Couple descending wooden ship-themed stairway with nautical decor.

Things to Do

In The Florida Keys, adventure is just a footstep (or paddle, or fin) away. Whether you’re chasing sunrise paddle-trips, sunset sails, or discovering hidden mangrove tunnels, there’s always something new to try. Museums, wildlife tours, water sports, quirky local events—every destination brings its own flavor of fun. These listings span every kind of experience: rugged and wild, soft and serene, absurdly beautiful. So map out some time, pack your curiosity, and let the Keys pull you in.

Filters
Keys Season Deals
Destination
Category
Islamorada

Caribee Marina

Caribee Boats Marina — full-service marina and boat sales in Islamorada, where 75+ years of Keys boat-lifestyle expertise meets prime waterfront access.

Islamorada

Lignumvitae Key Botanical State Park

Lignumvitae Key: boat-access tropical hammock and historic Matheson home.

Islamorada

IslaMarina

Full-service marina / rentals hub in Islamorada.

Islamorada

KeyZ Charters

Explore the Florida Keys with KeyZ Charters—unique boat tours, snorkeling, and sunset cruises!

Islamorada

Safe Harbor Angler House

Secluded marina sanctuary with luxury lodging, sportfishing, pool, and events.

Islamorada

Michelle Nicole Lowe, Artist

Michelle Nicole Lowe creates vivid watercolors and gallery art in Islamorada, celebrating Keys marine life and conservation.

Islamorada

Three Waters Resort & Marina

Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.

Meetings Max
120
Total Space
1680 sq ft
Largest Room
1680 sq ft

Islamorada

Elena Madden Studio Gallery

Elena Madden creates vibrant contemporary photography and mixed-media art inspired by nature and the coastal landscape.

Islamorada

Captain Michael Fishing

Captain Michael Party Boat Fishing offers affordable, group-friendly deep-sea fishing trips aboard a 65-foot vessel, departing daily from Robbie’s of Islamorada.

Islamorada

Allergic to Land Charters

Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.

Islamorada

Kraken's Lair Diving

Dive Kraken's Lair: Keys PADI center with charters, gear, training.

Islamorada

Whale Harbor Marina

Whale Harbor Marina — premier full-service marina and charter hub in Islamorada, Florida Keys.

Islamorada

Reef Roamer Catamaran Snorkel Sail

Catamaran snorkeling tours exploring Key Largo’s coral reefs.

Islamorada

Latitude Charters

Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.

Islamorada

Scuba Town USA

Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.