Explore Things to Do in Key West
There is always something unfolding in Key West, even if that something is blissfully relaxing. Step beyond our doors to the energy of Mallory Square, wander the colorful lanes of Old Town, or drift up vibrant Duval Street. Retreat to your private balcony, settle into sunlit serenity at our waterfront pool, or surrender to restoration at SpaTerre—just steps away, yet worlds apart.
Activities
Key West Activities & Attractions
From jet skiing and sun-soaked beaches to gallery hopping and historic sites, there are endless ways to play during your stay. Explore the best things to do in Key West.
Amenities
Just Add Sunshine
Oceanfront pool time, a little boutique browsing and blissful spa escape, all without leaving the resort.
Calendar of Events
Key West is abuzz year-round with lively festivals and celebrations. Keep a close eye on our calendar so you don’t miss a moment of the fun.
Oct19Mrs. Roper Romp, Costume Contest
Get your caftans ready and that signature curly red wig for a groovy costume party on Sunset Pier.
Date: October 19, 2026
Time: 5:00 PM
Location: Sunset Pier
Oct20Savor the Season
Celebrate Sober October with Ocean Key Resort and Best Day Brewing.
Date: October 1, 2026 - October 31, 2026
Time: All day
Location: Sunset Pier
Oct20Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct20Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - December 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Oct20Tay Tay Tuesday, Life of a Showgirl
Join us for a family-friendly tribute to your favorite musical icon and showgirl.
Date: October 20, 2026
Time: 6:00 PM
Location: Sunset Pier
Oct21Live at Sunset Pier – DJ Scott Gerke
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: Daily: October 21 - 24, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Oct21Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: October 7, 2026 / October 14, 2026 / October 21, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier
Oct22SpaTerre VOYA Treatments
Relax and rejuvenate the natural way! VOYA Organic Seaweed Treatments.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, All day (by appointment)
Location: SpaTerre
Oct22Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Oct22Romance at Hot Tin Roof
Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, During Hot Tin Roof dining hours
Location: Hot Tin Roof
Exclusive Guest Experiences
Only at Ocean Key
Experience the best of Key West through our exclusive programming. We’ve curated every detail to ensure you make the most of your vacation.