902 Whitehead Street ~ Across From The Hemingway House


42nd Phil Peterson’s Key West Poker Run: September 17th – 20th

Poker Run Bikes - Key Lime Inn


Phil Peterson’s Key West Poker Run is not to be missed if you ride, or just want to soak up some biker culture. Usually over 10,000 motorcyclists, and enthusiasts, come out to enjoy the Run, the people, and the beautiful Florida Keys. Along the ride there are multiple stops to draw your hands, enjoy contests, bikini bike washes, food, drinks, and so much more! You don’t want to miss this incredible ride!

We will have a Welcome Happy Hour at our Lighthouse Court Cafe & Mojito Bar from 4-6pm on Thursday the 17th and provide complimentary rags to keep your chrome dust free and looking sharp. When you stay with us you’ll be able sleep close to your bike and all the action on Duval.



36th Annual Key West Fantasy Fest: October 23rd – November 1st

This year’s theme for Fantasy Fest is All Hallows Intergallactic Freak Show‘.   Whew…that’s a lot of possibilities for costumes! We have special room rates starting at $239 per night plus taxes for Goombay Festival on the 23rd & 24th, the Zombie Bike Ride on the 25th, the Burlesque Parody on the 26th and the Tighty Whitey Party on the 27th (look out Magic Mike!) For reservations and information please call 800.549.4430  All of our 6 Historic Key West Inns hotels are located in walking distance to the Fantasy Zone.  

Fantasy Fest Key West Cypress HouseMasquerade March – Friday, October 30th

DJ’s Scott and Jimmy will be at our two hotels in Old Town again here again this year pumping up the party at Chelsea House Hotel & Merlin Guesthouse for the Masquerade March on Friday, October 30th from 5 -7:30PM. The March is a walking parade for anyone who wants to join, either in costume or not. The parade starts at the Key West Cemetery and takes two different routes to Duval Street. Luckily, we have hotels on both routes! The Truman Avenue March goes past our Chelsea House Hotel and the Fleming Street March goes past our Merlin Guesthouse and at both hotels we set up a bar that serves our coveted rum punch! This is always a really crowded and fun event and we never know exactly how much punch to make……so we just make a lot!!! We never have leftovers and everyone dances away feeling verrry happy!

Fantasy Fest Parade – Saturday, October 31st

The famous Fantasy Fest Parade follows on Saturday night. Join 70,000 of your friends as it heads down Duval street with outrageous  costumes, fabulous floats, dancers and the music makers. It’s a wild and crazy time!


Parrotheads 24th Annual Meeting Of The Minds In Key West: November 4th – 8th

Kelly McGuire Parrotheads Lighthouse CourtFans of Jimmy Buffett come to Margaritaville for their annual “Meeting of the Minds” convention. Join us for our free Parrothead Events at our Lighthouse Court Hotel, 902 Whitehead Street, when we will have our 10th Annual Songwriter’s Garden Concerts with Kelly McGuire & Friends, every afternoon from 2 to 5pm for happy hour specials. The concerts are open to all guests of Historic Key West Inns hotels so come relax around the pool, sip on a Key Lime Margarita, sing along with Kelly and get your latitude adjustment on!

Hotel Availability for MOTM

Rooms are filling up for the main dates of MOTM. Rates at our hotels in Old Town for this year’s Parrothead’s events start from $199 per night plus taxes. For reservations and information please call 800.549.4430 


35th Key West Superboat Powerboat Championship Races: November 8th – 15th

Superboats Racing Championships Key West HarborThe Key West World Championship Race takes place in Key West in November.   If you haven’t seen powerboat racing before, you will not believe the excitement from the roar of these boats racing through the harbor. The viewing stands are right in front of the action. The Key West race is the culmination of a year of racing for the teams. You will see the biggest, the fastest, and the best.

Race Village, with the Wet Pits, Dry Pits, and race viewing, is at the Truman Waterfront on the western shore of Key West. All of our 6 Historic Key West Inns hotels are located within walking distance of Race Village. Race week begins with a parade of Superboat’s down Duval Street on Sunday, Nov 8. Race days are Wednesday, Friday and Sunday, Nov 11, 13, and 15. Rates at our hotels in Old Town for this year’s Superboat’s events start from $299 per night plus taxes. Call us today for your reservation 800.549.4430



Key West Film Festival: November 18th – 22nd

Key West Film Festival 2015Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The four-day program includes films from multiple genres and categories, as well as, social events with filmmakers, actors and film lovers.

Rates at our hotels in Old Town for this year’s Film Festival events start from $249 per night plus taxes. Call us today for your reservation 800.549.4430


Thanksgiving Weekend In Key West: November 26th – 28th

Come Bike on the Beach

Start a new family tradition for Thanksgiving by riding your bicycle or walking to dinner, just like the locals in Key West do! Sit outside under palm trees, warm breezes on your shoulders, the suntanned, smiling faces of our your family and friends around the table. For something romantic, you can head to the beach with your bike basket full of gourmet treats, fresh fruit, and a bottle of wine, all secured with bungee cords. Be creative, let your imagination create the fun for your new tradition. Rates at our hotels in Old Town start at $239 per night. Call us today for your reservation 800.549.4430

DAILY: Enjoy poolside food & cocktail Happy Hour at our Lighthouse Court Cafe & Mojito Bar from 4 – 6pm.  Come try our delicious drinks or play a game of Cornhole on our backyard court with your family & friends. It will get competitive before you know it and you’ll have a blast!



Red Barn Theatre: Ongoing

Red Barn sets the bar for really great theatre in Key West. Works by Bob Bowersox, Mike Marrero, Mike Craver, Debra Monk, Mark Hardwick, Mary Murfitt, Charles Busch, Nora Ephron & Delia Ephron, Eric H. Weinberger and Donald Margulies have audiences laughing, crying, singing and generally just having a great night out. Get more info about the Red Barn Theatre here. Start your evening off with a Sour Coconut coconut Bacardi white rum and lime, at our poolside Mojito Bar  and then head out to the barn for the performance.

Enjoy poolside Happy Hours at Lighthouse Court Cafe & Mojito Bar from 4 – 6pm. Maureen will be happy to make you a Sex on the Sand or your favorite libation! Come try our delicious specialty drinks or just relax the day away under the sunshine by the pool with your family & friends.