Our guests! Island House Key West has been called “The Best Gay Resort in the World” by a number of national and international publications, including OUT Traveler and The Travel Channel US and UK. But what makes Island House truly special are the amazing men that keep coming back year after year to spend their hard earned vacations with us. 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. We simply provide the lush tropical setting that we know and love, and you make the real magic happen.

Yes, we carry many items that are already gluten free. However, we suggest you let us know your gluten concerns when booking your vacation, so that we can make sure to have some extra options on hand, just for you.

Shy or not, you blend right in at Island House. No pressure. No judgements. This place is exactly what you make of it! However, many of our guests return year after year because of the ease of meeting new friends in a comfortable and relaxed environment. Not to mention, free happy hour usually makes it pretty easy to introduce yourself to fellow guests.

We use #IslandHouseKW consistently through our social media outlets. You can easily find us on Twitter (#IslandHouseKW) and Facebook (Island House Key West Gay Hotel & Resort), with an audience of over 150,000 fellow fans! You can also see some of our more risque pics on the Island House Key West Tumblr page.

Candid guest reviews can be found on TripAdvisor, as well access to a number of pics (both professional and contributed) of our resort.

Because our historic buildings are made of wood, and lack modern sprinkler systems, our insurance company requires us to prohibit smoking in all indoor areas of the hotel, including guest rooms. The State of Florida prohibits smoking in the Cafe and Bar areas. Smoking is currently permitted in our designated outdoor area on the 2nd floor sundeck.

Everyday between 5PM and 6:30PM, we transform from a relaxing poolside resort to fabulous big gay party!  The beats get faster, the volume goes up, and the free cocktails flow freely.  This daily happy hour party includes 4 complimentary cocktails for our in-house guests. Our Happy Hour menu includes many of our most famous cocktails and frozen drinks made with premium spirits brands like Stoli Vodkas, Fords Gin, Bacardi, Captain Morgan, Jack Daniels and Johnnie Walker.  Our bar exclusively carries call & premium brand spirits, craft beers, wine, and champagne.  For everyone else our Happy Hour is 50% off everything at the bar, which makes this daily event VERY popular and a great way to make new friends. 

Yes, we have a complimentary high-speed WiFi network which is accessible from your room as well as all around the resort.

You can relax any time of day or night in the largest guesthouse pool on the island, which is heated all year. Our 24hr 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 in the clothing optional side of the resort except the gym. You can warm up in our Jacuzzis, sauna and steam room anytime your heart desires. Our locker room and gym makes it easy to keep up your routine while you are with us, and is also open 24 hours a day.

Yes! You can disrobe as soon as you enter the front door and throughout our clothing optional side of the resort. Island House is what you make of it. Some of our guests love the freedom of being nude all the time, and others prefer to stay covered. Whatever makes you happy and comfortable is our only concern.  The one exception is the gym, where State Law requires shoes and shorts.

Imagine a five-star resort on a smaller scale, catering to the needs of gay, queer, bisexual and trans men. Island House offers amenities like feather-free luxury bedding, memory foam high end beds and free super fast WiFi. At Island House, over 47 guys take care of just 39 rooms. You’ll feel pampered by those who understand you the most. Island House offers complete resort facilities including a 24hr restaurant, bar, and health club. You’ll always be able to do what you want. When you want. Since 1976 the oldest operating gay men’s resort in the world.

An Island Mate is on duty in the lobby and the cafe 24hrs a day to protect the Island House experience. Our front desk requires all guests to be registered and personally “buzzes in” all visitors and guests through the one and only resort entrance and exit. We also believe that protecting this unique experience starts way before you arrive, which is why we insist on having personal contact with each guest during the booking process, and don’t accept anonymous online reservations from any websites, including our own. We are very fortunate that Key West is so accepting and loving towards the gay community, but just like anywhere else, common sense is key. If you notice anything you think we should be aware of, have no fear to simply let us know. Our goal is to ensure everyone has a comfortable and safe vacation, all while having a great time.

Island House is 100% committed to maintaining the highest privacy standards when it comes to protecting our guests. We understand how important confidentiality may be to some guests and take great lengths to protect your Island House experience and your privacy. We NEVER sell or share your information with anyone, and if you do not wish to receive any mail or email from us, simply notify the front desk and we will note your folio accordingly.

Key West has a year-round tourist season, and what month you choose to visit usually indicates what type of vibe you enjoy on vacation. The winter months are obviously the most in-demand with many seeking a warm place to vacation, but summer months and shoulder seasons feature some of the island’s most spectacular special events, and offer the same magical Island House experience. At Island House, some of the “slower” months on the island really don’t seem that way within the sanctuary of our resort.

Key West offers a number of gay activities to choose from, from clothing-optional snorkel trips, day drinking on a remote sandbar, sunset cruises, and seasonal gay trolly tours. Many restaurants and shops are within walking distance from the Island House, which have many offerings that are specific to gay men’s interests. And ofcourse, you will find additional gay specific activities during any of the island’s infamous annual gay events.

For all of your rental needs, simply ask our front desk TEAM to make the reservations for you. We’ve got quick local access to some of the most respected island outfitters, from bicycle delivery to & from the resort, scooter rentals, electric cars, as well as watersport adventures like jetskis, kayaks, and paddleboards.

Check out our Key West page for more details on our favorite places and call or stop by and speak with one of our Island House TEAM members, who double as Key West recommendation experts. We’ll suggest the ‘can’t miss’ hot spots and make reservations if you like. That said, don’t forget that the Island House Cafe is open 24hrs, and is comparable to some of the best the Key West offers. We have an impeccable reputation amongst locals and visitors alike for the quality, variety and consistency of our restaurant.

There are several public beaches within an easy 10 minute bike ride of Island House, and others that are a quick Taxi/Uber/Lyft. Check out our Key West page for more details and photos.

Key West has a number of iconic gay bars and very gay friendly watering holes. Check out our Key West page for more details and photos. Our most famous gay bars include Bourbon Street Pub, Aqua Nightclub, Back Bar, Side Bar, The 801 Bourbon Bar, Saloon1, Bobby’s Monkey Bar, and La-Te-Da. The vast majority of these places are all open until 4AM.  These bars offer among them a video bar, a dance bar, drag shows, a leather-levi bar, a local’s karaoke bar, a cabaret, and piano bar. Bourbon Street Pub has totally nude male dancers every night beginning at 10PM. La Te Da holds their world famous Tea Dance on Sundays beginning at 4PM (right after our Hot Naked Sunday Pool Party). Key West is quite possibly the most gay-friendly town you will find in the United States!

We could spend a lot of time on this topic! Check out our Key West page for lots of information and pics about the fabulous things to do on our tiny Island.  Key West has a lot to offer. Snorkeling, sailing, jetski tours, para-sailing, seaplane rides, tours and museums of all sorts, and of course a terrific nightlife! As well as a host of excellent restaurants, historic seaside bars, and wine spots, there are a number of hot gay bars to choose from. Once you are ready to make plans, give the front desk TEAM a call, as they are all Key West experts and can answer questions, make recommendations, and even book reservations for you!

Not much! Key West is a super-laid back town and casual dress is perfectly acceptable at all our restaurants and bars, even the really exceptional ones. Flip flops are perfectly acceptable in basically every venue. We provide free use of pool towels and custom made sarongs, as well as we sell suntan lotions, sarongs, T-shirts, and ball caps. In winter, although warm by day, we do suggest you bring a light jacket or long sleeve attire, as the temperature in the evening can very occasionally reach the 60’s. If you are interested in snorkeling or diving, all of the boats provide the appropriate equipment.

Of course! We carry a full selection of bottled wines and champagnes, and we can have your gift waiting in your room upon arrival. This can come with a personalized gift message on Island House stationary for no extra charge. Just give us a call, and we will connect you with someone from our Food & Beverage TEAM. We kindly ask for 24-hours notice for this service. For a menu of our available selections, CLICK HERE.

We highly recommend not bringing a vehicle as parking can be a challenge on a small island. Our luxury apartments offer a dedicated parking space on Stickney Lane for each unit. We also offer first-come-first-served complimentary parking on the Fleming Street side of the resort.
If parking on a city street, make sure you do not park in a spot painted “Residential Only,” unless you have local Key West parking permits.

You must cancel reservations 15 days prior to your arrival date in order to receive a refund of your deposit. Cancellations MUST be made via phone calls. All cancellations will be charged a $50 administrative fee.  Cancellations within 15 days forfeits the entire deposit.  Deposits for certain holidays and Fantasy Fest are subject to special refund policies which will be explained to you when you make your reservation.

An email confirmation will be sent to you upon payment of the advance deposit on your reservation. We respect everyone’s privacy, so if you do not wish to receive correspondence from us either electronically or in the mail, please notify the front desk TEAM upon booking.

An advance deposit is required to confirm a reservation. We accept VISA, Mastercard, American Express, Discover, money orders, travelers checks and cash. Personal checks are not accepted. All reservations require a 50% deposit upon booking. The balance of the room charges and taxes is charged upon check in.

All rates quoted are for one or two people sharing the same room. Additional guests may be registered at a charge of $50 per night, per extra person. A maximum of two people per bed are permitted to register per room. If you bring a friend to your room for the day, please make sure to register them at the front desk for security reasons. All guests must be registered.

Yes, there is a three night minimum stay on weekends.  That said, certain busy periods like holiday and event weekends, Fantasy Fest and New Year’s are subject to longer minimum stays. In such cases, there will be no refunds for stays that are shortened to fewer days than the minimum stay required.

We ask that guests give us 24 hours notice of their intention to depart earlier than their scheduled date. 

All of our current published room rates can be found under each room type on our ROOMS page.  These rates are subject to change without notice, but all confirmed reservations with deposits will be honored regardless of any rate changes.  These rates do not include State and County Sales Taxes of 12.5%

We are on the gay “Guesthouse Row” in Old Town, at the end of Fleming Street. This is six blocks from Duval Street, or about a twelve minute walk at an easy pace. Specifically, we are at the corner of White Street and Fleming Street. Click here for Google Maps.

Check out is at 11AM. If you are leaving later in the day, we can store your luggage and you’re welcome to enjoy the facilities until it’s time to head home. If someone is not checking in, it is also possible to rent your room until 4:00pm for a half day charge. 

We always do our best to accommodate early arrivals. We have a 24 hour front desk TEAM, so there is always someone to greet you when you arrive. If your room is ready, you may certainly check in when you arrive, assuming it is the date of your reservation. (Our day starts at 8AM) If your room is not ready, we can store your luggage and you are welcome to enjoy the facilities while we prepare your room.

Yes! We have a 24 hour front desk TEAM to handle the latest of arrivals. And since late arrivals will sadly miss our free happy hour, you will receive a free cocktail coupon upon check-in to help get you settled. 

The simple answer is YES. As much as this may be a shock to many folks, Island House has rented rooms to women as far back as the early 2000’s when the resort acquired the additional detached units across Stickney Lane. These beautiful apartments have always been welcome to non-male guests because they are not located or have access to the clothing optional compound of the resort. To protect our male guest’s right to privacy when nude, non-males are not allowed on the clothing optional side. That said we do offer an auxiliary cafe area by those apartments where all food and beverage may be ordered and served as well as 24/7 room service, access to the Alexanders pool, hot tub and clothing optional sundecks across the street as well as access to the gym and spa facilities at Key West fitness on Margaret St.

Each of the 2 luxury Villas have a split-level layout (meaning 3 floors), and have 2 bedrooms & 2.5 bathrooms each, all King beds, and all bedrooms are en suites with private balconies and dedicated work/study spaces. The Villas have ultra-modern chef-style kitchens and living rooms with island dining, custom designed cabinetry, and high-end appliances. Both units have parking for 2 cars each (one covere and one uncovered), as well as central A/C & heat and private laundry inside each unit. Guests enjoy private entrances for each unit from Stickney Lane, with a walking path open to Fleming Street.

Stays must be a minimum of 30 nights (or 28 nights in February) – no exceptions due to Key West city ordinance. Stays do not have to be calendar month stays (i.e. The 1^st-31^st of a month), they simply have to be at least 30 consecutive nights. If you are looking to stay for a shorter period of time you are welcome to come and go as you please but your contract must be written for a min of 30 nights and is not transferable. You are welcome to invite outside guests to stay with you (must advise and register any overnight guests with Management) Rates are based on a nightly rate not a monthly rate which is cleared outlined durning the quote process prior to booking a stay. Please visit www.island-mates.com for more information or to submit a request. You are welcome to book a single month or multiple months in a row.  

The two Villas as well as the front house (Jeff & James’ personal home) will share a large pool with water loungers & swim up bar, jacuzzi, outdoor living room, propane grill, and pool deck with sun loungers. You will also enjoy private access to the Island House Café and pool area directly next door. As a resident staying in the Villas, you are welcome to bring friends to the property as your guests, however, the property will NEVER be open to the general public.

Included in the quoted rental pricing for the first 2 guests (charges apply for additional guests) and paid directly to Island House upon check-in, guests will receive a special membership to Island House, granting access to all resort amenities during their stay including FREE Happy Hour which is typically reserved for hotel guests only. This membership also creates a house account at the resort, enabling convenient posting of charges for the duration of your stay. This includes food and beverage, retail purchases, and massage services. A credit card must be placed on file to activate this house account, and the balance will be charged weekly or monthly based on your spending habits and preferences. If you have been a guest at Island House in the past, your experience as a “member” of Island House while staying in the Villas will be essentially the same. 

Yes! Well behaved pets that are properly socialized around other people and pets are welcome to stay with a refundable pet deposit, and a non-refundable pet cleaning fee. Please note that all pets are required to be on a leash when not inside your Villa, and pets are not allowed in the pool. Any damages caused by a pet will be billed immediately upon discovery.  

Due to our proximity to Island House – we market our rentals to the same clientele and assume the vast majority of our guests will be males who want to enjoy a safe and private clothing-optional environment.  That said since a Villa is your own personal residence for at least a month, and the property is shared with the owners up front, you are welcome to host anyone you want – no matter what gender during your stay. With a simple sign posted poolside, all current residents of the Manor will be able to communicate if the property is occupied by just men, or if you can expect mixed company. Island Mates Manor LLC respects all Florida laws as a place of public accommodation and does not discriminate on the basis of sex.

All reservations will be assessed a base cleaning fee that covers once weekly linen service (fresh bedding, and towels) well as the full cleaning upon departure. Each Villa is equipped with it’s own full-size laundry inside each unit, as well as extra linens and towels in both bedrooms to make your stay more comfortable. If you desire additional services such as more frequent bedding changes, fresh bath/pool towel service, or personal laundry, that can be purchased for an additional fee through the front desk at Island House.  You can make these arrangements prior to arrival or during your stay.

You can visit us online at www.island-mates.com or give a call to the front desk at Island House, they can answer many questions or transfer you to Jeff or James for assistance. You can reach us via email at: reservations@island-mates.com The website has rates and availability listed as well as a way to inquire about a specific time period or even book a reservation request. Please keep in mind that all short term rentals in Florida (30 night minimum stay and less than 6 months) are subject to Florida State Tax as well as Monroe County Bed Tax which is clearly detailed on the website and will be shown if you request a rate quote either via email, phone or via the booking site.

Island Mates Manor will begin accepting reservations for its 2 luxury Villas sometime in late May of 2025 for stays beginning in September 2025. You may contact Island House for general information and basic availability inquiries. However, if you’re ready to proceed with a reservation, the front desk will refer you directly to Jeff & James who will book your reservation personally.