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The Best Sailboat Rentals in Florida Keys
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Florida Keys
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$820
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$1,800
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$835
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$110-$1,800
Kayaks
Who says you need a motor to have fun on the water?
$100-$195
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$150-$295
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$725
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$135
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$160
Top Sailboat Rental Locations Near Florida Keys
Stock Island, Florida
22 boats to rent
Key West, Florida
42 boats to rent
Marathon, Florida
22 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
47 boats to rent
North Naples, Florida
12 boats to rent
Coral Gables, Florida
54 boats to rent
Key Biscayne, Florida
11 boats to rent
Bonita Springs, Florida
59 boats to rent
Miami, Florida
1026 boats to rent
Miami Beach, Florida
372 boats to rent
North Bay Village, Florida
45 boats to rent
North Miami, Florida
164 boats to rent
Fort Myers Beach, Florida
62 boats to rent
Recent Reviews in Florida Keys
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. ⭐️⭐️⭐️⭐️⭐️
JB
Jessi
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Fantastic trip, gorgeous boat, great crew!
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
362 boats to rent
San Francisco, California
75 boats to rent
Miami, Florida
1026 boats to rent
Marina del Rey, California
132 boats to rent
Honolulu, Hawaii
46 boats to rent
Oakland, California
43 boats to rent
San Diego, California
112 boats to rent
New York, New York
77 boats to rent
Annapolis, Maryland
47 boats to rent
Dania Beach, Florida
236 boats to rent
Fort Lauderdale, Florida
255 boats to rent
Chicago, Illinois
261 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Charleston, South Carolina
128 boats to rent
Tampa, Florida
420 boats to rent
Newport Beach, California
124 boats to rent
Houston, Texas
52 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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Florida Keys Boating Guide - Getmyboat
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December 30, 2019
Miami Boating Guide - Getmyboat
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Getmyboat's Guides to the World of Boating
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Real reviews from happy Getmyboaters.
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