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Kailua, Hawaii Boat Rentals

Page 1 of 124 listings

Have fun in the sun on an extremely comfy pontoon!
Powerboats in Honolulu · 10 guests

Have fun in the sun on an extremely comfy pontoon!

5.0
Snoozed - Active 02 Jan 2026
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
Instant Book
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
Waikīkī’s Premier Catamaran Experience
Sailing in Honolulu · 12 guests

Waikīkī’s Premier Catamaran Experience

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
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

New
$165/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
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
$1,200/hour
Instant Book
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
Best of 2025
$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
Oahu Private Yacht Charters
Events in Honolulu · 6 guests

Oahu Private Yacht Charters

5.0
$550/hour
Special Price: Private Charter - Snorkel, Dolphins, Sunset, Fireworks
Tours in Honolulu · 6 guests

Special Price: Private Charter - Snorkel, Dolphins, Sunset, Fireworks

5.0
$185+/hour
Instant Book
Private Friday Night Sunset & Fireworks - BYOB
Tours in Honolulu · 6 guests

Private Friday Night Sunset & Fireworks - BYOB

5.0
$235/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 2025
$400/hour
Private Adventure Tour with Snorkeling
Powerboats in Honolulu · 6 guests

Private Adventure Tour with Snorkeling

5.0
$275/hour
Private Tour and Snorkeling on the fastest boat in Waikiki!
Powerboats in Honolulu · 12 guests

Private Tour and Snorkeling on the fastest boat in Waikiki!

5.0
$495/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! 🥇

4.4
Superowner
$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!

4.9
Superowner
$185/hour
Instant Book
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
$185/hour

Top Destinations Nearby

Kailua Reviews

  1. CS

    Chris

    Special Price: Private Charter - Snorkel, Dolphins, Sunset, Fireworks

    From start to finish Kelly was amazing! Communication was fast and she did everything to make my 4th of July experience truly unforgettable. Kelly gave great directions in location the pier and met me at the front to walk us to her boat. 5 stars all around!!!

  2. Douglas

    Douglas

    Private Luxury Tour on 47ft Cranchi Mediterranee

    Thank you to Capt Flo and her crew for the outstanding job they did taking care of family today. They did everything possible to make sure that we were comfortable and enjoying ourselves. Capt Flo did her best to keep the boat in better waters to minimize the roughness of the open ocean. Highly recommend booking with this company. They will take great care of you and make sure that you have an enjoyable experience.

  3. Rob

    Rob

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

    Excellent experience for our whole family. Would definitely recommend. Tony was fun and helpful. It was the first time for many of us and Tony did an excellent job of making our family feel welcome. We had an amazing time sailing, snorkeling, and sunbathing. Four hours just flew by!

  4. CJ

    Casey

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

    We booked Captain Rob's sunset sail so that we could watch the fireworks from the ocean and it was such an amazing experience! Captain Rob and his crew were extremely helpful, kind, and made us all feel welcome from the second we stepped onto the boat. Would 10000% recommend this trip to anyone thinking about booking -- it was one of our favorite things we did during our visit!

  5. AS

    Audrey

    Special Price: Private Charter - Snorkel, Dolphins, Sunset, Fireworks

    Had the most perfect day on the most perfect boat with the most perfect team. Care and Kelly went out of their way to make sure we had literally everything we needed to celebrate my 54th birthday in style! They went out of their way to tailor the itinerary to give us the perfect day on the water. It was the best way I could have dreamed of and I enjoyed every second of it. It truly felt like we were on a friend’s boat - only we were pampered. The boat was spotless and the equipment was too. Highly recommend this for anyone looking for a fun day out on the ocean! Thank you so much!

  6. AN

    Amy

    Private Friday Night Sunset & Fireworks - BYOB

    Parking is very difficult on Friday evening but Kelly and Care were super helpful with directions and even gave us our full two hours because it took us long to find parking. Super enjoyable and fun!