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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
$130-$830
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$5,715
Fishing Charters
Let a captain do the driving while you do the fishing
$170-$570
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$165-$465
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$130-$310
Kayaks
Who says you need a motor to have fun on the water?
$130-$165
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$370-$730
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$135
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90
Top Sailboat Rental Locations Near Key West
Stock Island, Florida
21 boats to rent
Florida Keys, Florida
103 boats to rent
Marathon, Florida
12 boats to rent
Islamorada, Florida
11 boats to rent
Tavernier, Florida
11 boats to rent
Key Largo, Florida
15 boats to rent
Marco Island, Florida
23 boats to rent
North Key Largo, Florida
11 boats to rent
Naples, Florida
48 boats to rent
North Naples, Florida
16 boats to rent
Bonita Springs, Florida
59 boats to rent
Coral Gables, Florida
49 boats to rent
Key Biscayne, Florida
8 boats to rent
Miami, Florida
886 boats to rent
Fort Myers Beach, Florida
64 boats to rent
Sanibel Island, Florida
56 boats to rent
Miami Beach, Florida
316 boats to rent
North Bay Village, Florida
35 boats to rent
Recent Reviews in Key West
BC
Bryan
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Aaron was super fun and extremely knowledgeable. Our group of five has so much fun sailing the rougher, windier seas. We then made for a secluded spot to fish and swim while we waited for sunset. It was a glorious view and truly checked off a bucket list item for me. Bryan - Oregon
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 !
DA
Donald
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Great trip. Aaron has a super nice rig and went out of his way to show us a good time.
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
353 boats to rent
San Francisco, California
83 boats to rent
Oakland, California
50 boats to rent
Marina del Rey, California
125 boats to rent
Miami, Florida
886 boats to rent
Honolulu, Hawaii
42 boats to rent
San Diego, California
108 boats to rent
New York, New York
84 boats to rent
Chicago, Illinois
289 boats to rent
Hitchcock, Texas
54 boats to rent
Texas City, Texas
44 boats to rent
Annapolis, Maryland
53 boats to rent
Houston, Texas
55 boats to rent
Kemah, Texas
44 boats to rent
Clear Lake Shores, Texas
41 boats to rent
Charleston, South Carolina
132 boats to rent
Tampa, Florida
370 boats to rent
Saint Petersburg, Florida
243 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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