Best 568 things to do in Longboat Key, FL

Cruise sandbars and islands on a clean, fully loaded pontoon

Ride around Holmes Beach with a safety briefing and life jackets included

Scan Sarasota's coastal waters for dolphin sightings by jet ski

Rent a street-legal 6-passenger golf cart with delivery included

Paddle a tandem kayak from the canals to Tampa Bay

Rent cornhole for easy, all-ages beach-day fun

Play Slammo at the beach with a 1–7 day rental

Rent a street-legal 8-passenger golf cart with delivery included

Rent a beach cruiser with delivery, helmet, and lock included

Bring music and evening lighting to your group ride

Paddle Anna Maria canals or venture into Tampa Bay

Roll across sandy beaches with balloon tires

Cruise 70 miles to Dry Tortugas to explore Fort Jefferson and snorkel clear waters

Shape a shaded Key West boat day around your crew's interests

Target reef species offshore with AM or PM options

Target snapper, grouper and more on an offshore fishing trip

Feed fish from a clear-bottom kayak with underwater LED lights in Sarasota

Cruise Siesta Key by e-bike with a rental timed for sunset

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.

Explore Siesta Key with room for your belongings

Explore Siesta Key on a street-legal scooter built for two

Explore Siesta Key at your pace with flexible golf cart rental times

Choose a bike style and rental length for easy Siesta Key exploring

Get out on the water with free delivery on Siesta Key