10 best gay resorts and gay hotels in Key West

Stefan Arestis

Key West is super gay! This small island in south Florida is a notorious gay mecca, with a whopping 30% of its 25,000 residents identifying as LGBTQ. 

The island's history as a gay destination dates back to the 1950s when well-known LGBTQ celebrities like Tennessee Williams, Gore Vidal, Truman Capote, Jerry Herman, Leonard Bernstein and Elizabeth Bishop have since made it their home. Subsequently in 1983, Key West became the first place in the US to elect an openly gay mayor (Richard A. Heyman), then in 2000, the island's motto became: One Human Family“.

We've visited Key West on several occasions and always had a blast, especially on the gay scene on Duval Street. There are so many things to do for gay travellers and with regards to to the hotels, it was never a case of ‘please can we have a double bed', but more – ‘which of these many gay hotels should we stay at on this trip?'

There are an impressive number of different gay resorts in Key West to pick from, so we've put together our 10 favourite, which also includes gay hotels and guesthouses. 

Enjoying the gay clothing optional hotels of Key West
Discovering the best gay hotels of Key West

1. Island House: men-only + clothing-optional 

Island House is infamous across the entire LGBTQ community of south Florida. It's one of the largest male-only clothing-optional resorts we've ever been to. Whether you come here to enjoy the facilities on a Day Pass or stay overnight, Island House is a gay man's paradise! They have clothing optional pool parties every Wednesday between 5-8pm and on Sundays from 12-4pm.

Facilities: there is a large outdoor Jacuzzi and heated pool with side bar, both open 24 hours a day. Happy Hour takes place between 5-6:30pm where free drinks are available for guests. Upstairs overlooking the pool is a large sundeck area. Indoor facilities include a gym, steam room, sauna and another Jacuzzi, all of which are available to use at any time. 

The rooms: Island House has a variety of basic rooms, some with private bathroom, others shared. In addition, they have more lavish suites and apartments to rent with a group of friends. If you don't want to stay the night, you can come to one of the pool parties or purchase a Day Pass to use the facilities.

Our opinion: this is an exciting gay man's haven! The crowd is on the older side, mainly in their late 30s and older. As stated above, if you don't want to stay here, you can instead just buy a Day Pass and come to enjoy the facilities.

Where is it located: 1129 Fleming Street, which is around 10 minutes walk from the gay scene on Duval Street.

Cost and how to book: rooms start from $200 for a basic room going up to $450 for a luxury 2 bedroom apartment. Booking is exclusive and only possible by contacting them directly.

2. Alexander's Guesthouse: LGBTQ mixed + clothing-optional

Alexander's Guesthouse is a clothing-optional gay guesthouse in Key West open to all sexual persuasions, with a mix of gay men and women. It's full of character, set in a restored 3-story Conch house built in 1902. A Conch house is a typical Key West house dating back to the 1800s, which is made from wood, set on posts, which allows air to circulate under the floor. The style was developed by immigrants from the Bahamas who were referred to as “Conchs”, hence the name.

Facilities: Alexander's has large bedrooms with king sized beds and private balcony. Communal areas include several sunning decks, a pool and Jacuzzi. Some of the communal spaces are clothing optional. They also have a cocktail happy hour at their aptly named in house bar: the Pink Monkey Bar. If coming with a group of friends you can rent out one of their larger apartments to share.

Our opinion: what makes Alexander's unique is that there is a mix of both men and women, which makes it feel less cruisy. Handy tip: try to book room #14 which has the Jacuzzi right outside.

Where is it located: 1118 Fleming Street, just down the road from Island House, and 10 minutes walk to the gay bars on Duval Street.

Cost and details for booking: rooms start from around $330. Note: they have a 2 night minimum stay requirement.

 

3. New Orleans House: male-only + clothing optional

This is in fact part of the Bourbon Street Complex, which has gay parties going on until 4am. It is the only male-only clothing optional resort in downtown Key West, directly on Duval Street.

Facilities: The rooms are located upstairs in the Bourbon Street Complex, directly above the bars/clubs, so it's very noisy! The rooms are not the most luxurious, but you have access to the facilities of the Bourbon Street Complex, which includes a 15-man Jacuzzi and a clothing optional private sun deck area.

Our opinion: if you've come to Key West to party till the early hours and want to be based right in the heart of the gay scene, then this is the best place to stay. However, if you just want to chill and relax, then avoid staying here as the parties downstairs go on until 4am. As a result of the high noise levels, the New Orleans House is a cheaper option compared to the other gay resorts of Key West. 

Where is it located: 724 Duval Street, right in the heart of the island's gay scene!

Cost and details for booking: rooms start from $175.

The New Orleans gay resort in Key West
The New Orleans House standing loud and proud on Duval Street!

4. Equator Resort Key West: male-only + clothing optional

Equator is another male-only clothing optional resort in Key West based on Fleming Street. It's smaller and more personable than Island House with a wide mix of rooms ranging from standard queens to larger apartment-style suites.

Facilities: there is a ground floor pool with sunken Jacuzzi, small bar and an area for sun lounging. Upstairs there is a larger sundeck area, which we found to be more private and better for nude sunbathing. They have a happy hour every day, which is perfect to socialise with other guests and make new friends.

Our opinion: If you want to stay in an exclusively gay, clothing optional resort, but not as large and overwhelming as Island House, then this is the place for you. Also, if you want more privacy, we recommend asking for a room near the front of the building, away from the pool area. If, however you're a social butterfly, and want to be at the heart of all the action, book one of rooms near the pool or on the upper-level sundeck.

Where is it located: 818 Fleming Street, just 3 blocks away from the gay scene on Duval Street.

Cost and details for booking: Rooms start from around $230 a night but booking is for a 3-night minimum stay. Online booking is not possible so you have to contact the Equator Resort directly.

5. La Te Da Hotel: mixed + adults-only

La Te Da is a large gay friendly venue with an excellent restaurant, Cabaret theatre and several rooms to rent. Although it's not clothing optional, it is exclusively for adults. It is particularly popular with gay couples. It's well located on Duval Street, just down the road from the main gay hangouts.

Facilities: there are 15 rooms at La Te Da. The more high end rooms feature marble baths, vaulted ceilings and hardwood flooring. The communal area includes a large pool and sundeck area. On Sundays they have a gay tea dance party in the afternoon, which is a fun alternative to the more boisterous pool party at Island Gardens. La Te Da also has a cabaret theatre with some of the best shows we've seen, in particular Randy Roberts.

Our opinion: we love La Te Da because it's ideal for couples, no screaming loud children and minus the cruisy atmosphere you tend to get from the male-only resorts. The restaurant/bar is a popular gay hangout, part of the Key West gay scene. Look out for the very charismatic and hilarious owner Chef Christopher, who may even let you touch his crown!

Where is it located: 1125 Duval Street, just minutes walk away from the gay bars of Key West.

Cost and details for booking: Rooms start from around $290 a night, but they have a 2 night minimum stay requirement.

Owner of La Te Da gay hotel in Key West
Hanging out with the very charismatic Christopher: chef and owner of La Te Da

6. The Gardens Hotel: mixed + adults-only

The Gardens Hotel is a super classy, 4 star hotel, famous for its wine collection. It was named “The Prettiest Hotel in Key West” by The New York Time’s List.

It has the perfect location, just minutes walking distance from the main gay bars on Duval Street. Although the crowd is mixed, we felt extremely welcome here as a gay couple. 

Facilities: rooms are spacious and really beautifully decorated. All rooms have a shared balcony or patio. The hotel has its own private parking area for guests, which is very handy! The buffet breakfast here is excellent – one of the best we've had from all our hotel stays in Florida. There is an outdoor pool area with bar, surrounded with lush gardens. On Sunday evenings they have a live jazz performing.

The main highlight of The Gardens Hotel is the wine gallery. They have a smart card system for wine tasting so you can do it yourself at any time of the day, or, join one of their wine tasting evenings.

Our opinion: this is perfect for gay couples who want to be located in the heart of the gay scene, but unlike at the New Orleans House, want to get a good night's sleep.

Where is it located: 526 Angela Street, which is minutes walking distance from the gay bars on Duval Street.

Cost and details for booking: rooms at The Gardens Hotel start from $410.

 

7. Cypress House Hotel: mixed + adults-only

Cypress is a gay friendly, adults-only, 3 star hotel, located a few blocks from Duval Street. The majority of the staff are gay (and super cute!) The building is full of character, set in an historic 1890s conch mansion.

Facilities: there are only 22 ensuite guest rooms at Cypress, some of which have private balconies or access to decks/common balconies. The common areas of the hotel include a large outdoor lap pool, landscaped sun lounging area and kitchen area where the breakfast is served. They also offer bike rentals for guests.

Our opinion: Cypress House Hotel is well known for being a gay friendly hotel in Key West. The majority of the staff are gay and obviously have no problems allowing 2 same-sex couples to share a bed. We love that it's set in a charming historical conch-style building, which gives it so much character. Also, the fact that there are only 22 rooms available means it's more personable compared to some of the larger commercial chain hotels.

Where is it located: 601 Caroline Street, close to Mallory Square and around 10 minutes walking distance to the gay bars.

Cost and details for booking: rooms start from $375.

Relaxing at the swimming pool of the Cypress House Hotel
Chillin' by the pool in Key West in our star-spangled swimsuits!

8. Southernmost Beach Resort: mixed + adults only

The Southernmost Beach Resort is one of the most luxurious and stunning hotels we found in Key West. It's huge, set over 6 acres of land, located right by the beach. It is so beautiful that it's become a popular location for weddings.

Facilities: the resort is set in two historic buildings, with no fewer than 261 elegantly furnished rooms reserved exclusively for adults. The rooms are decorated in a very modern style, spacious, with plenty of storage room. They have 3 pools, 4 tropical bars, plenty of greenery and oceanside hammocks to relax in.

Our opinion: this is one for couples looking to celebrate a special occasion. Visually it was our favourite gay hotel in Key West and one we'd recommend to couples looking to splash out. The best rooms are those overlooking the Atlantic Ocean.

Where is it located: 1319 Duval Street, close to the Southernmost statue, round the corner from La Te Da and around 10 minutes walk to the gay bars.

Cost and details for booking: rooms at the Southernmost Beach Resort start from $250.

 

9. Simonton Court Historic Inn & Cottages: mixed + adults only

Simonton is a gay friendly adults-only 4* hotel set in a large 2 acre compound. The compound includes historic cottages, a Victorian mansion, a townhouse and a 1880s cigar factory. The cigar factory has been converted into a hotel where you can book a room to stay in. Alternatively you can book one of the cottages, which is where the cigar factory workers used to lived.

Facilities: rooms are spacious, decorated with much of the original features in place. The beds are extremely comfortable. Simonton has 4 pools and a pretty brick courtyard area where breakfast is served.

Our opinion: larger resort than the Southernmost Beach Resort and full of charming history dating back to the late 19th century when the cigar industry was booming in Key West. It's an ideal option for couples looking for a serene and peaceful stay in Key West.

Where is it located: 320 Simonton Street, just a block away from Duval Street and 3 blocks from the vibrant Mallory Square. The gay bars are around 10 minutes walking distance.

Cost and details for booking: rooms start from $375.

 

10. NYAH Not Your Average Hostel: budget + adults-only

Yes Key West is very expensive. Many locals will have at least 2/3 jobs to make ends meet. As such, accommodation options are not the most affordable. Even for a basic guesthouse or Airbnb in Key West, you need to budget for a few hundred dollars a night. Having said that, we discovered a gay friendly hostel in Key West called NYAH, which is ideal for solo gay travellers on a budget.

Facilities: the NYAH has 36 rooms, each sleeping 4-6 people. They have all-female dorms as well. In terms of the communal areas, they have 3 pools and 2 Jacuzzis.

Our opinion: personally, as a gay couple travelling to Key West, we prefer to splash out a bit and book our own little private love nest. However, for solo gay travellers on a budget, who don't mind sleeping in a dorm, this is ideal.

Where is it located: 420 Margaret Street, which is around 10-15 minutes walk to the gay scene on Duval Street.

Cost and details for booking: beds at the NYAH start from $100 a night.

STAY WITH A GAY LOCAL

Misterb&b is the Airbnb equivalent for the LGBTQ community. Unlike on Airbnb, you know your host is gay, avoiding any nasty surprises when you check in. It is also a great way to meet gay locals and discover the underground gay scene. Click below to get 10 € (or $10) off your first booking.

Happy travels are safe travels

We recommend you always take out travel insurance before your next vacation. What happens if you suffer from illness, injury, theft or a cancellation? With travel insurance, you can have peace of mind and not worry. We love World Nomads travel insurance and have been using it for years. Their comprehensive coverage is second to none and their online claims process is very user friendly.

Some of the links in this post are affiliate links. This means that if you book your accommodation, an activity or your insurance, we’ll earn a small commission. There is never an extra cost to you for using these links and it helps us keep the site going.

For more inspiration check out our gay guide to Florida Keys and more gems from big road trip in Florida:

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10 best gay hotels and resorts in Key West
Stefan Arestis

Stefan is the co-founder, editor and author the gay travel blog nomadicboys.com. As a travel nerd, he has explored more than 80 countries across 5 continents. What he loves the most about travelling is discovering the local gay scene, making new friends and learning new cultures. His advice about LGBTQ travel has been featured in Gay Times, Gaycities, Pink News, Gay Star News, Attitude and Towleroad. He has also written about gay travel for other non-gay specific publications including Lonely Planet, The New York Times, The Guardian and The Huffington Post. Stefan is also a qualified lawyer, having practised as a commercial property litigator in London for over 10 years. He left his lawyer days behind to work full time on Nomadic Boys with his husband Sebastien. Find out more about Nomadic Boys.

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