• 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] 

Close up of a Carrick Bend Mat

National Maritime Day

Saturday, May 22, 12pm-2pm

Do you have what it takes to be a seafarer? Find out with our Knot tying class! Come out to Shipwrecker’s pool bar at 12pm where we’ll teach you how to tie all the popular knots used by sailors. Listen to stories told by a local historian and enjoy drink specials from the bar!

people clinking two wine glasses together

National Wine Day

Tuesday, May 25

Celebrate National Wine Day with us at Shipwrecker’s Pool Bar! Our very own GM will be conducting a wine tasting at 5pm and we will be serving hors d’oeuvres.

Burger with brie cheese and mushrooms and a beer

National Burger Day

Friday, May 28

Facts: Burgers are even more delicious when enjoyed poolside in paradise! To celebrate National Burger Day, we will be serving up dry-aged burger specials and flights of local beers all day at Shipwrecker’s bar!

man with long blond hair bicycling at the beach

Sunset Island Bike Tour

Thursday, June 3

Celebrate World Bicycle Day in Key West this summer! Hop on a bike, let the summer breeze flow through your hair and learn some history along the way. Rent a bicycle from our onsite concierge for 50% off and join us outside the lobby at 7pm as we get ready to head out on a sunset island tour. The tour will be lead by a local historian, and we’ll stop by all of the interesting and historic landmarks in Key West. Be sure to check out our Key West Adventure Package that comes with bike rentals for two daily!

A woman relaxes poolside at a Key West resort with a drink

National Rosé Day

Saturday, June 12th 

Rosé all-day? Sounds good to us! We’ll be celebrating with Rosé welcome drinks at check-in, Rosé poolside popsicles and Rosé all-day drink specials!

child and his dad on a hammock

Father’s Day

Sunday, June 20

Calling all dads! Come out to our pool where we’ll be celebrating your special day all day! We’ll have a poolside DJ from 12pm-6pm, $3 draft beers all day and prime steak specials for lunch and dinner!

Kids in mermaid tails sitting poolside

Key West Mermaid Festival

July 1 – July 5 – Havana Cabana 

Join us at our sister property Havana Cabana for the 2nd annual Key West Mermaid Festival! Barbary Beach House guests can take the resort shuttle and enjoy four days full of festivities at the largest pool in Key West! There will be music, games, vendors, and fintastic food and drink specials! This event is free to attend, guests must purchase tickets for the Swim with Mermaids event. Check out the times and activity schedule below!


A woman in a mermaid tail sitting poolside

Meet the Mermaids Pool Party- Havana Cabana

July 1 – 11am-4pm

Meet the Mermaids and King Neptune under the Havana Cabana tiki hut from 11am-12pm. Ask them questions and take shellfies with them!

Swim with the mermaids from 12:30pm-2:30pm! Children will get to wear their very own tails and swim one on one with the pod. Tickets need to be purchased to be able to swim with mermaids.

After the one-on-one swimming lessons are complete, there will be an open swim with the mermaids from 3pm-4pm for anyone that wants to join!

Green mermaid tail in a pool

Meet the Mermaids Pool Party- Havana Cabana

July 5 – 10am-2pm

Join us again on the last day of the Mermaid Festival for another swimming with the mermaids event from 10am-2pm!

A woman painting outside at a Sip & Paint event in Key West

Sip & Paint

Monthly, Saturdays at 6:00pm

March 27th, April 17th, May 1st, June 5th, July 17th, August 14th, September 18th, October 16th.

Come out to our beautiful Shanty Tiki for our monthly Paint & Sip classes! Each class will be themed and everything is included! We provide the supplies, the art instructor and the wine! To see each month’s date and special theme, visit our Adult Activities page.

Reservations highly encouraged. Please email us below with the number of people in your party, your name and which date you’d like to reserve for.

  • Off to a new Adventure?

    Before you go, sign up to get our newsletter straight to your inbox.

  • This field is for validation purposes and should be left unchanged.