Gay Key West · Hotels

Alexander’s Guesthouse is a gay-only resort in Key West close to the gay nightlife of Duval Street. This guesthouse is a stylish restored conch house, originally built in 1902.

It’s located in Key West Old Town on a quiet street. Comprised of three renovated buildings, there are seventeen rooms available. Due to its historical significance, Alexander’s is registered with the Key West Historical Society. The rooms are a charming blend of old school and modern style.

Poolside happy hour takes place between 16:30 – 17:30 and you can take a dip in the jacuzzi when the mood takes you.

When you’re ready to party the gay nightlife is just moments away.

The Island House, a clothing-optional gay resort in Key West. It’s just 6 blocks away from the nightlife of Duval Street.

You can relax any time of day or night in the largest guesthouse pool on the island, which is heated in the winter. The poolside cafe and bar serves drinks, meals and snacks all day and all night, every day. There’s plenty of deck space around the pool for sunbathing, as well as a private sundeck overlooking the pool with a misting system to ensure cool comfort in any weather.

Clothing is optional everywhere on the property except the gym. You can warm up in the indoor or outdoor Jacuzzi, dry sauna and steam room, or make a little heat of your own in the 24 hour erotic video lounge.

Island House is truly what you make of it, from quietly reading a book on the sundeck, to partying with new friends at happy hour in the pool. They truly provide the lush tropical setting that customers love, and you make the real magic happen.

The Silver Palms Inn has been one of the hosts for the popular Womensfest for years, and will be hosting again in September 2022.

Just a short walk away from Duval Street, Silver Palms Inn lies in the heart of the Key West Historic District. Choose between a room with pool or city view, or a suite that is overlooking the island. All rooms are air-conditioned and come with a flat-screen TV, iPod dock and a fridge. Continental breakfast and secured parking are complimentary.

Silver Palms Inn’s tropical island-themed decor is rounded with the outdoor saltwater pool that offers guests a cooldown from the Floridian sun. Ready for the night? Duval Street and most of its gay bars and clubs are a short walk from this hotel.

Located in the heart of the Key West Historic District, this colorful adults-only B&B has 10 modern rooms and a secluded outdoor pool where guests can relax and hang out in the heat of the Florida sun.

Housed in a Victorian building from the 1890s, all rooms are air-conditioned, have a TV, wireless charger docking stations, a microwave, fridge and coffee maker. The en suite bathroom comes with bathrobes and slippers. Some rooms also have sitting areas and French doors that open into a communal veranda with cute basket chairs.

Guests can enjoy the complimentary continental breakfast in the quaint first floor dining area.

The Ernest Hemingway Home and Museum is just a short walk away, as well as the charming boutiques and galleries along Duval Street. As the sun goes down, the gay nightlife centered around Duval Street comes alive – Bourbon Street Pub and 801 Bourbon Bar are less than a 10-minute walk from La Pensione Inn! 

The Casa Marina Hotel Key West is a Whaldorf Astoria Resort. It was built in the 1920s and sits on 1,100 feet (1/4 mile) of private beach featuring two large oceanfront pools. The grand staircases and wooden beamed ceiling, provides a vintage Key West flair.

There are many activities that would be available to you as a guest, such as sunset cruises. Deep sea fishing and various water sports too.

The hotel is located on the outskirts of Old Town, which provides more seclusion without being far from the hustle and bustle. Nearby attractions include; Edward B. Knight Pier, The Hemingway Home Museum and The Higgs Dog Park (all under a 15-minute walk away).

The various food options include the hotel’s restaurant, the Flaglers Ballroom. Alternatively, both budget and upscale options are within a 15-minute walk.

After your meal, there is the choice of exploring the local nightlife. Bourbon Street Pub and One Saloon are very popular gay bars, only 20-minutes away by foot.

The Gates Hotel bordering the Salt Pond Keys offers stylish modern rooms. You even get a welcome cocktail on your way in.

The rooms come with hardwood floors, free Wi-Fi, coffee makers, mini-fridges and high-end toiletries.

If you enjoy a smoke make the most of the cigar bar. You’ll no doubt wish to savour one with a choice selection of rums.

There’s a year round outdoor pool and frequent live music event.

When you’re ready to explore the island a free shuttle bus awaits you.

Popular Key West LGBT hotel La Te Da, is located on Duval Street.

This chic, modern hotel maintains its old-world, quintessentially Key West style. As well as nicely appointed guestrooms the hotel offers regular cabaret entertainment at The Piano Bar from local and visiting drag performers. Head to the open air Terrace Bar to have a civilized drink and watch the world go by. The restaurant serves a wide selection of American and European food.

You’ll have free access to the outdoor pool.

Each room has its own unique style so see which one takes your fancy before you book.

When you’re ready to party the nightlife of Duval Street awaits you.

This iconic hotel is situated on Duval Street near the gay nightlife. La Concha is something of an institution.

The famous property is a National Historical Landmark. Built in 1927, it has hosted Harry Truman and the authors Ernest Hemingway and Tennessee Williams – both of whom wrote some of their famous works here. This will no doubt motivate you to visit the nearby Ernest Hemingway Museum.

The chic, modern rooms come with free Wi-Fi and flat screen TVs.

The hotel’s rooftop bar is a famous Key West spot where you can enjoy cocktails and watch the sun set over Key West.

You can also make use of the fitness centre, pool and seafood restaurant.

When you’re ready to party the celebrated gay nightlife is on your doorstep.

Kimpton Ridley House (formerly Cypress House), a boutique hotel, is close to the Key West’s gay nightlife on Duval Street. Nearby attractions include Mallory Square, for the nightly sunset celebration. The hotel is located close to the hustle and bustle, whilst still being secluded and private.

It is a historical landmark, with the 19th-century building is designed in a classic colonial style. The adults only hotel combines its classic aesthetic with modern decor. Be sure to enjoy the 40 foot heated lap pool in the hotel’s private garden.

Breakfast is included and served between 08:00 – 10:00.

The Equator Resort, Key West’s male-only, clothing optional resort. Comprised of 5 historic properties, all rooms in the resort are unique and have their own private bathroom. Some rooms have special luxuries like wet bars, skylights, and two-man whirlpool bathtubs.  Guest privacy is a top priority and the resort does not offer day passes and is guests, and guests of guests exclusive.

The Equator Resort offers a large, lush, and open private setting with 2 heated pools and two hot tubs. The resort also features complimentary breakfast and happy hour daily, as well as a full-service bar. On-site massage is available, along with complimentary weekly morning poolside yoga, sleeping masks, Direct Tv, 11 Male Only Adult Channels all located in a quiet residential area, but still only 3 blocks from World Famous Duval St.

Located in Downtown Key West in the heart of the gay nightlife, Pegasus International Hotel offers great value for money. The chic guest rooms and spacious suites are newly renovated. They come with microwaves, refrigerators and comfortable bedding.

Breakfast is included as well as free Wi-Fi. For $15 a day you have access to parking.

There’s a poolside bar, swimming pool and Jacuzzi.

When you’re ready to party the buzzing nightlife of Duval Street is right on your doorstep.

This affordable hotel is located on Duval Street near to the gay nightlife and the Hemingway Museum. The excellent location makes walking easy.

The rooms are quaint and well-kept. Reviewers have noted the helpful staff and charming old school ambience.

A complimentary breakfast is provided each morning. The rooms come with a flat screen TV, private balcony and free Wi-Fi.

You can make use of the outdoor pool and sun-deck.

When you’re ready to explore the island all the action is right on your doorstep.

New Orleans House is a male-only, clothing-optional, guesthouse located on Duval Street.

The hotel features a clothing-optional pool, a sun deck, a garden bar area, and a hot tub too. The garden bar area is open all day until the early hours of the morning.

The New Orleans house is part of the Bourbon Street Pub complex which allows guests perks such as free entry and access to the pub as well as the drag shows.

This Marriott Beachside Hotel is situated on a seven-acre waterfront property boasting six three-story buildings, and even a helicopter pad. So this place is a must if you have a helicopter.

If you don’t you’ll no doubt succumb to many of its other winning attributes. The chic and spacious rooms have a contemporary style, marble baths, iPod docks, flat screen TVs and sumptuous mattresses and sheets.

There’s a private sandy beach and a pool with a poolside bar and views of the Gulf Of Mexico. If you’re peckish you can head to the steakhouse.

You may want to get pumped at the fitness center before taking a free shuttle bus to Duval Street and partying the night away.

This stylish and quirky hotel is close to many of the main attractions, including the buzzing gay scene. It’s also offers easy access to the Duval Street shopping area, as well as cultural attractions like the Ernest Hemingway Home And Museum.

Free Wi-Fi and a complimentary breakfast are available. You’ll also have full access to the outdoor pool and the gym.

The decor may be slightly dated but the Fairfield Inn is immaculately clean, well reviewed and affordable.

The rooms have microwaves, mini-fridges and coffee makers, so you can eat in and save your money. If you intend to dine out there are many places to chose form in close range.