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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 234 listings

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
 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🥇!

5.0
Superowner
$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
$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
$185/hour
Instant Book
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
$299/hour
Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇
Sailing in Honolulu · 12 guests

Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇

4.9
Superowner
$185/hour
Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!

4.9
$175/hour
Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 30 guests

Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii

5.0
$650/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! 🥇

4.3
Superowner
$185/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
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

New
$165/hour
42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.
Sailing in Honolulu · 6 guests

42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.

5.0
$235/hour
ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki
Sailing in Honolulu · 6 guests

ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki

4.9
$200/hour
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$165/hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500+/hour
41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa
Sailing in Haleiwa · 6 guests

41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa

5.0
$250+/hour
Private Luxury Charter in Honolulu on a 41' Japanese Sloop
Sailing in Honolulu · 6 guests

Private Luxury Charter in Honolulu on a 41' Japanese Sloop

New
$233+/hour
46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii
Sailing in Kapolei · 6 guests

46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii

5.0
$700/hour
Stunning Beneteau 42 Experience in Honolulu, Oahu
Sailing in Honolulu · 6 guests

Stunning Beneteau 42 Experience in Honolulu, Oahu

4.0
$1,550/day
50ft Hans Christian Yacht
Sailing in Honolulu · 6 guests

50ft Hans Christian Yacht

New
$199/hour
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$1,500/hour
Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)
Sailing in Honolulu · 10 guests

Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)

New
$4,500/day
Honolulu Private Sunset Sail
Sailing in Honolulu · 49 guests

Honolulu Private Sunset Sail

New
$1,800/hour
Personalized Private Charters on 37 passenger Sailing Catamaran in Waikiki
Sailing in Honolulu · 37 guests

Personalized Private Charters on 37 passenger Sailing Catamaran in Waikiki

New
$700/hour

Top Destinations Nearby

Sailing Reviews in O‘ahu

  1. Ages

    Ages

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

    So amazing! Loved it so much, it was so beautiful, so peaceful and great to have the boat just for my husband and I. The most beautiful way to enjoy a sunset. Truly so romantic. Fellas I’m telling you, it’s worth it to splurge to be able to have your own boat for you and your significant other. Will definitely be booking again and will recommend to all of our friends who are visiting Oahu.

  2. KG

    Katy

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

    What a WONDERFUL day! The snorkeling was even better because Savannah and Whitney had us buttoned up on exactly how to see the best spots. Our Captain, Tom was the perfect blend with Savannah and Whitney. The boat was perfect for all of us. We were very comfortable with 10 people. I highly recommend both the boat AND the crew!

  3. TF

    Teresa

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

    This was the best charger we have been on! The staff were exceptional and the boat was fantastic! We had such a great time! Thank you, Bella, Savannah, and CPT George!

  4. RW

    Rachel

    Epic 34' Catamaran Sailing in Waikiki

    Our trip with captain Polu was so much fun! Super easy to communicate and book. Lots of room on boat, clean, and he was very flexible with where we wanted to go and what we wanted to do. He provided an ice chest, snorkel equipment, floaties, and a speaker!

  5. KD

    Keani

    Epic 34' Catamaran Sailing in Waikiki

    Captain Polu was AMAZING! He has great response time and was very accommodating to our needs. Very kind and made us feel very comfortable. Thank you again Captain Polu!

  6. JA

    Julian

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

    Tony was great host and whoever is seeing this post I highly recommend you book with this captain. Friendly and very informative especially when we were looking for whales. The boat was clean and comfortably fit the 5 of us. Tony provided the snorkeling equipment as well and took us to a great snorkeling site to view the fishes which my kids enjoyed. I highly recommend this captain for your next aloha adventure!