itself stays men only.

Book Island House if you want a social week and you are relaxed about nudity and about what happens around a gay men's pool after dark. It does not pretend to be a quiet inn, and we like that about it.

New Orleans House. The only gay men's guesthouse on Duval itself, at 724, upstairs from Bourbon St. Pub and part of the same complex. It has a large clothing-optional back garden with the Garden Bar open until 4 a.m., a 24-hour pool, a 15-man jacuzzi, a second-floor sundeck, a gym for guests and a continental breakfast. The pub advertises its pool and jacuzzi as male only and clothing optional. The guesthouse website also says "all-welcome accommodations available," so if you are booking for a mixed group, call and ask which rooms that covers.

You are sleeping on top of a bar complex, and the noise comes with the room. Pick New Orleans House if you plan to be out every night and want a two-minute walk home. Pick Island House if you want the pool to be the main event.

The mixed LGBTQ+ guesthouses

Alexander's Guesthouse. At 1118 Fleming Street, on the same block as Island House. Its own line is "Everyone is welcome. We are proud to be Adult Exclusive, LGBTQ+ Friendly," and every guest must be at least 21. There is a pool and a jacuzzi, an expanded continental breakfast, and a daily happy hour with complimentary cocktails that does a lot of the introductions. The website says nothing about clothing optional and travel guides disagree, so pack swimwear and ask if it matters to you. If your group includes women, this is the one to book.

La Te Da. A historic hotel, bar and cabaret at 1125 Duval Street, in an 1892 building where José Martí gave speeches from the second-floor balcony. Travel guides describe about 15 adults-only rooms around a pool. The draw is the stage: Randy Roberts Live, a drag show where every note is sung live, runs in the cabaret, and guides list a Sunday tea dance by the pool. It is not men-only and it is not clothing optional. Stay here for the shows, or stay anywhere and walk up for dinner and a performance.

Gay friendly hotels in Key West

If the guesthouses are full, or you want a mainstream hotel that treats a gay couple like any other couple, these are the names LGBTQ+ travel guides keep returning to. We could not confirm that any of them is gay-owned, and none is clothing optional.

• The Marquesa Hotel. A boutique hotel at 600 Fleming Street, one block off Duval, in restored Victorian houses around garden pools. Calm, central and walkable to everything.
• Key West Historic Inns. Five small inns: Ridley House, Winslow's Bungalows, Ella's Cottages, Lighthouse Hotel and Fitch Lodge. These are the Key West inns that used to carry the Kimpton name before they left IHG in January 2024, so do not search for them under Kimpton anymore. Ridley House, spread over three historic homes a few blocks from Duval, is the one gay travel writers mention most.
• Simonton Court. A two-acre compound of cottages and rooms built around an 1880s cigar factory, with several pools. A good pick for a couple who wants quiet.
• The Gardens Hotel. A small Old Town hotel set in large tropical gardens, with two pools.

Closed or changed: the names on old lists

Key West has fewer gay guesthouses than it did twenty years ago. Old articles and forum threads still send people to places that closed or stopped being gay guesthouses long ago. Here is where each one we checked stands.

• Equator Resort: closed. The men-only, clothing-optional guesthouse on Fleming Street closed on January 9, 2025, after 28 years. Management said the property was not being sold and the family company was shifting its focus.
• Coral Tree Inn: closed with the Equator. The 11-room inn was sold in December 2012 and became part of the Equator, so it went when the Equator did.
• Oasis Guest House: no longer a gay guesthouse. The Oasis on Fleming Street was sold and opened to all guests in October 2012.
• Big Ruby's: no longer a gay guesthouse. The men-only, clothing-optional guesthouse on Applerouth Lane was sold in 2013, went all-welcome that November, and now runs as The Cabana Inn.
• Pearl's Rainbow: no longer a women's guesthouse. Key West's best-known lesbian guesthouse, on United Street, opened to men in November 2010 and was sold in 2013. The building is a general adults-only inn under another name today.
• Lighthouse Court: now the Lighthouse Hotel. Its current owners say it became one of Key West's first LGBTQ guesthouses in the 1980s. Today it is one of the mainstream Key West Historic Inns above.

If a page still tells you to book any of these as a gay stay, look at when it was written.

Key West gay guesthouses compared

Two labels decide your week more than the room does. Men-only is about who can book. Clothing optional is about where you can be naked, and it can mean the whole property or just the pool. They often come together in Key West, but not always, and nobody makes you undress. Ask where exactly the rule applies before you pay.

Property	Where	Who stays	Clothing optional?	Best for
Island House	Fleming St, Guesthouse Row	Men only (compound)	Yes, whole resort side except the gym	A social week, pool parties
New Orleans House	724 Duval St	Gay men; some all-welcome rooms	Yes, back garden, pool and jacuzzi	Going out every night
Alexander's Guesthouse	1118 Fleming St	Everyone, 21 and up	Not advertised	Mixed groups, groups with women
La Te Da	1125 Duval St	Everyone, adults only	No	Cabaret and a quieter end of Duval
The Marquesa Hotel	600 Fleming St	Everyone	No	A calm couple's stay
Key West Historic Inns	Old Town, five inns	Everyone	No	Small inns, ex-Kimpton

Where to go out in gay Key West

The gay bars sit a few doors apart, so a night out is a walk, not a plan.

• Bourbon St. Pub, 724 Duval. Five bars, a video bar with dancers, a garden bar, and the male-only, clothing-optional pool and jacuzzi out back. Same complex as New Orleans House.
• 801 Bourbon Bar, 801 Duval. Drag every night from the 801 Girls, with shows at 9 and 11 p.m., plus karaoke on Sunday afternoons.
• La Te Da, 1125 Duval. Cabaret with live vocals and a piano bar, further up the street.
• Aqua: closed. The drag club and nightclub at 711 Duval closed on July 6, 2026, after its operator was evicted. 22&Co, in the same complex on Angela Street, was still open in late July, and the Birdcage cabaret beside it had announced final shows, so call before you go.

In the daytime, Higgs Beach on the Atlantic side is the one LGBTQ+ travel guides call the unofficial gay beach.

Key West gay events by season

Four weeks of the year change the island. The gay guesthouses fill first for every one of them, so book early if your dates overlap.

• Fantasy Fest, the second half of October. Ten days of costume parades, masquerade balls, body paint and a mile-long street fair on Duval. The 2026 edition runs October 16 to 25, with the theme "Musical Icons and Iconic Musicals" and the main parade on the evening of Saturday, October 24. It is a whole-island party rather than a gay event, and it is firmly for adults.
• Key West Pride, early June. Five days of parties, a street fair and a parade on Duval. The 2026 edition ran June 3 to 7. Check Key West Pride's own pages for next year's dates before you book.
• Tropical Heat, mid-August. Five days for gay men 21 and up: themed parties, pool parties and clothing-optional events, several at Island House and Bourbon St. Pub. The 2026 edition ran August 12 to 16.
• Womenfest, early September. Still going, five days for women with pool parties, music and boat trips. The 2026 edition ran September 2 to 6.

Look at those months again. Tropical Heat, Womenfest and Fantasy Fest all fall inside hurricane season, which is the next thing to plan around.

Getting there, and hurricane season

Flying in. Key West International Airport (EYW) is on the east side of the island, a short drive from Old Town. American, Delta, United, JetBlue, Silver Airways, Allegiant and Avelo all fly there. Routes change, so check the airport's airline page for current nonstops.

Driving down. Plenty of people fly into Miami or Fort Lauderdale and drive. The Overseas Highway, the last 113 miles of US 1, runs down the Keys over 42 bridges, including the Seven Mile Bridge. From Miami, allow around four hours, and more on event weekends. If you are flying through Fort Lauderdale anyway, our guide to gay resorts in Fort Lauderdale covers a night or two there first. Ask your guesthouse about parking before you bring a car into Old Town.

Hurricane season. The Atlantic season runs from June 1 to November 30. The National Hurricane Center puts the peak on September 10, with most activity between mid-August and mid-October. In 2005, damage from Hurricane Wilma pushed Fantasy Fest back to December. If you are going in those months, buy travel insurance that covers hurricanes, read the guesthouse cancellation policy before you pay, and watch the forecast the week before you fly. December through May sits entirely outside the season.

Which Key West gay guesthouse fits your trip

• Going alone and want to meet men: Island House. The pool parties do the introductions for you. Our guide to the best gay vacations for single men covers solo trips further afield.
• Out every night: New Orleans House, or Island House if you want the pool too.
• A mixed group or friends who are women: Alexander's, with La Te Da for a night out.
• A couple who wants quiet and swimwear: the Marquesa, Simonton Court or one of the Key West Historic Inns.
• Timing a trip around an event: Fantasy Fest in October, Pride in June, Tropical Heat in August, and book the room before the flight.

A guesthouse weekend or a week with a group

Key West makes a very good gay long weekend. The bars are a few doors apart, the guesthouses are friendly, and at Island House you will not be short of company. What you cannot choose is who else booked the same dates.

What we run is a different trip, and we would rather say so than pretend it competes with Duval Street. A Visiting Wrld retreat is six to nine days abroad, in Costa Rica, Mexico, Bali or Thailand, in a villa with a group of gay men who all applied for the same week. Mornings are coached training at the gym. Afternoons are the destination, including a private yacht day with snorkeling. Evenings are dinner together. Most of the men arrive solo, so being the new guy is normal from the first dinner.

If you are weighing the two, our comparison of gay resorts vs gay retreats goes through the trade-offs, gay fitness retreats has the destinations, and our solo travel guide is for the man who is not sure about going alone.

Sources: each property's own website (Island House, its FAQ, New Orleans House, Bourbon St. Pub, Alexander's, La Te Da, the Marquesa, Key West Historic Inns), Nomadic Boys on Key West gay resorts (updated June 2026), Out x Out on Key West hotels and its Key West guide (both updated August 2026), Out x Out on the Aqua closure (July 2026), the Key West Chamber on the Equator closure, the Key West Chamber on Fantasy Fest 2026, on Key West Pride 2026 and on Tropical Heat 2026, Key West Citizen on Womenfest 2026, Pride.com on Pearl's Rainbow, a 2013 record of Key West guesthouse sales, the National Hurricane Center, and Key West International Airport, all read on September 14, 2026.