Cookies & Agreements
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
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
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$1,870
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$1,940
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$60-$590
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$135-$1,120
Kayaks
Who says you need a motor to have fun on the water?
$50-$930
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$65-$320
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$150-$225
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$125-$170
Diving
Explore the ocean depths with trained boat operators
$75
Top Sailboat Rental Locations Near Florida Keys
Stock Island, Florida
24 boats to rent
Key West, Florida
41 boats to rent
Marathon, Florida
20 boats to rent
Islamorada, Florida
25 boats to rent
Tavernier, Florida
15 boats to rent
Key Largo, Florida
22 boats to rent
Marco Island, Florida
32 boats to rent
North Key Largo, Florida
18 boats to rent
Naples, Florida
58 boats to rent
North Naples, Florida
20 boats to rent
Coral Gables, Florida
49 boats to rent
Key Biscayne, Florida
9 boats to rent
Bonita Springs, Florida
68 boats to rent
Miami, Florida
947 boats to rent
Miami Beach, Florida
394 boats to rent
North Bay Village, Florida
53 boats to rent
North Miami, Florida
184 boats to rent
Fort Myers Beach, Florida
53 boats to rent
Recent Reviews in Florida Keys
Brian
22ft Sea Fox 226 Commander for Family fun or Fishing!
Great boat, great service. Professional and prompt with everything. Went above and beyond to make sure everything went smoothly and as planned. Would highly recommend. Great boat, speakers, etc.
MD
Michael
22ft Sea Fox 226 Commander for Family fun or Fishing!
Absolutely phenomenal experience. From the call the day before to make sure I had everything needed to the friendly service- will be coming back plenty!
NV
Nivaa
22ft Sea Fox 226 Commander for Family fun or Fishing!
Highly recommend Braxton for charter rentals.. excellent service and we had a great time with him
Tristan
22ft Sea Fox 226 Commander for Family fun or Fishing!
Braxton Why Knott Exclusive Rentals is super awesome and a class act. Everything went great- we snorkelled the reefs he recommended at chicken and hen and saw dolphins on our ride. Smooth and flawless, highly recommended . Check out their website for all the cool spear fishing trips they do!
Nicole
22ft Sea Fox 226 Commander for Family fun or Fishing!
Everything about our experience was absolutely stellar from start to finish. The boat was fantastic, Braxton was extremely helpful not only educating on the boat itself but provided great information on routes & places to visit. We had a wonderful day snorkeling the lighthouse and hanging out at Islamorada Sandbar. We will definitely book this again on our next trip to the Keys.
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.
Top Sailboat Rental Locations in the United States
Los Angeles, California
375 boats to rent
Miami, Florida
947 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
136 boats to rent
Honolulu, Hawaii
56 boats to rent
Oakland, California
42 boats to rent
New York, New York
86 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
102 boats to rent
Charleston, South Carolina
121 boats to rent
Newport Beach, California
133 boats to rent
Baltimore, Maryland
44 boats to rent
Long Beach, California
83 boats to rent
Chicago, Illinois
282 boats to rent
Hitchcock, Texas
56 boats to rent
Texas City, Texas
38 boats to rent
Dania Beach, Florida
258 boats to rent
Palm Beach, Florida
143 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!
Dive into Our Journal
February 21, 2024
Data Report: The Top 10 Boating Cities in Florida (Updated for 2025)
Read Article
September 05, 2023
The Ultimate Guide to Weekend Yacht Cruises from Miami
Read Article
March 24, 2020
Florida Keys Boating Guide - Getmyboat
Read Article
December 30, 2019
Miami Boating Guide - Getmyboat
Read Article
August 01, 2023
10 Boating Adventures of a Lifetime
Read Article
October 03, 2022
Getmyboat's Guides to the World of Boating
Read Article
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
