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The Best Sailboat Rentals in Key West
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Key West
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$145-$1,140
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$900
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$500
Kayaks
Who says you need a motor to have fun on the water?
$100-$1,100
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$125-$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$160
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$130
Top Sailboat Rental Locations Near Key West
Recent Reviews in Key West
LR
Lori
Luxury Sailing Catamaran in Key West
Awesome boat!! Ashley was very helpful and easy to communicate with. Nils, the captain was very welcoming and informative as we cruised around looking for sea life. We saw turtles, dolphins and even a hammerhead shark. It was such a relaxing day. Thanks Ashley and Nils for making our day great.
JA
Jody
Luxury Sailing Catamaran in Key West
Five stars isn't enough! The catamaran is beautiful, and the crew was extremely accommodating. Captain Nils and First Mate Patrick are top notch seamen and gentlemen to boot. Took us to all the best spots to enjoy the beauty and majesty of Key West!!! We cant recommend them highly enough!
CD
Carina
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sunset Cruise was responsive throughout the entire process & more than accommodating. Both Eric & Mark were with us through our experience & were nothing but pleasurable and made the day great. I highly recommend Sunset cruise & this boat !
Alex
41' Island Trader Ketch in Key West, Florida!
We had an absolutely amazing experience out on the boat. The captain and crew were amazing and so kind and accommodating. The dog was the cherry on top too - cutest thing ever.
Bobby
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Great owner and communications the captain Nate and first Mate Mark were wonderful , would highly recommend Hightide for a nice sail or snorkeling
THOMAS
Luxury Sailing Catamaran in Key West
We charter often when on vacation but this was by far the best! Beautiful boat, amazing captain and crew! Incredible experience.
Top Sailboat Rental Locations in the United States
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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