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Fishing Charters
Let a captain do the driving while you do the fishing
$65-$1,870
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$1,940
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$135-$1,120
Kayaks
Who says you need a motor to have fun on the water?
$50-$930
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$65-$320
Sailboats
Set sail with these traditional wind-powered boats
$160-$475
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$150-$225
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$125-$170
Diving
Explore the ocean depths with trained boat operators
$75
Christi
New 21.2 Sportsman Boat perfect size for the Keys
Beautiful boat that performed well for our needs in Key Largo! Great communication! Thank you!
Mark
Luxury Adventure Boat: Brabus of the Seas - Up to 13ppl - Islamorada/Key Largo
What a great experience and very easy to book online! We did a boat rental for a bachelor party and was perfect to head out on the water, go wherever we wanted. We chose to go to a sandbar, some mangrove areas, then stopped for lunch at hurricane hole. Very easy communication and JP will help with booking your captain. Boat was extremely nice and modern, clean, and plenty of space to spread out. Overall a great memorable experience. Thank you!
GT
Greg
Jeanneau NC 895 Luxury Yacht - Private Key West Boat Charter
David was a great host. No surprise charges and very accommodating in all aspects. Captain Dustin and Christina were very knowledgeable on local spots to avoid the wind and were great to hang out with for the day. We would highly recommend spending a day touring with them.
MH
Missy
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Couldn’t have asked for a better 40th birthday! Anthony helped us decided on the best spots for what we wanted to do. Mystic the pug was a welcome bonus. The most amazing and unexpected part was the incredible drone footage of our party enjoying the water that Anthony shot and shared with us. Definitely book with Anthony!
JI
John
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Great time out with Anthony. He suggested a nice itinerary based on what we wanted to see. He very patiently taught my 13 year old son how to wake skate. Probably the highlight of his trip. Overall, couldn’t have asked for a better captain. We had a blast and hope to do it again.
LL
Lauren
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Our trip was amazing!! I went with 3 other friends and the trip was perfect! Would highly recommend to anyone looking for a day out on a boat in key west! We loved going to the sand bars and floating. Will definitely books again next time we are back!
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!