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Kailua, Hawaii Boat Rentals & Yacht Charters

Page 1 of 124 listings

Kaneohe Bay Sandbar - 25 Avalon Pontoon Rental
Powerboats in Pupukea · 12 guests

Kaneohe Bay Sandbar - 25 Avalon Pontoon Rental

5.0
$225/hour
Twin hull powered boat for rent - up to 10 people
Powerboats in Honolulu · 10 guests

Twin hull powered boat for rent - up to 10 people

5.0
$275/hour
Come explore, the uncrowded south east coast of Oahu on your own 30 foot boat
Powerboats in Honolulu · 6 guests

Come explore, the uncrowded south east coast of Oahu on your own 30 foot boat

New
$225/hour
BYOB Private Waikīkī Catamaran Charters
Sailing in Honolulu · 35 guests

BYOB Private Waikīkī Catamaran Charters

5.0
$650+/hour
Sunset Cruise on Luxury Sailing Yacht in Waikiki
Sailing in Honolulu · 6 guests

Sunset Cruise on Luxury Sailing Yacht in Waikiki

5.0
Snoozed - Active 14 Jul 2026
Luxe Catamaran in Waikiki, Hawaii - 43ft Private Catamaran Yacht
Powerboats in Honolulu · 6 guests

Luxe Catamaran in Waikiki, Hawaii - 43ft Private Catamaran Yacht

5.0
$800/hour
Waikiki’s Premier Lagoon 420 Catamaran Experience For 12 Guests
Sailing in Honolulu · 12 guests

Waikiki’s Premier Lagoon 420 Catamaran Experience For 12 Guests

New
$350+/hour
Private Luxury Tour on 47ft Cranchi Mediterranee
Events in Honolulu · 12 guests

Private Luxury Tour on 47ft Cranchi Mediterranee

4.9
$367+/hour
2-Hour Tour - 47ft Cranchi Mediterranee Luxury Yacht Charter in Honolulu
Events in Honolulu · 12 guests

2-Hour Tour - 47ft Cranchi Mediterranee Luxury Yacht Charter in Honolulu

5.0
$450/hour
Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht
Sailing in Honolulu · 6 guests

Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht

New
$1,800/day
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

5.0
$165/hour
Oahu Sunset & City Lights Yacht Cruise – Private 54’ Sunseeker Experience
Events in Honolulu · 8 guests

Oahu Sunset & City Lights Yacht Cruise – Private 54’ Sunseeker Experience

New
Snoozed - Active 02 Sep 2026
24ft Center Console Edgewater Center Console in Honolulu
Powerboats in Honolulu · 6 guests

24ft Center Console Edgewater Center Console in Honolulu

New
$200/hour
Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
Sailing in Honolulu · 6 guests

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

5.0
$180/hour
Private Friday Night Sunset & Fireworks - BYOB
Tours in Honolulu · 6 guests

Private Friday Night Sunset & Fireworks - BYOB

3.7
$235/hour
SPECIAL PRICE: Private Boat - Snorkel, Paddle Board, Scooter, Turtles, Dolphins
Tours in Honolulu · 6 guests

SPECIAL PRICE: Private Boat - Snorkel, Paddle Board, Scooter, Turtles, Dolphins

5.0
$200+/hour
Instant Book
Come and Sail on this Beautiful 50' Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 6 guests

Come and Sail on this Beautiful 50' Catamaran in Honolulu, Hawaii

New
$500/hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 15 guests

Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

5.0
Superowner
Best of 2026
$400/hour
Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

5.0
$700/hour
The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇
Sailing in Honolulu · 12 guests

The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇

4.5
Superowner
Best of 2026
$185/hour
40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu
Sailing in Honolulu · 12 guests

40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

4.8
Superowner
Best of 2026
$185/hour
Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!
Tours in Honolulu · 6 guests

Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

4.8
Superowner
Best of 2026
$185/hour
 A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!
Sailing in Honolulu · 12 guests

A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

4.8
Superowner
Best of 2026
$185/hour
Waikiki Private Boat Adventure (45 ppl): Explore the ocean with the best crew!
Events in Honolulu · 45 guests

Waikiki Private Boat Adventure (45 ppl): Explore the ocean with the best crew!

5.0
$500+/hour

Kailua Reviews

  1. Brittany

    Brittany

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    This boat was beautiful and the staff were amazing! They were quick to show us any nearby sea life and educate us about it as well. The boat was equipped with many different amenities and gear. The best thing about renting this boat, is if you do the math, you’re spending less than you would on a tour and you get to do the same thing you would do on a tour. The difference is you get to do it privately just with your family and friends and not with a whole bunch of strangers. This was the highlight of our trip!

  2. KA

    Kelsey

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    Ashliey and her team were so efficient! They truly made this trip special by going out of their way to make sure all our needs are met. Truly above and beyond service with the most memorable experience, I hope to book this catamaran next time we are on Oahu! We will be back.

  3. NJ

    Nichole

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    Omg! We loved the catamaran! The crew was totally cool and there were no delays!! A huge value for those that want privacy and a great experience!!!

  4. AW

    Asiah

    Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

    Our staff was amazing Kenny and Captain R was so accommodating and so proactive with our booking. We really enjoyed ourselves ☺️ thank you for helping make our Hawaii trip even better!

  5. Dd

    Danielle

    SPECIAL PRICE: Private Boat - Snorkel, Paddle Board, Scooter, Turtles, Dolphins

    10/10 star experience!!!! ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ We had an absolutely incredible experience with Captain Kelly and Care — truly one of the highlights of our entire trip! From the moment we stepped on the boat, everything was top-notch. The boat itself was spotless, beautifully maintained, and so comfortable. You can tell they genuinely care about creating an amazing experience for their guests. They had everything we could possibly need ready for us — paddle boards, snorkel gear, even an underwater scooter which made exploring the water so much fun. They also had waters and snacks available throughout the trip, which was such a thoughtful touch and made the whole experience feel even more elevated and relaxing. Captain Kelly and Care make such an amazing team. They were friendly, welcoming, knowledgeable, and made the entire day seamless and unforgettable. We truly could not have asked for a better experience and will 100% be booking with them again the next time we’re back. Highly, highly recommend!

  6. Jessi

    Jessi

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    We had an amazing time on the catamaran! The crew were very attentive and kind! Will definitely try to use them again if we are back on the island.