Wonder what Chaddd has going on under that towel… 😈 #BestGayResortInTheWorld

Island House is turning 50 years old this year and we are celebrating with Gold Pool Parties each month for all of 2026! Plus, in May, we will hosting our Big Anniversary Weekend with more details to come on that soon! 🎊🪩 #BestGayResortInTheWorld #50YearsOfFabulous

Yesterday at our Boys & Bubbles Pool Party, we shared that Island House is turning 50 years old this year! So cheers to 50 years of fabulous! And as we enter our golden era, we can't wait to celebrate with all of YOU! Be sure to checkout our schedule of Gold Pool Parties happening monthly!! 🫶 💛

Imagine being here for Midnight Mass… ✨

All sorts of fun all over Key West! So come join us on our gay little island!! 🏝️

@dronedik.bsky.social hanging out with us late at night… did we mention our poolside cafe is open 24 hours a day!

Come and play with me and Alex Tikas at WOOF Week in Key West in April 2026. Right now you can use my exclusive 10% discount code WOOFJASON for 10% off the Super Early Bird Rate passes. @bearworldmag.bsky.social @islandhousekeywest.com All the info: woof-week.com

A beautiful full double moon at the #BestGayResortInTheWorld

Who’s thirsty? 🥵 #BestGayResortInTheWorld

🐻✈️ In Ep. 10, @raviroundtheworld.bsky.social visits Honolulu, a place where you can be uniquely you without fear or backlash. Māhū tradition is being reclaimed and woven into Queer identity in Hawai'i 🏝 Sponsored by: @islandhousekeywest.com 📺: youtu.be/_g-ZzQ4mySE

The Red Room at @islandhousekeywest.com was so 🔥last night that @yournewdadxxx.bsky.social and I had to take a break with our new friends part way through to refuel for round 2!

🐻✈️ In Ep. 9, @raviroundtheworld.bsky.social does Dallas as he explores the BIG D! Dallas is a city where you can truly expect the unexpected, and it radiates so much queer joy, it celebrates three Prides! 🏝 Sponsored by: @islandhousekeywest.com 📺: youtu.be/2xBUAqigqtM #BearWorldTV #lgbttravel

The happiest birthday to our wonderful owner Bobi Lore, who helps keep our island very gay 365 days a year! 🏝️🏳️‍🌈 #BestGayResortInTheWorld

🐻✈️ In Ep. 7, @raviroundtheworld.bsky.social takes us to his favorite city, San Francisco 🇺🇸🌉✨ Famous for the Golden Gate Bridge, the soul of the city lives in its neighborhoods - including a leather district and a transgender district! 🏳️⚧️ 🏝 Sponsored by: @islandhousekeywest.com 📺:

The best of Bear World TV is BACK! 🎉 Watch the moments from the past 6 weeks all in one place. World-traveling bear @raviroundtheworld.bsky.social shares quick takes on his latest adventures — from the W Hotel in West Hollywood to @islandhousekeywest.com 🏝 📺: youtu.be/ra9rpnQ3L_c #BearWorldTV

Happy National Bowtie Day! @islandhousekeywest.com

You never know what you’re going to see at Island House! 👀 @milomilesx.bsky.social

@raviroundtheworld.bsky.social takes on NYC — From resilience born on 9/11 to the chaos, dreams, and nightlife that never sleeps, celebrate the raw & radiant spirit of New York. 🌃 Watch his latest rave on Bear World TV → youtu.be/ZNR4ZeYPgsQ Sponsored by @islandhousekeywest.com #BearWorldTV #NYC

In episode 3, our world-traveling bear @raviroundtheworld.bsky.social takes you to the most glorious national park, the queerest town in Delaware, and shares the best credit card tips. 🌍 🎥 Watch more on Bear World TV. 👉 youtu.be/2e6nJB-eI1A Sponsored by @islandhousekeywest.com #BearWorldTV

Just how we like it… 🙌🥵 📸 by Larry Blackburn #BestGayResortInTheWorld

🌍🐻 In Ep. 3, our globe-trotting bear @raviroundtheworld.bsky.social spills on his fave clothing-optional beach in NYC, why Key West is a must for bear travel, & all the fun of Belgium Bear Pride. ✈️✨ 🎥 Watch: youtu.be/Sv9UxKpAw2w 🏝️ Sponsored by: @islandhousekeywest.com #BearWorldTV #Travel

A special Pool Party Saturday for our Tropical Heat visitors! 😉

In episode 2, world-traveling bear @raviroundtheworld.bsky.social shares highlights from Vancouver Pride, São Paulo, and Key West Bear Weekend—plus flying tips for bears and his Travel Bears of the Week. 🐻✈️ Sponsored by @islandhousekeywest.com youtu.be/-JK0lBvo39A #BearWorldTV #BearTravel

Things are getting wild at the Pink Pool Party! 🩷 #BestGayResortInTheWorld

Tropical Heat officially kicks off tomorrow!! 🙌 And all the fun starts at Island House, for our Cowboy Ken’s Pink Pool Party! 🩷 We can’t wait to see everyone at 5pm! 🤠 #BestGayResortInTheWorld

@islandhousekeywest.com in Key West is more than a resort; it’s a sanctuary, a legendary home base for bears, cubs, and their admirers who come from all corners of the globe to unwind, connect, and celebrate our shared brotherhood - especially as host of @keywestbears.bsky.social buff.ly/KRUJHHD

@islandhousekeywest.com in Key West is more than a resort; it’s a sanctuary, a legendary home base for bears, cubs, and their admirers who come from all corners of the globe to unwind, connect, and celebrate our shared brotherhood - especially as host of @keywestbears.bsky.social buff.ly/KRUJHHD

🐻 In this debut episode on Bear World TV, @RaviRoundTheWorld.bsky.social visits the W Hotel in West Hollywood, Island House in Key West, names his travel bear of the week, and shares upcoming world bear events! Watch now: youtu.be/ra9rpnQ3L_c Sponsored by @islandhousekeywest.com

We are SO excited to share that starting on Thursday, August 7th, we are officially launching Bear World Television! This project comes with a lot of love and hard work, specifically from our five dynamic hosts! #BearWorldTV

Pup Ryder, can we just go back nows? #puppyplay #pupgear #gaypup #gay #puphood #pupplay #gaypupplay #islandhouse @pup-ryder79.bsky.social @islandhousekeywest.com

In this picture you’ll find local business owners, bartenders, kings, queens, politicians, police officers, activists, neighbors, friends, and most importantly LOVE. THIS is why we CALL KEY WEST HOME! Because our island community stands up for each other! 🫶🏳️‍🌈 📸 by Nick Doll #BestGayResortInTheWorld

today’s look for the pool party at @islandhousekeywest.com — #gay #ass #thong

When you are 0 feet away from the #BestGayResortInTheWorld 🏝️ 📸 by @zandjtravel #IslandHouseKeyWest

Happy Pride Month from some of the hottest Daddies of early June 🔥 We’ll be featuring some of our favorite Dads throughout Pride Month. Tag your favorites below ⬇️⬇️ @islandhousekeywest.com @daddyland74.bsky.social Find your Daddy on the Daddyhunt app: daddyhunt.onelink.me/BKy2/gko2yfes #daddyhunt

Just enjoying another sunny day in paradise! 😎🌴 📸 by @remarkcentral #BestGayResortInTheWorld

“We needed something to express our joy, our beauty, our power. And the rainbow did that.” - Gilbert Baker, creator of the original rainbow flag 🏳️‍🌈 #BestGayResortInTheWorld

The world is going to shit, but I've got a long pour of Woodford and Maryland Pride and Fetish Pride flags from @flagsforgood.com in my slider at @islandhousekeywest.com while the hubs and I spend a week relaxing with the pup and friends.

Follower on insta sent me this. The illegal homophobic fences at Dupont Circle are coming down! It’s a Pride Miracle!

Thank you!! 🩷

We are extremely sad to share that one of our longest serving Front Desk Mates and dear friend, Gordon Ross, passed away earlier today. We have lost a Key West legend! Remember to keep living your best adventures, because that is what Gordon would have wanted! 💙 #LoveYouGordonRoss

Some resorts give you a room. @islandhousekeywest.com gives you a whole community. 24/7 pool access, clothing-optional freedom, and some of the kindest guys you’ll ever meet. Your vibe is waiting 🔗 rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈

Happy Monday from Key West! 🤪 #BestGayResortInTheWorld

If you leave @islandhousekeywest.com with tan lines, that’s on you. Get the full experience: rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈

At @islandhousekeywest.com, friendships start with “Where you from?” and end with “See you in the red room.” Meet your people: rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈

@islandhousekeywest.com isn’t about being perfect. It’s about being free. (And maybe a little flirty.) Explore: rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈

We hope your Monday is going as good as ours! 😈 🏝️ 📸 by @diesel_dave_tpa #BestGayResortInTheWorld

The drinks are cold. The men are warm. The swimsuits? Optional. Explore the @islandhousekeywest.com fantasy: rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈

🐾 WOOF Week 2025: Sun, Fur, and Seriously Sexy Vibes in Key West 🌴🍑 @islandhousekeywest.com #WoofWeek2025 bearworldmag.com/key-west-woo...

Your next vacation needs less fabric, more flirting. @islandhousekeywest.com knows the assignment: rebrand.ly/597i60f #ad #GayTravel #LGBTQtravel 🏳️‍🌈