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The Best Sailboat Rentals Near Kailua
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Kailua
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$185-$1,150
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$155-$675
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$130-$500
Fishing Charters
Let a captain do the driving while you do the fishing
$170-$380
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$175-$385
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$400
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150
Top Sailboat Rental Locations Near Kailua
Honolulu, Hawaii
52 boats to rent
O‘ahu, Hawaii
70 boats to rent
Maui, Hawaii
8 boats to rent
Kalaoa, Hawaii
8 boats to rent
Kailua-Kona, Hawaii
8 boats to rent
Sausalito, California
15 boats to rent
San Francisco, California
75 boats to rent
Tiburon, California
16 boats to rent
Oakland, California
43 boats to rent
Alameda, California
21 boats to rent
Sacramento, California
31 boats to rent
Redding, California
11 boats to rent
Shasta Lake, California
11 boats to rent
Arden-Arcade, California
27 boats to rent
Folsom, California
13 boats to rent
Granite Bay, California
7 boats to rent
Folsom Lake, California
27 boats to rent
El Dorado Hills, California
18 boats to rent
Recent Reviews in Kailua
Cole
A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!
Absolutely phenomenal experience. The captain ran a tight, professional operation while keeping the energy high and the vibe relaxed. From departure to docking, everything was smooth, well-coordinated, and clearly delivered by someone who knows the water and knows how to host. The route was stunning, captain made everyone on board feel taken care of. If you’re looking for a tour that overdelivers on value, atmosphere, and overall execution, this is it. Five stars. would book again without hesitation.
SH
Steven
Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!
We had an unforgettable evening aboard this private yacht with Captain Joseph and Kenny. They brought us to the perfect spot at sunset, where we were able to honor my mom with a celebration of life and scatter her ashes in a peaceful, beautiful setting. Their professionalism, kindness, and attention to detail made the moment seamless and meaningful. The evening ended with fireworks over the water — a breathtaking finale to a day filled with love and remembrance. This was more than just a yacht trip; it was an experience we’ll cherish forever. Thank you, Captain Joseph and Kenny, for making it extraordinary.
Nicole
Epic 34' Catamaran Sailing in Waikiki
Captain Polu was amazing! I was over eager to get in the water and jumped in before I should have, oops. He was patient and polite and took us to some of the best spots. We will definitely book with him again. Thank you for such a memorable experience!
Zoie
Epic 34' Catamaran Sailing in Waikiki
Captain Polu gave our group of 11 the experience of a lifetime with this boat! We loved snorkeling and swimming and we even saw dolphins!! The boat had everything we needed and had a great amount of space to chill in front and at the table. Would totally come back again!
Davin
Epic 34' Catamaran Sailing in Waikiki
Fantastic trip ! Huge and nice boat , perfect for a group and plenty of places to lay out . Had fun swimming and snorkeling. Excellent captain. We felt very cared for. Already planning next year
KL
Katheryne
A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!
Captain Rob was helpful answering all my questions. Captain Joseph and Kenny were very kind and empathetic. We booked the trip to spread our mom's ashes, and they were so respectful and kind. They even gave us a few laughs during a difficult time. They also gave us free water bottles. We really appreciated them! <3 Thanks you guys.
Top Sailboat Rental Locations in the United States
Los Angeles, California
374 boats to rent
Miami, Florida
956 boats to rent
Marina del Rey, California
136 boats to rent
San Francisco, California
75 boats to rent
Oakland, California
43 boats to rent
Honolulu, Hawaii
52 boats to rent
New York, New York
86 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
101 boats to rent
Charleston, South Carolina
121 boats to rent
Newport Beach, California
131 boats to rent
Long Beach, California
84 boats to rent
Baltimore, Maryland
44 boats to rent
Chicago, Illinois
281 boats to rent
Hitchcock, Texas
56 boats to rent
Texas City, Texas
38 boats to rent
Dania Beach, Florida
258 boats to rent
Noyack, New York
46 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!
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
