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The Best Boat Rentals Near Big Pine Key
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Big Pine Key
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$240-$1,030
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$870
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$700
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$700
Sailboats
Set sail with these traditional wind-powered boats
$200-$600
Kayaks
Who says you need a motor to have fun on the water?
$130-$170
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$125
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$130-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$135
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$850
Top Boat Rental Locations Near Big Pine Key
Florida Keys, Florida
104 boats to rent
Marathon, Florida
22 boats to rent
Stock Island, Florida
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Key West, Florida
39 boats to rent
Islamorada, Florida
25 boats to rent
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15 boats to rent
Key Largo, Florida
24 boats to rent
North Key Largo, Florida
21 boats to rent
Marco Island, Florida
32 boats to rent
Coral Gables, Florida
44 boats to rent
Key Biscayne, Florida
9 boats to rent
Miami, Florida
912 boats to rent
Naples, Florida
62 boats to rent
Miami Beach, Florida
389 boats to rent
North Bay Village, Florida
54 boats to rent
North Miami, Florida
183 boats to rent
North Naples, Florida
20 boats to rent
North Miami Beach, Florida
43 boats to rent
Recent Reviews in Big Pine Key
Cassadee
Key West Luxury Charters
We had the BEST day out on the water with Captain TJ and Carlos from Reel Paradise Charters! From start to finish, they made the entire experience so fun, smooth, and unforgettable. TJ was absolutely amazing — so knowledgeable, personable, and clearly passionate about what he does. He went above and beyond to make sure everyone was having a great time, and we couldn’t have asked for a better captain. Carlos was equally awesome, super friendly and attentive, and made sure everything ran perfectly. The boat was beautiful, the views were stunning, and the energy the whole day was unmatched. If you’re thinking about booking a boating adventure, I HIGHLY recommend Reel Paradise Charters — you’ll be in the best hands with TJ and Carlos!
GG
Grace
Stylish elegance and spacious comfort ... your best time ever!
Captain Bridget was such a blast!! She was very accommodating to our large group and showed us some awesome spots and a natural lazy river! Can’t wait to book with her again!!
Emery
Stylish elegance and spacious comfort ... your best time ever!
I cannot recommended booking this boat experience for any group. We had the pleasure of having captain Bridget who went above and beyond to ensure our experience was everything and more!
JR
James
Pontoon Boat !! Enjoy Paradise Like A Local!
We had a blast at the sand bar with Capt. Bridget. Great day, awesome, knowledgeable captain with great ideas for our day on the water. Would highly recommend.
RW
Reece
Stylish elegance and spacious comfort ... your best time ever!
Amazing trip! Captain Bridget was the life of the party and took great care of my girls and I for my bachelorette trip! Highly recommend
Tiffany
Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.
David made sure it was a special day for all of us.
Top Boat Rental Locations in the United States
Miami, Florida
914 boats to rent
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422 boats to rent
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391 boats to rent
Los Angeles, California
376 boats to rent
Chicago, Illinois
281 boats to rent
Fort Lauderdale, Florida
269 boats to rent
Hollywood, Florida
262 boats to rent
Saint Petersburg, Florida
261 boats to rent
Dania Beach, Florida
249 boats to rent
Clearwater, Florida
237 boats to rent
North Miami, Florida
183 boats to rent
Austin, Texas
182 boats to rent
Seattle, Washington
155 boats to rent
Madeira Beach, Florida
145 boats to rent
Treasure Island, Florida
139 boats to rent
Marina del Rey, California
137 boats to rent
Newport Beach, California
132 boats to rent
Destin, Florida
130 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!
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Real reviews from happy Getmyboaters.
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