By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$375
Sailboats
Set sail with these traditional wind-powered boats
$375-$500
Fishing Charters
Let a captain do the driving while you do the fishing
$300-$400
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$375

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!
JD
Jepera
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
This was an amazing experience. Mr. Israel was awesome and made us feel very comfortable. His hospitality was great. I will definitely be back. The boat was perfect for my birthday.

elizabeth
Enjoy Cancun in 32ft Wellcraft for 6 people!
Edgar estuvo atento desde el día uno de la reserva, ofrece toda la actitud y disposición para un viaje súper divertido. Sus amenidades están increíbles. Nos encantó y definitivamente reservaríamos siempre con él.
LQ
Laura
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
We had an absolute blast! Would recommend to anyone! Darren and Israel were so much fun they celebrated our birthday event with us and even decorated the boat for us. They let us play our music and bring food. We snorkeled and they took amazing pictures for us. Book now!

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.
SO
Stephen
31ft SeaRay Sundancer Luxury Boat Chartering in Grand Cayman
This was the highlight of our trip. Captain Bryan and his first mate Ryan were fantastic. They took us to all the places we wanted and were very easy going. They knew a great detail about every stop and spun some history and facts about the area. We’d use them again for sure!
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!

September 13, 2023
Read Article

August 21, 2023
Read Article

August 03, 2023
Read Article

June 02, 2023
Read Article

August 31, 2022
Read Article

December 30, 2019
Read Article