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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 124 listings

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

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
$299/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
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 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
Best of 2026
$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! 🥇

4.5
Superowner
Best of 2026
$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
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

5.0
$165/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
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
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$232/hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$332/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
$300/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
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
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
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$900/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
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
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 Reviews in O‘ahu

  1. PS

    Paul

    Epic 34' Catamaran Sailing in Waikiki

    Had an amazing time with Captain Polu on a 4-hour trip around Oahu! We started with some snorkeling, enjoyed a beautiful sail along the coastline, then returned to our first snorkel spot and got to see sea turtles. We finished the day with a picturesque sunset. It was the perfect trip! Captain Polu was super chill, accommodating, and asked us what we wanted to do. He was well prepared and had all the snorkeling gear ready for us. Highly recommend Captain Polu to anyone looking for a fun, relaxing, and memorable day on the water.

  2. SR

    Steve

    Epic 34' Catamaran Sailing in Waikiki

    Amazing trip! We are a family of eight and had the best day ever. The boat is great condition and the itinerary was great. We could spend as much time as we wanted snorkeling and swimming. Great day! We loved looking at all the other boats with a million people on them while on our own private boat day!

  3. JD

    Jean Sebastien

    Epic 34' Catamaran Sailing in Waikiki

    ⭐⭐⭐⭐⭐ We had an absolutely amazing day! Captain Polu was fantastic from start to finish. He was incredibly friendly, welcoming, and made us feel comfortable the entire time. Communication before the trip was excellent, meeting him was easy, and everything was exactly as promised. The catamaran was beautiful, and he made our day truly memorable. We couldn’t have asked for a better experience. We highly recommend Captain Polu and would definitely book with him again next time we’re in Hawaii. Thank you for an unforgettable day!

  4. MY

    Matthew

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

    Great experience with the crew! They were very attentive and helpful. Great time snorkeling and saw a lot of interesting fish and turtles. Everyone had a great time! Would highly recommend booking again with them

  5. HS

    Heather

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

    We had a fantastic day sailing with Seas the Day with Captain Joseph and Kenny with 2 families. Plenty of time to sail, swim and snorkel and saw lots of dolphins and even a sea turtle along the Waikiki coast. Highly recommend them!

  6. AG

    Ana

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

    We had an amazing experience with Tony! He was friendly, professional, and made sure everyone felt welcome and comfortable throughout the trip. The boat was clean and well-maintained, and everything was exactly as described. We had a fantastic time on the water and truly appreciated Tony's hospitality and attention to detail. I would highly recommend booking with him if you're looking for a fun, relaxing, and memorable boating experience. Thank you, Tony!