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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
$195/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
$600+/hour
Sunset Cruise on Luxury Sailing Yacht in Waikiki
Sailing in Honolulu · 6 guests

Sunset Cruise on Luxury Sailing Yacht in Waikiki

5.0
$250/hour
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

5.0
$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
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
Enjoy Oahu’s south shore and Waikiki on Rubicon, a beautiful 45’ private yacht
Events in Honolulu · 6 guests

Enjoy Oahu’s south shore and Waikiki on Rubicon, a beautiful 45’ private yacht

5.0
$500/hour
Private Friday Night Sunset & Fireworks - BYOB
Tours in Honolulu · 6 guests

Private Friday Night Sunset & Fireworks - BYOB

3.7
$235/hour
Instant Book
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
Private day, Sunset, Fireworks cruises in Honolulu
Tours in Honolulu · 6 guests

Private day, Sunset, Fireworks cruises in Honolulu

5.0
$120/hour
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
 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
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

Kailua Reviews

  1. 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!

  2. AK

    Alex

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

    We had the absolute best time on our cruise—everything was truly perfect from start to finish. The crew went above and beyond to make the experience memorable, and the entire outing was seamless. We could not have asked for anything better. Thank you so much for an unforgettable day!

  3. SJ

    Sonny

    Private Luxury Tour on 47ft Cranchi Mediterranee

    Epic trip. Super professional and fun crew under Captain Chris. A great captain who always found the smoothest lines through the swell. We had such a great day and even got to share it with a pod of dolphins. Amazing experience, thank you guys.

  4. MB

    Malia

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

    We had Captain Joseph and Kenny as our crew. Both were super attentive and entertaining to talk to. Had smooth sailing and was able to anchor down wherever when my friends and I wanted to swim/snorkel. Will definitely book when I’m in Oahu again! Mahalo!

  5. Nikita

    Nikita

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

    I booked with Captain Rob as a surprise for my sister to ask her to be my MOH and Captain Rob made the experience beyond amazing. He went out of his way to get flowers as I had requested. The whole sailing experience was incredible and felt right out of a movie.

  6. SH

    Sue

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

    What a great evening we had on the water, enjoying the views of Waikiki, Diamond Head, and the gorgeous sunset with Tony! Tony is a real interesting guy, with lots of stories from his vast experiences sailing all over the world. He is passionate about Hawaii and we thoroughly enjoyed chatting with him as we sailed. We are definitely glad that we chose Tony for this sunset cruise. I'm convinced it was the best choice we could have made.