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The Best Sailboat Rentals Near Leeward Islands
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Leeward Islands
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$95-$1,315
Kayaks
Who says you need a motor to have fun on the water?
$30-$210
Diving
Explore the ocean depths with trained boat operators
$95-$1,315
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$235
Fishing Charters
Let a captain do the driving while you do the fishing
$80-$235
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$120-$125
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$1,400
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$210
Top Sailboat Rental Locations Near Leeward Islands
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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