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The Best Sailboat Rentals Near Madeira Beach
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Madeira Beach
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$450
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$125-$1,195
Fishing Charters
Let a captain do the driving while you do the fishing
$30-$430
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$40-$465
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$50-$410
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$375
Kayaks
Who says you need a motor to have fun on the water?
$15-$505
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$85-$1,200
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$110-$315
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110-$275
Top Sailboat Rental Locations Near Madeira Beach
Recent Reviews in Madeira Beach
PS
Paige
Cabbage Key, Captiva Day Trip 1-6 people Captained
Wonderful trip. Made for the perfect afternoon activity for three couples of varying ages, smooth ride and a great value for seeing the views around the fort myers/Cape Coral area. Joe was extremely responsive and prompt to any questions/requests and made sure we were comfortable throughout our travels. Would recommend to anyone!
Andrea
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
I went out with Nick for my bachelorette. We had the most amazing time. It was so beautiful, smooth and relaxing. Highly recommend to anyone
Aleczander
50ft Catamaran Charter with Water Toys - Deerfield/Boca Raton, FL
Proposed to my girlfriend of 7 years and couldn’t have asked for a better charter. We will be back soon.
CC
Christine
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Richard was prompt and affordable. We really enjoyed our day out. There should be mention of the wear and tear on the boat and the fact that the depth finder was broken. Kind of an issue when navigation in such shallow water. Luckily we have experience with that but those who do not may have an issue.
CB
Christine
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Great value and very efficient communication. The day we rented a boat was very windy. Richard provided a pontoon with a higher horsepower motor - it made our day much more enjoyable. We will definitely reach out to rent from Richard next time we are in FLA!
LS
Leighanna
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
My family and I had a blast! we celebrated my birthday and this was an awesome time. Richard was quick to respond, fantastic price point, made drop off and pick up so easy, and all around amazing great guy. Don't hesitate to book as you will be thrilled that you did! **Remember an aux cord to hook up your device to listen to music**
Top Sailboat Rental Locations in the United States
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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