Queer inclusiveness is steeped deep into the fabric of Key West, the notorious gay island mecca in South Florida. As a place with a 30% LGBTQ population, Key West has always attracted gay travelers. So, we found ourselves drawn to this coastal mecca, the heart of whose gay scene is Duval Street. Not only does it house some of the best gay hotels in Key West, but it’s also home to some amazing gay bars. In fact, Duval Street is also where we found some of the best swankiest LGBTQ-friendly Key West resorts. So, we had so many options that we found it hard to choose a place to stay. Luckily, we sorted the hotels on the basis of budget, amenities, their proximity to Duval Street and other Key West sights, and even the friendliness of the staff – and came up with this list for you.
Key West’s reputation as an LGBTQ refuge goes back to the ’80s when the city was one of the first cities in America to elect an openly gay mayor. Ultimately, the island saw many gay and lesbian travelers become permanent residents, and even today, it remains a popular LGBTQ+ spring break getaway. Apart from Key West Pride, we also got to experience the hot-hot Tropical Heat party. There’s also the 10-day extravaganza Fantasy Fest and the Key West Bear Weekend. Since we were looking for a laid-back holiday on the island, we were able to enjoy the island’s white-sand beaches too. Of them all, Higg’s Beach happens to be Key West’s unofficial gay beach. All in all, these digs surely made our sun-sand-and-sea Floridian gay-cation a lovely one!
Table of contents
Island House
11
Best exclusively gay resort. Island House is one of the best gay Key West resorts, as well as one of the world’s best gay resorts. It’s famous across South Florida’s LGBTQ community for being the largest male-only, clothing-optional gay hotel in Key West. Their free happy hour usually makes it very relaxed to introduce oneself to everyone else. That, along with the fact that it’s chock-full of social amenities, had us excited to stay here.
Think this – a sauna, a steam room, a five-man shower, a Jacuzzi, a pool, a sundeck, a bar, and even a darkroom, which we were feeling particularly adventurous towards! With day passes available to non-guests, Island House is one of Key West’s top destinations for cruising and socializing. In fact, we even attended the very popular clothing-optional happy hour pool party every day between 5 and 6:30 pm. Since we were staying here, we got four complimentary cocktails! Even for day guests, the Happy Hour here had 50% off of everything at the bar. It’s no wonder that this is a very popular place to be on the island. We loved the late-30s-and-older crowd, making this a gay man’s heaven. Even then, the exciting gay nightlife of Key West is a mere 15-minute walk.
The rooms at Island House range from basic ones to lavish suites and apartments for group revelries. Since we were in a group, we chose the two-bedroom Arch House, which even came with a separate kitchen to cook meals. Notwithstanding the room, the TV channels play gay videos and movies as well.
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Alexander’s Guesthouse
10
Best adults-only. It’s in the name – Alexander’s Gay Lesbian Guesthouse is the only gay Key West resort catering to a true mix of men and women. The demographic at this adults-only resort made the atmosphere feel a lot less cruisey and a lot more charming and interesting. The clothing-optional gay Key West hotel/guesthouse is set up in a restored 19th-century, three-story Conch house typical of Key West. While all the spacious rooms have their own balconies, we opted for the Deluxe Suite, which comes with its own private sundeck.
We especially loved the communal areas here, which include the Jacuzzi and the pool. The highlight is the several sundecks (some clothing-optional), all of which are great for lounging and meeting new people. Moreover, the lending library appealed immensely to the bibliophiles amongst us, who curled up with books on the cushy sofas. Come evening; we’d be pre-boozing at the cocktail happy hour at the in-house Pink Monkey Bar before heading out to Duval Street’s fabulous gay scene 10 minutes away.
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New Orleans House
9
Best hotel for parties. Gay-friendly? Check. Only males? Check. Adults-only? Triple check! We wanted to party till late in Key West while being budget-savvy and chanced upon the New Orleans House. The guesthouse is part of the Bourbon Street Complex, where we saw gay parties go on until 4 in the morning! It’s also the only gay Key West resort downtown that’s only male and clothing-optional, too – so we knew we had to stay here.
While the rooms weren’t the most luxurious and see noise from the Bourbon Street Pub downstairs, the place is cheap and perfect for us party-loving revelers. What’s more, we even had access to the clothing-optional private sundeck area, the amazing pool, and the bar. The best bit? There was a huge Jacuzzi in the complex, too, and it could accommodate 15 men at a time. Party indeed!
Since New Orleans sits right in the middle of Duval Street’s action, we ended most of our nights downstairs at the Bourbon Street Pub. The gay paradise of a bar has a dancing area, a pool bar area, and sexy topless staff. That’s why it also happens to be one of the best cheap hotels in Key West, FL.
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Kimpton Ridley House
8
Most romantic. The adults-only, gay-friendly Kimpton Ridley House was the perfect base for us to combine our gay and sea adventures. This Key West hotel is just a few blocks from Duval Street as well as the Key West waterfront. So, we were close to where most of the island and sea adventure tours took off. We indulged in the Sandbar Excursion & Kayak Tour, which not only took us to some of the world’s clearest waters, but that took with lunch and drinks. The best bit is that Duval Street and its gay offerings are just a 10-minute walk away.
Back at the guesthouse, the digs are set in a charming 19th-century Conch mansion – but we especially loved the super-cute gay staff. We had the choice of just 23 rooms, which meant that staying here was a super-intimate affair. While all rooms are spacious with soft beds and amazing mod-cons, we loved the Essential King Room, which came with a large patio and alfresco furniture. It was the perfect place to begin our days with coffee. But the common areas are particularly fantastic, like the communal kitchen. But the best of the lot is the landscaped sun lounging area, in the middle of which sits the most inviting-looking outdoor lap pool we’ve ever seen.
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The Gardens Hotel
7
Most luxurious. How would you like to stay in what was once Key West’s largest private estate? We had the same thought! Welcome to The Gardens Hotel, which was undoubtedly the most luxurious hotel on the entire island. We felt like royalty the minute we stepped into this super classy, four-star hotel that’s famous for its wine collection. It’s surrounded entirely by lush gardens and was hailed as the “The Prettiest Hotel in Key West” by The New York Times – and we couldn’t agree more. It’s also one of the best boutique hotels in Key West. Plus, it’s just around the corner from Duval Street, so what could be better?
What we liked is that all rooms have a shared balcony or patio. But we felt like royalty in our elegant, tropical, and spacious Master suite. With original artwork, hand-carved plantation-style furniture, and a plush four-poster king bed, the vibe was thoroughly Key West. Mod-cons like a fridge, a Keurig coffeemaker, and a flat-screen TV make it all the better. And, of course, there was the private verandah with stylish loungers that overlook the gardens.
We especially appreciated the hotel’s private parking area for guests. We were welcomed with champagne, and we booked our specialty package, which included a romantic dinner in the gazebo. Bikes for rent aside, the hotel arranged for massages in our room. The star attraction is the freeform pool with modern loungers and lush foliage.
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The Mermaid & The Alligator
6
We were looking for an elegant gay stay in town, and we found the adults-only Mermaid & The Alligator to be one of the classiest gay hotels in Key West. The sophisticated, whimsically-named LGBTQ-friendly property sits in a 19th-century Queen Anne mansion with picture-perfect landscaped gardens. The rooms ranged from classic ones to a treetop suite. We chose the Caribbean Queen room, a gorgeous and spacious room with a bathtub for two in the bathroom. Not just that, but it also has a patio terrace with alfresco furniture and a hammock and offers lush garden views.
The rest of the hotel was equally amazing, with a ton of communal amenities. Our days began with a complimentary breakfast, after which we’d spend time in the common lounge with games and a TV. But most of the time, we’d spend in and by the heated pool on the sun terrace. Since it had superb concierge and poolside service, all we had to do was simply wish for it – and the staff would provide it. Staying at the Mermaid & the Alligator was also great for soaking up some local history and culture. That’s why we indulged in this wonderful 3-hour Southernmost Food and Cultural Walking Tour, which began just five minutes away from the hotel.
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Nyah, Key West
5
It’s all in the name of the adults-only, gay-friendly Nyah. Managed by Not Your Average Hotel, this place features a unique “Build your own room concept” for up to six guests in one room and even has single travelers’ rooms. Since we were on a mancation here, we configured the rooms according to our needs and chose bunk beds for six. What’s more, every bed had its own RFID locking closet and a charging station/lighted nook. The best bit? We even got a flat-screen TV and a mini fridge for spending a humid afternoon in with chilled beers.
The rest of the beautifully modern not-a-hotel features a smattering of amenities that are pampering to the hilt. We loved the option of the three pools, two jacuzzis, and the multiple sun decks – yeah, plural! What’s more, our days began with a delectable continental breakfast spread at the poolside. And, of course, the lobby bar had happy hours in the evening, after which we’d step out to explore the city’s gay scene. Since Nyah is located right in the heart of town, the gay bars of Key West on Duval Street are a stone’s throw.
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Hyatt Centric Key West Resort and Spa
4
If you wish to splurge on out-and-out Florida Keys luxury, the waterfront Hyatt Centric Resort and Spa is one of the best gay friendly hotels in Key West . Housed in a beautiful Caribbean colonial-style structure, the boutique Hyatt Key West was neither a cookie-cutter chain property nor was it overwhelming. We were impressed by the spacious rooms, all of which come with balconies with lovely Gulf of Mexico views. The King Salon room, where we were staying, came with a separate living area with superb views of the hotel and the Gulf of Mexico. Moreover, mod-cons made our stay as comfortable as it could get.
However, it’s the splendid amenities at the property that we were blown away by. After a long day of exploring Key West, we headed to the spa Jala, which is the property’s highlight. Indulging in a soothing couple’s massage was the best thing we did all day, besides swimming in and lounging by the large heated pool, of course.
Last but not least, Hyatt’s proximity to both the gay scene and the Key West Harbor made it the perfect base for partying the night away and indulging in water activities and trips.
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Southernmost Beach Resort
3
Best heritage hotel. The Southernmost Beach Resort lies right next to the historic landmark that is the southernmost point in the continental US. One of Key West’s most luxurious gay hotels, the resort is also the southernmost LGBTQ+ hotel in the US. Since it’s near Duval Street and overlooks the ocean, it was perfect for our well-rounded Key West holiday.
What’s more, it’s huge, so much so that we had the choice of more than 250 spacious and modern rooms across several historic structures. We fell in love with the La Mer and Dewey Ocean View room, whose balcony/patio leads directly to the sandy beach. With mod-cons like coffee/tea-makers, flat-screen TV, blackout curtains, and a luxe bathroom with bathrobes and a bathtub, staying here was a dream.
“Key West’s tropical vibe, along with its heritage elements as well as modern ones – we couldn’t reallt ask for anything else at this amazing beach resort.”
WOW Travel
The amenities at this resort were top-notch. For one, the hotel has four tropical bars, oceanside hammocks, and sun loungers that sit right in the water. So, it made for the most romantic of settings for us and our partners. Of course, there are three ocean-facing pools to choose from, depending on the vibe we were in the mood for. The highlight was the couples’ massages we got in the massage cabanas that overlook the Gulf of Mexico.
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La Te Da
2
The adult-only La Te Da is more of a large gay-friendly venue rather than just a hotel. Not only does it have luxurious rooms, but it even has a restaurant and one of the most popular Cabaret theaters in the Keys! That’s what drew us to this place, besides the fact that it sits just down from popular gay bars in Key West. The rooms ranged from compact to high-end ones. Even the most economical rooms feature private baths, and we chose the Deluxe poolside rooms. So, the minute we stepped out of our rooms, we were right by the pool!
But we were really here for the cabaret shows, which showed us a wild, adults-only glimpse of Key West’s naughtier side. Moreover, we loved the communal areas at La Te Da, including the large sundeck area and pool, where the legendary gay tea dance party takes place. Every Sunday afternoon, this longstanding party is extremely popular with gay locals and travelers, and we met a lot of interesting people. The cabaret theatre at the hotel has some of the best drag shows in Key West, and the bar restaurant is a very popular gay hangout. All these do make the area a bit crowded, but the mixed demographic makes the atmosphere a lot less cruisey.
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The Marker Waterfront Resort
1
Staying in the eclectic Key West style at the fabulous Marker Waterfront Resort right on the historic Key West harborfront was one of the best experiences. The location was fantastic for exploring the waters and sights of Key West. Plus, Duval Street’s gay scene was just 15 minutes away, making the Marker the perfect place to stay. All rooms at the Marker feature private balconies and are beautifully furnished to inspire romance. We ended up choosing the Harbor View King with Balcony, which was not only spacious but had a superb view of the harbor from the outdoor patio. A curated minibar, a coffeemaker, a soaking tub with bathrobes, and a plush bed made this room the highlight of our stay.
Downstairs, we had the choice of two superb saltwater pools to lounge at. But since we were on a romantic holiday, we loved the adult-only Serenity pool the most, complete with sun loungers. They even have a local-friendly policy, and we met some of the best people ever who told us a wealth of Key West stories. An open-air pool bar and a waterfront restaurant serve cocktails and drinks and all meals, appetizers, and small plates. It’s no wonder that it’s one of the best beachfront hotels in Key West.
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Our Verdict!
While all Key West LGBTQ hotels are amazing, the ones below are extra-special:
- Best exclusively gay resort: Island House
- Best adults-only: Alexander’s Guesthouse
- Best hotel for parties: New Orleans House
- Most romantic: Kimpton Ridley House
- Most luxurious: The Gardens Hotel
- Best heritage hotel: Southernmost Beach Resort
Just So You Know:
- Key West has the highest percentage of gay-friendly aquatic activities in America, maybe even the world. There are gay sailing charters, gay speedboat rentals, and so much more.
- In a town where 30% of the population identifies as LGBTQ+, be sure to talk to the locals. They will have tons of tales to tell you about the island’s gay history and other interesting info as well.
- Key West has tons of clothing-optional activities – snorkeling, beach-going, sailing, and nude pool parties. You can even lounge sans clothes on the sun decks in some gay-friendly hotels in Key West.
Get Some Culture in Key West:
- Key West Pride: Key West’s annual pride celebration is all about endless queer parties paying tribute to the philosophy of “One Human Family”.
- Fantasy Fest 2018: Key West’s biggest gay event rivals even the Rio Carnival and NOLA’s Mardi Gras in terms of pleasure and debauchery. This 10-day extravaganza features lots of alcohol, body painting, drag queen contests, parties, and a parade.
- Gay Spring Break Key West: Tons of sexy, hot men come to gay Key West for epic events, shows, adventures, and parties.
Best Gay Bars/Clubs in Key West:
- 801 Bourbon Bar: Located right next to the Rainbow Crosswalk on Duval Street, the 801 bar and club is a great place to down a few cocktails to begin the night. Parties go on till 4 am.
- Bourbon Street Pub: Featuring speedo-clad Bourbon Boys standing outside, this gay men’s paradise features a dance area, a pool bar, and sexy staff that takes your orders topless! This is one of the most notoriously fun-filled and cruisy gay bars in Key West’s Duval Street.
- Bobby’s Monkey Bar: This popular gay dive bar is a quintessential gay neighborhood bar. It’s popular with both men and women.
- Saloon 1: Featuring everyone from otters, bears, and leather daddies, this only-male leather bar is right in your face. Friday midnights are devoted to Cock Shock. Here, prizes are given out for best butt, best chest – well, you get the drift.
- Aqua Nightclub: Key West’s best nightclub with quirky themed events in the heart of Duval Street. Those up for dancing and partying all night, head here.
Best Gay Saunas in Key West:
Key West doesn’t specifically have saunas – rather locals and travelers head to raunchy clothing-optional gay Key West resorts with saunas. In Key West, such options currently include Island House and the New Orleans Guest House.