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The Best Sailboat Rentals in 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
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$35-$650
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$40-$250
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$190-$815
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$330
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$75-$335
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$110-$265
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$300-$920
Kayaks
Who says you need a motor to have fun on the water?
$65-$320
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$120-$145
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$125-$150
Top Sailboat Rental Locations Near Madeira Beach
Bay Pines, Florida
9 boats to rent
Treasure Island, Florida
152 boats to rent
Seminole, Florida
25 boats to rent
Saint Pete Beach, Florida
38 boats to rent
Gulfport, Florida
24 boats to rent
Largo, Florida
29 boats to rent
Tierra Verde, Florida
87 boats to rent
Saint Petersburg, Florida
258 boats to rent
Clearwater, Florida
244 boats to rent
Dunedin, Florida
18 boats to rent
Tampa Bay, Florida
240 boats to rent
Anna Maria, Florida
7 boats to rent
Palm Harbor, Florida
8 boats to rent
Anna Maria Island, Florida
55 boats to rent
Holmes Beach, Florida
34 boats to rent
Lake Tarpon, Florida
7 boats to rent
Tampa, Florida
391 boats to rent
Bradenton Beach, Florida
7 boats to rent
Recent Reviews in Madeira Beach
Taylor
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Rented this boat for my best friend’s bachelorette and everything was perfect. Everything was true to the images and the captain and crew were awesome. Would absolutely recommend and would book again.
PA
Poorna
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
We had an amazing time on the pontoon boat, and it was a perfect experience for our family. The boat was clean, comfortable, and very well maintained. Richard was extremely friendly and took the time to explain everything clearly about the boat and the surroundings, which made us feel confident and relaxed. Life vests were available for everyone, which was especially reassuring for families with kids. The ride was smooth, enjoyable, and safe, allowing us to fully enjoy our time together. Overall, it was a fantastic family experience, and we truly appreciated Richard’s professionalism and kindness. Highly recommended for families looking for a fun and stress-free outing on the water!
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!
Zach
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Could not recommend this vessel and crew more. We rented it for the 4th of July and it was an unforgettable experience for our group. Despite some shaky weather we still had a blast. The boat is incredible and such a fair rate compared to other similar listings. Captain Dave and Joe were AWESOME. Would book again in a heartbeat!
Deja
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!
Top Sailboat Rental Locations in the United States
Los Angeles, California
366 boats to rent
San Francisco, California
80 boats to rent
Miami, Florida
1085 boats to rent
Oakland, California
47 boats to rent
Marina del Rey, California
131 boats to rent
San Diego, California
108 boats to rent
Honolulu, Hawaii
41 boats to rent
New York, New York
78 boats to rent
Annapolis, Maryland
52 boats to rent
Chicago, Illinois
285 boats to rent
Fort Lauderdale, Florida
253 boats to rent
Charleston, South Carolina
126 boats to rent
Hitchcock, Texas
50 boats to rent
Texas City, Texas
41 boats to rent
Dania Beach, Florida
230 boats to rent
Baltimore, Maryland
50 boats to rent
Houston, Texas
48 boats to rent
Kemah, Texas
40 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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