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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
$115-$1,195
Fishing Charters
Let a captain do the driving while you do the fishing
$45-$430
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$45-$445
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$425
Sailboats
Set sail with these traditional wind-powered boats
$30-$1,060
Kayaks
Who says you need a motor to have fun on the water?
$10-$455
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-$285
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Paulius
Family Friendly 21' Sea Fox CC - Cruising/Fishing in Bradenton, Florida
I would recommend this service to ever as it was superb service from the day of booking until we finished our trip. Winston have replied to every single our message and provided good service!!! Well done!! I would say you won’t be disappointed with the service Winston has. !!!
BA
Bria
Island Hop to Egmont Island and Passage Key...Dolphin Tour...Luxury Powerboat
This was the best experience ever! Do not hesitate to book this trip! The views are worth it, the captain is AMAZING, Ryan is the best he answers any and all of your questions in a timely manor. This trip is perfect for couples or groups. 10/10 !
MM
Minette
20' Bennington pontoon, Yamaha 70HP, up to 9 people - gas included! Bay Pines
Great area to boat around - even saw some dolphins! Hosts were excellent with great communication. Thank you for a great ending to our trip!
RR
Robert
Nitro Z18 175HP Bass Boat in Lake Tarpon
Amazing boat, performs like a dream! And, it comes kitted out with EVERYTHING you need for a successful day of fishing on the water. Plus, Mike is super accommodating and helpful, he gave us full lessons on how to operate everything and local advice that beat out everything we read online!
Brian
Family Friendly 21' Sea Fox CC - Cruising/Fishing in Bradenton, Florida
Winston exceeded our expectations from pick up to drop off. His communication was excellent, the boat was in great working order and everything was perfect for our day on the water. I 100% recommend renting from Winston. Thank you Winston!
JL
Jonathan
Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now
Lisa and Bruce were great hosts. They took time before we shoved off to familiarize us with the boat, equipment and local waterways. The boat is nice, no issues. Overall we had a good day on water. Thanks!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
April 17, 2024
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December 30, 2019
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September 13, 2023
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August 21, 2023
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August 03, 2023
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June 02, 2023
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