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 LGBTQ+ travelers, artists, and free thinkers since the early 1970s. One of the first global gay travel destinations, this small island is a place where 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, head to the parties on Duval Street at gay hangouts like 801 Bourbon Street for drag shows or Bourbon Street Pub for dancing. Aside from a few other destinations in the U.S., such as Palm Springs, Provincetown, and Fort Lauderdale, Key West is one of the top cities with the most gay and clothing-optional 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 at 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 specifically wanting a gay property—and perhaps even a clothing-optional resort—we’ve narrowed down the list to our top 5 gay hotels and resorts in Key West.

Why Stay at a Gay Resort in Key West?

The concept of LGBTQ+-specific travel started in the 1970s and was pioneered by Hans Ebensten, who began taking gay men on tours rafting through the Grand Canyon and to Carnival in Rio de Janeiro. As LGBTQ+ people became more visible and acceptance grew, several companies began creating trips specifically for the LGBTQ+ community. The concept of a gay hotel or men’s gay resort was also born around the same time in Key West, Florida. Small gay resort towns became popular in the ’80s and ’90s in places like Palm Springs, Fort Lauderdale, and Provincetown.

If you’ve never stayed at a gay resort but are thinking about booking one, you should definitely consider some of these benefits below:

Easy to meet new people – Most gay resorts offer social activities where you can meet other travelers, which is common in many of the gay resorts in Key West. Most properties host a complimentary evening happy hour offering beer, cocktails, and snacks. You can spend the afternoon meeting other guests and easily connect with other guys during your visit.

Location – Most gay guest houses in Key West are well-located within or near the gay area of Duval Street, between Angela and Petronia Streets. This is where you’ll spot rainbow crosswalks and can easily visit the most popular gay bars and nightlife.

Parties and events – Some gay resorts in Key West host events or other parties and social gatherings at their properties. These activities might be offered just to guests, or in some cases, even to the local LGBTQ+ community.

Be yourself – One of the most attractive aspects of a gay guest house is the comfort zone. The entire place is full of LGBTQ+ guests, and the staff has been extensively trained to provide a welcoming and gay-friendly experience. It’s a very open environment where you can relax and be yourself.

Clothing Optional Gay Hotels and Resorts in Key West

Island House Key West – Luxury Playground in Paradise

A gay guest house since 1974, the current owners purchased the property in 1999 and completely renovated the complex. Now it’s an award-winning, clothing-optional resort for gay men and one of the most popular in Key West. There is a wide variety of well-appointed guest rooms, suites, and apartments that are perfect whether you are traveling solo or with a group. All rooms are private and have a clothes-hanging rack, luggage storage, small bureau, USB alarm clock, electronic safe, ice bucket, and small refrigerator. Some rooms have shared baths, while others are private. The property is a 4-star resort offering great amenities and services, including a large poolside café and bar, and regularly hosts social events onsite. The hotel also offers a 24-hour gym with a sauna, steam room, and multiple Jacuzzis. Island House has won a variety of awards from BOYZ and Out Traveler magazines, as well as top recognition from TripAdvisor.

Alexander’s Guest House – Island Oasis Boasting Tropical Elegance

Located on a quiet neighborhood street in the heart of Key West’s Old Town, this beautifully restored Key West Conch house, built in 1902, is proudly gay-owned and operated. The elegant yet modern and comfortable suites and guest rooms feel like a home away from home, featuring private baths, air conditioning, flat-screen TVs, mini-fridges, and modern amenities. The grounds are a stunning oasis of tranquility, featuring a pool, jacuzzi, sun loungers, clothing-optional sun decks, delicious breakfast, and a friendly happy hour with complimentary cocktails. When it’s time to head out for dinner and a night on the town, you’re just minutes from Duval Street and all the action.

New Orleans House – No-frills Guest House on Duval Street

This is the only gay, all-male guesthouse on Duval Street. You literally couldn’t be any closer to the Old Town party scene. In fact, it's in the same complex as the popular Bourbon Street Pub, Key West’s original and only video bar featuring the Men of Bourbon nightly, live DJs and shows, five bars, and a male-only clothing-optional garden bar with a pool and jacuzzi. Guests are granted complimentary access to the Bourbon Street Pub and the drag shows at 801 Bourbon every night, as well as the grand balcony overlooking Duval Street—a prime spot to enjoy a coffee, cocktail, or people-watch. Accommodations include a dog-friendly cottage, one-bedroom apartment, and a variety of simple and comfortable guest rooms, some of which have small kitchens and balcony access. All rooms have free Wi-Fi, cable TV, air conditioning, ceiling fans, refrigerators, coffee makers, and microwave ovens. Amenities include a clothing-optional sundeck, pool, 15-person jacuzzi, gym, complimentary happy hour every evening, and a continental breakfast every morning. Two on-site restaurants, Red Shoe Island Bistro and Pizza Joe’s, offer an array of tasty Key West eats and drinks.

misterb&b – A Home Away From Home

If you’re looking to live like a gay local when you visit Key West, check out the hundreds of accommodations available on Misterb&b. Founded in 2014, misterb&b is not a hotel chain but an LGBTQ+-oriented booking site with listings from gay hosts for gay guests, where you can rent a whole home, apartment, or private room in a shared apartment. They have hosts in more than 200 countries and territories with over 1 million total listings.

Understanding Key West’s gay scene is much easier with the help of a local, and apartment sharing is one of the best ways to meet someone who knows how things work—where and when the best nights are to go out, and what places to eat at and which to avoid. Also, renting an entire home or apartment offers additional privacy and convenience, providing a relaxing escape from the gay party scene and nightlife.

Special Offer! Sign up with misterb&b  and you will receive a free $10 credit to use on your first booking!

Join misterb&b

There are many other sites for apartment rentals including Airbnb, Vrbo and Booking.com. All three companies have inclusive policies and support the LGBT+ community. Prices are generally comparable to budget hotels, especially if you’re willing to get a room in a shared apartment. Book VRBO →

Featured Image credit: Island House Key West