The Beach Weekend KW
25' Pontoon — 12 Passenger
Family sandbar day, easy driving
One mile east of Key West. Where the working boats live.
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Rentals · 20 listings
Listings from local rental operators. Check each operator's requirements before you book.
The Beach Weekend KW
Family sandbar day, easy driving
The Beach Weekend KW
The Instagram boat — waterslide and upper deck
The Beach Weekend KW
Fishing setup out of Stock Island
The Beach Weekend KW
Waterslide fun, smaller footprint
The Beach Weekend KW
Tiki bar on the water, plus a slide
The Beach Weekend KW
Take a boat every day of your stay
The Beach Weekend KW
Their signature pontoon package
The Beach Weekend KW
Serious open-water rig for small groups
Sunset Watersports
Widest fleet in KW — deck boats, pontoons, whalers
Sunset Watersports
Half-day version of the same fleet
Boat Rentals in Key West
Small couples-friendly boat, easy to handle
Boat Rentals in Key West
Reef fishing and beyond
Boat Rentals in Key West
Party pontoon with upper deck

Boat Rentals in Key West
Deck boat for sandbar and cruising

Boat Rentals in Key West
Tritoon stability for the sandbar

Hurricane Hole Key West
Fishing setup, near-shore and reef

Hurricane Hole Key West
Their flagship rig — offshore-capable

Hurricane Hole Key West
Smaller center console, still ocean-capable

Hurricane Hole Key West
Nimble fishing skiff for two to four

Hurricane Hole Key West
Pontoon out of Hurricane Hole
Deck · fishing
Reef, backcountry, and offshore charters with local captains.
Deck · snorkel
Barrier reef snorkeling — gear included, no experience needed.
The Beach Weekend - Key West
Stock Island · Check live times
The Beach Weekend - Key West
Stock Island · Check live times
Deck · sandbar
Half-day sandbar cruises to the Marquesas and beyond.
Six Fins Boat Charter - Perry Marina
Stock Island · Check live times
Wall to Wall Fishing Charters
Stock Island · Check live times
Deck · boat rental
Bring your own captain or DIY on a self-drive boat.
Deck · paddle
Kayak the mangroves or SUP the flats.
The Beach Weekend - Key West
Stock Island · Check live times
The Beach Weekend - Key West
Stock Island · Check live times
Deck · sunset
Watch the sun drop over the Gulf with drinks in hand.
Deck · scuba
Two-tank reef dives, wreck dives, and Discover Scuba.