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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 230 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🥇!

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
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
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
$299/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 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
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
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
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, trimaran swimming & sailing charter experience in Waikiki
Sailing in Honolulu · 6 guests

ONE OF A KIND, trimaran swimming & sailing charter experience in Waikiki

4.9
$250/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
Sunset Cruise on Luxury Sailing Yacht in Waikiki
Sailing in Honolulu · 6 guests

Sunset Cruise on Luxury Sailing Yacht in Waikiki

5.0
$550/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
BYOB Private Waikīkī Catamaran Charters
Sailing in Honolulu · 35 guests

BYOB Private Waikīkī Catamaran Charters

5.0
$600+/hour
Largest, most luxurious sailing catamaran on the island of Oahu
Events in Honolulu · 12 guests

Largest, most luxurious sailing catamaran on the island of Oahu

5.0
$1,119+/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
Adventures aboard 48' Luxury Catamaran
Sailing in Waianae · 12 guests

Adventures aboard 48' Luxury Catamaran

5.0
$700/hour
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

New
$165/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
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$900/hour
Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)
Sailing in Honolulu · 12 guests

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

New
$660/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

Sailing Reviews in O‘ahu

  1. 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.

  2. Nicole

    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!

  3. Zoie

    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!

  4. 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.

  5. MH

    Meg

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

    Fantastic value, we spent 3 hours on Tony’s boat with 6 of us. Most beautiful day, Tony gave us an incredible experience with swimming stops and easy cruising. We will definitely do it again!

  6. BP

    Benedict

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

    Captain Joseph was incredibly laid-back and our group had really fun conversations with him throughout the entire trip. He was super communicative to our group at the start and continued to do so throughout. Boat size was good for our group of 10 and AMAZING sunset and city views!! Unforgettable experience