Fantasy Fest Key West Guide

Fantasy Fest Key West: Where to Stay & What to Know

Key West knows how to throw a party. Fantasy Fest Key West takes that talent to a whole new level.

For 10 days every October, costumes, parades, street parties, live music and larger-than-life island energy take over Key West. In 2026, Fantasy Fest runs October 16–25, with the theme Musical Icons and Iconic Musicals.

And at Havana Cabana, you can dive into the festivities without even leaving the pool.

Plan Your Fantasy Fest Stay

What Is Fantasy Fest in Key West?

Fantasy Fest started in 1979 as a way to bring a little more life to Key West’s quieter October season. More than four decades later, it has grown into one of the island’s signature annual celebrations.

Expect bold costumes, themed parties, live entertainment, street celebrations and plenty of that anything-goes Key West creativity.

It is colorful. It is playful. And it is very Key West.

What Happens at Fantasy Fest Key West?

There is no single way to do Fantasy Fest.

The official schedule stretches across 10 days, with everything from live music and pool parties to costume events, street celebrations and parades. Signature 2026 events include the Bahama Village Goombay Festival, Fantasy Fest Street Fair, and the huge Saturday-night Fantasy Fest Parade along Duval Street.

Some events are ticketed, others are free, and individual age requirements vary, so check the official schedule when building your plans.

Dive Into Fantasy Fest at Havana Cabana

Fantasy Fest meets Key West’s largest pool.

On Monday, October 19, 2026, Havana Cabana hosts Duck, Duck, Booze, a Fantasy Fest pool party packed with rubber duckies, pool floats, beverage samples, giveaways and plenty of room to get creative with the theme.

The party runs from noon to 4pm, with free admission and entry open to the public.

Stay at Havana Cabana and your Fantasy Fest day can start right outside your room.

Dive Into the Fest

Havana Cabana pool surrounded by palm trees and pink loungers

Day Pass at Havana Cabana

Not staying overnight? You can still join the energy.

Havana Cabana offers day pass access to the pool experience, giving you a way to enjoy Key West’s largest pool, tropical cocktails and a full resort atmosphere even if you are just in town for Fantasy Fest events.

It is an easy way to take a break from the crowds in Old Town, cool off between events or make the pool party part of your festival plan without booking a room.

Get a Day Pass

Poolside Cabanas & VIP Lounging

For a more elevated pool experience during Fantasy Fest, reserve a private poolside cabana. Cabanas offer shaded seating, dedicated space for your group and a comfortable home base right in the middle of the action.

• Day Passes for up to 8 people

• Shaded poolside cabana from 8:00am – 11:00pm

Sofa seating | Lounge chairs | Smart TV | Complimentary bottled water

Reserve a Cabana

Do Not Miss the Fantasy Fest Parade

If there is one night to circle, make it parade night.

On Saturday, October 24, the Deep Eddy Vodka Fantasy Fest Parade takes over Duval Street with elaborate floats, dancing groups and thousands of costumed spectators. The parade steps off at 7pm and is free to watch.

Come early, find your spot and prepare for Key West at full volume.

Costumes, Street Parties & Duval Street

Fantasy Fest is built for creativity.

On Friday, October 23, the Captain Morgan Masquerade March moves through Old Town before joining the Fantasy Fest Street Fair, while the Street Fair itself fills Duval Street with food, drinks, vendors and costumes across Friday and Saturday.

You can plan every event or simply head downtown and see where the island rhythm takes you.

Where to Stay for Fantasy Fest Key West

When the whole island is celebrating, where you stay matters.

At Havana Cabana, you get the Fantasy Fest energy alongside the space to slow things down between events. Spend time around Key West’s largest pool, grab a mojito, refuel with Cuban-inspired bites or wind down with cocktails and live music at Flama Cabana.

When Old Town calls, Havana Cabana’s complimentary shuttle connects guests with downtown Key West, so you can trade poolside paradise for Duval Street without making parking part of the plan.

Then come back, recharge and do it all again tomorrow.