• couple man and woman floating in pool

Parties & Events

Join us for our seasonal parties and special events! From Christmas Trivia, to live concerts and Summer Kick Off Pool Parties, our events are sure to put you in the seasonal party mood! All of our events are included at no additional charge to our guests. Guests from Barbary Beach House and Havana Cabana are welcome to attend events ate either property, and can get to the properties by taking our shuttle. For more information on our events contact Amy at [email protected] 

a man singing

The Swayzees Poolside Concert

Saturday, December 19th 8pm
Held at Havana Cabana  
Come out to the largest pool in Key West and enjoy a live concert by one of the best local bands around! The Swayzees will be preforming from 8am to 10pm. There will be games, delicious food specials and specialty cocktails! Throw on your bathing suit and hop on the shuttle, this is a concert you don’t want to miss!

a seashell with christmas ornaments

Christmas Trivia

Wednesday, December 23rd 8pm
Show off your Christmas fact knowledge! 
This special edition of trivia is Holly and Jolly! Bring your family and friends to be crowned the trivia Kings/Queens of Christmas! Trivia starts at 8pm under the tiki. Unlimited Egg Nog & all you can eat Christmas cookies! Sing a long Christmas Carols and surprise gifts added into the fun! Just thinking about it makes us MERRY!

a bowl of christmas cookies

Christmas Cookie Throw Down

Thursday, December 24th 11am
Held at Havana Cabana  
Do you think you have the best cookie around? Do you think you can go to sprinkle to sprinkle with guests from all over the world and their signature cookies? Then come out to our Christmas Cookie Throw Down! Join us poolside Christmas Eve morning 11am sharp at Havana Cabana. Cookies will be eaten (and judged) along with complementary coffee. Prizes for 1st, 2nd and third best cookies will be awarded!

bowl of candy canes

Candy Cane Hunt

Saturday, December 26th 4pm
Hunt for candy canes and win prizes! 
Our Barbary Beach House garden will be turned into a Winter Wonderland filled with hundreds of candy canes! Come out and hunt for candy canes hanging from our coconut trees. Fill your goody bags and win great prizes!

a snowman made out of sand on the beach

Build a Tropical Snowman

Sunday, December 27th 3pm
Join us for an epic beach adventure!
Do you think you can build the ultimate snowman…I mean Sandman?! Come on down to the Shanty Tiki Hut at 3pm, we will make our way to Smather’s Beach where the competition will begin. Contestants are welcome from both Havana Cabana and Barbary Beach House. Each team may create their sandman however they desire within a two hour window. Judges will hit the beach at 5pm, and prizes will be awarded for the most creative, the most jolly and the most tropical!

A woman dressed in a white outfit celebrates with a drink at Barbary Beach House Key West

White Out 2020

Thursday, December 31st 1-4pm
Dance, Drink & Say GOODBYE to 2020!
Join us in your all-white outfit and help us white out 2020! Pre-game with us at the Shipwreker’s pool deck from 1pm-4pm. We’ll have a champagne station at check-in, specialty cocktails and a DJ! Continue the party by taking our shuttle to Havana Cabana for our Glow Party from 4pm-8pm. There will be great food specials, music and of course; the largest pool in Key West!

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