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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
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$145-$920
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$885
Fishing Charters
Let a captain do the driving while you do the fishing
$155-$565
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$155-$585
Kayaks
Who says you need a motor to have fun on the water?
$135-$175
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$135-$310
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$95-$240
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$135
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$750
Top Sailboat Rental Locations Near Key West
Stock Island, Florida
22 boats to rent
Florida Keys, Florida
94 boats to rent
Marathon, Florida
18 boats to rent
Islamorada, Florida
20 boats to rent
Tavernier, Florida
14 boats to rent
Key Largo, Florida
19 boats to rent
Marco Island, Florida
25 boats to rent
North Key Largo, Florida
15 boats to rent
Naples, Florida
46 boats to rent
North Naples, Florida
12 boats to rent
Bonita Springs, Florida
56 boats to rent
Coral Gables, Florida
54 boats to rent
Key Biscayne, Florida
11 boats to rent
Miami, Florida
1012 boats to rent
Fort Myers Beach, Florida
61 boats to rent
Sanibel Island, Florida
56 boats to rent
Miami Beach, Florida
374 boats to rent
North Bay Village, Florida
44 boats to rent
Recent Reviews in Key West
Brandon
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Highly recommended Captain Aaron and his crew Brook... they did an amazing job of hosting and tending to our wants. Very nice boat with ample toys and things to do on the water. Will definitely join them again. ⭐️⭐️⭐️⭐️⭐️
CD
Carina
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 !
Bobby
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
JF
Jessica
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
We spent four hours as a family together - it was a great adventure. I highly recommend this experience!
JS
Jad
Captained 80' Sailing Schooner Charter In Key West, Florida
Amazing ship, a piece of history, great crew, and an excellent experience. Highly recommended!
Maggie
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
We had the BEST time ever, wouldn’t change a thing!!! Absolutely book this immediately!
Top Sailboat Rental Locations in the United States
Los Angeles, California
348 boats to rent
Miami, Florida
1012 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
126 boats to rent
Honolulu, Hawaii
47 boats to rent
Oakland, California
43 boats to rent
San Diego, California
111 boats to rent
New York, New York
79 boats to rent
Annapolis, Maryland
47 boats to rent
Dania Beach, Florida
234 boats to rent
Fort Lauderdale, Florida
254 boats to rent
Chicago, Illinois
258 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Charleston, South Carolina
126 boats to rent
Long Beach, California
82 boats to rent
Houston, Texas
52 boats to rent
Kemah, Texas
41 boats to rent
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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Real reviews from happy Getmyboaters.
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