From Miami, Key West is a scenic 3.5-hour drive down Florida’s Overseas Highway (US 1). Upon arriving in the Conch Republic, you’ll find a laid-back, eclectic and alternative community that has been a safe haven for LGBT travelers, artists and free thinkers since the early 1970’s. One of the first global gay travel destinations, this small island is a place were gay locals and visitors feel at home among the majestic palm trees, turquoise waters, breathtaking sunsets and rainbow flags. After the nightly Sunset Celebration at Mallory Square, make way to the parties on Duval Street at gay hangouts like 801 Bourbon Street for drag shows or Bourbon Street Pub for dancing. Besides a few other destinations in the US like Palm Springs, Provincetown and Fort Lauderdale, Key West is among these top cities with the most gay and clothing options resorts in the country.

With its tropical climate, you can expect year-round warm weather making it an ideal destination for sun, sea, sand and sex any time of year. However, the high season is from December to March when many escape the cold, winter weather up north. Join the flocks of gays for annual celebrations and events like New Year’s Eve, Key West Pride in June, Tropical Heat in August and Women Fest over Labor Day Weekend. No matter when you visit, you’ll want to stay close to the action and there are plenty of hotels, resorts and cute beach houses to choose from. But for those who specifically want a gay property and perhaps even a clothing optional resort, we narrowed down the list to our top 5 gay hotels and resorts in Key West.

Clothing Optional Gay Hotels and Resorts in Key West

Island House – Award-winning clothing-optional resort for gay men. The property has a large poolside café and bar and they regularly host social events onsite. The hotel offers a gym with sauna, steam room and multiple Jacuzzis.

Photo credit: Island House

Alexander’s Guest House – Beautiful grounds located in a quiet neighborhood and just a minute from Duval St. Alexander’s Guesthouse is proudly gay-owned and operated.

New Orleans House – the only gay, all-male guesthouse on Duval Street, right in the heart of all the Old Town action.

Equator Resort – gay-owned guesthouse tucked away in the heart of Old Town. The resort offers a large, lush and open private setting with two heated pools and two hot tubs. Comprised of five historic properties, each room is unique and offers its own charm all with private baths and spacious.

Apartments

There are many sites for apartment rentals in Key West, with AirBnB probably being one of the most popular. Prices are generally comparable to budget hotels, especially if you’re willing to get a room in a shared apartment. Book AirBnB →

There are even a few LGBT-oriented booking sites like misterb&b with listings from gay hosts for gay guests where you can either rent a whole apartment or a private room in a shared apartment. Understanding Key West’s gay scene is much more easily done with the help of a local and apartment sharing is one of the best ways to meet someone living in the city who knows how things work, where and when are the best nights to go out, and what places to eat at and which to avoid.

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