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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
$100-$800
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$795
Fishing Charters
Let a captain do the driving while you do the fishing
$115-$610
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$115-$620
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$95-$240
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$135-$195
Kayaks
Who says you need a motor to have fun on the water?
$135-$170
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
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$160
Top Sailboat Rental Locations Near Key West
Stock Island, Florida
27 boats to rent
Florida Keys, Florida
104 boats to rent
Marathon, Florida
18 boats to rent
Islamorada, Florida
23 boats to rent
Tavernier, Florida
16 boats to rent
Key Largo, Florida
21 boats to rent
Marco Island, Florida
30 boats to rent
North Key Largo, Florida
17 boats to rent
Naples, Florida
55 boats to rent
North Naples, Florida
20 boats to rent
Bonita Springs, Florida
65 boats to rent
Coral Gables, Florida
57 boats to rent
Key Biscayne, Florida
10 boats to rent
Miami, Florida
981 boats to rent
Fort Myers Beach, Florida
55 boats to rent
Sanibel Island, Florida
53 boats to rent
Miami Beach, Florida
387 boats to rent
North Bay Village, Florida
50 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. ⭐️⭐️⭐️⭐️⭐️
LR
Lori
Luxury Lagoon 440 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 Lagoon 440 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
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
THOMAS
Luxury Lagoon 440 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
Los Angeles, California
393 boats to rent
San Francisco, California
75 boats to rent
Miami, Florida
981 boats to rent
Marina del Rey, California
140 boats to rent
Oakland, California
46 boats to rent
Honolulu, Hawaii
48 boats to rent
New York, New York
87 boats to rent
San Diego, California
107 boats to rent
Hitchcock, Texas
63 boats to rent
Texas City, Texas
44 boats to rent
Dania Beach, Florida
255 boats to rent
Charleston, South Carolina
129 boats to rent
Houston, Texas
50 boats to rent
Kemah, Texas
41 boats to rent
Clear Lake Shores, Texas
38 boats to rent
Chicago, Illinois
281 boats to rent
Fort Lauderdale, Florida
277 boats to rent
Newport Beach, California
137 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!
Real reviews from happy Getmyboaters.
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