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The Best Sailboat Rentals Near the Cayman Islands
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in the Cayman Islands
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$1,000
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$300
Fishing Charters
Let a captain do the driving while you do the fishing
$300
Top Sailboat Rental Locations Near the Cayman Islands
Recent Reviews in the Cayman Islands
Jaela
46 feet luxury yacht in Montego Bay with round trip transportation!
Booked KnotStressin’ for my 30th birthday weekend in Jamaica. We had a great time on the boat. We got to do the jet car, which was a BLAST. We got plenty of photos & videos. The drinks continuously flowed the whole time on the boat. Captain Milky, Host Tamara & Kamoya, lifeguard Shane were absolutely amazing! They were considerate, kind, respectful, very very welcoming! My friend, family, & I had a wonderful time. I want to book with them each time I come back! 🫶🏾🤍 I love y’all! Thank yall for making 30 everything I wanted & more! 🫶🏾
CC
Cristi
Sail away in Montego Bay! 39ft Leopard Catamaran
This was the best part of our trip! The boat was clean, safe and a lot of fun. Hugh thanks to the Capt and the crew! Working with Stacey was great. I would highly recommend her boat to anyone visiting!
NR
Nykeema
46 feet luxury yacht in Montego Bay with round trip transportation!
I had an amazing time! Everyone was so nice! Tamara was so kind and caring, snoop never left us hanging and made sure we were good a s Bobby was the best captain. The food was great and even my vegan guest had options.
Kim
46 feet luxury yacht in Montego Bay with round trip transportation!
Top tier! The professionalism started from the time of inquiry. The booking was easy and Dedrick was responsive and met all of my expectations. Definitely recommending to all of my friends in the states.
SC
Sharifa
46 feet luxury yacht in Montego Bay with round trip transportation!
Thank you! 🙏🏾 lm had an amazing time for my birthday! Myself and my guests had a great time! Thank you for making my birthday so special !
SG
Sheena
46 feet luxury yacht in Montego Bay with round trip transportation!
Just Book it!! Amazing Experience!!
Top Sailboat Rental Locations in the Cayman Islands
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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