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The Best Sailboat Rentals Near Osprey
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Osprey
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$260-$1,540
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$565
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$70-$290
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$265
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$50-$270
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$90-$100
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$1,690
Rafting
A high-energy adventure for the whole family
$120
Kayaks
Who says you need a motor to have fun on the water?
$120
Recent Reviews in Osprey
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.
TN
TUNG
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Definitely recommend. We showed up almost an hour late because we ended up going to wrong Marina and he still waited for us and was not mad at us for having him wait. He explained how to operate and was there to assist us when we came back to Marina to help us dock. Super nice gentleman and will definitely book again.
Lesley
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Our experience renting from Meghan was excellent! The boat was great; clean and delivered on time with a full tank of gas. Meghan responded quickly to our initial request and communication was great throughout. We would definitely rent again from Meghan.
Christopher
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Thanks again to Meghan and Martin for making our boat rental experience amazing from start to finish. The new boat was awesome and everything went exactly as planned. We will be using them again in the future and recommend them for a top notch experience as well.
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!
Real reviews from happy Getmyboaters.
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