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Kailua, Hawaii Boat Rentals

Page 1 of 124 listings

Marina Paradise, 24' Hurricane Deck Boat, 10 People, China Walls!
Powerboats in Honolulu · 10 guests

Marina Paradise, 24' Hurricane Deck Boat, 10 People, China Walls!

4.8
$190/hour
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
$150/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
Kaneohe Bay Coral Reef Self-Guided Kayaking Adventure
Adventures in Pupukea · 2 guests

Kaneohe Bay Coral Reef Self-Guided Kayaking Adventure

New
$246/hour
Amazing Kaneohe Bay Sandbar Self-Guided Kayak Experience
Adventures in Pupukea · 2 guests

Amazing Kaneohe Bay Sandbar Self-Guided Kayak Experience

New
$384/hour
Robalo R272 Luxury Fishing and Snorkel Powerboat in Honolulu, Hawaii
Powerboats in Honolulu · 8 guests

Robalo R272 Luxury Fishing and Snorkel Powerboat in Honolulu, Hawaii

5.0
$500/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
Cranchi Mediterranee 47HT Luxury Power Yacht Charter in Honolulu, Hawaii
Tours in Honolulu · 12 guests

Cranchi Mediterranee 47HT Luxury Power Yacht Charter in Honolulu, Hawaii

5.0
$333+/hour
Best Waikiki Private Guided Snorkel Charter on Oahu
Tours in Honolulu · 6 guests

Best Waikiki Private Guided Snorkel Charter on Oahu

New
$325/hour
Best Waikiki Private Charter - Snorkel, Dive and Sunset Cruises!!
Powerboats in Honolulu · 6 guests

Best Waikiki Private Charter - Snorkel, Dive and Sunset Cruises!!

New
$325/hour
Waikiki's Favorite Island Time Private Yacht Charter
Events in Honolulu · 6 guests

Waikiki's Favorite Island Time Private Yacht Charter

New
$315+/hour
Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!
Sailing in Honolulu · 12 guests

Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!

New
$999/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
Best of 2025
$180/hour
Waikiki Sunset Boat Charters and Custom Day Tours
Sailing in Honolulu · 6 guests

Waikiki Sunset Boat Charters and Custom Day Tours

5.0
$250/hour
Blue water Hawaiian Sailboat Cruise with USCG Licensed 100 Ton Captain
Sailing in Honolulu · 4 guests

Blue water Hawaiian Sailboat Cruise with USCG Licensed 100 Ton Captain

New
$150/hour
27ft Classic Sailboat
Sailing in Honolulu · 6 guests

27ft Classic Sailboat

New
$199/hour
Enjoy Oahu’s south shore and Waikiki on Rubicon, a beautiful 45’ private yacht
Powerboats 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

New
$550/hour
$99 per person/hr, 5 people minimum booking 3 hr minimum sailing required
Sailing in Honolulu · 12 guests

$99 per person/hr, 5 people minimum booking 3 hr minimum sailing required

New
$495/hour
***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***
Sailing in Honolulu · 12 guests

***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***

5.0
$99/hour
CHB 45ft Trawler for Charter in Honolulu
Powerboats in Honolulu · 6 guests

CHB 45ft Trawler for Charter in Honolulu

5.0
$350/hour
The SV Praha Luxury Sailing Yacht in Honolulu, Hawaii
Sailing in Honolulu · 6 guests

The SV Praha Luxury Sailing Yacht in Honolulu, Hawaii

5.0
$388/hour
Isara 50ft Sailing Catamaran, Ultimate Luxury and Quality
Sailing in Honolulu · 12 guests

Isara 50ft Sailing Catamaran, Ultimate Luxury and Quality

New
$1,200/hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 6 guests

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

5.0
Superowner
Best of 2025
$350/hour

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Kailua Reviews

  1. JG

    John

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

    Fantastic family outing. We brought poke and drinks on board for a 3 hour sunset cruise and snorkel. Our kids saw turtles and we had a great relaxing time. Enjoyed the trip and the company. Tony and Quinn were welcoming and shared their experiences from life. Thanks for providing exactly what I was looking for.

  2. GV

    Gemma

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

    I booked a private ride to do a photoshoot and Tony was super helpful with suggestions and what we needed. Everything went really seamless and I’m so grateful! Would definitely book again!

  3. LR

    Laura

    CHB 45ft Trawler for Charter in Honolulu

    The crew was great. We just relaxed and enjoyed our time on the water! Thank you so much for allowing us some good family time!

  4. Maroun

    Maroun

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

    Captain Tony went out of his way to help me with my proposal to my girlfriend. He called me a day before and he was happy to help with planning. We sailed out far enough where diamond head was in the backdrop of the proposal. While I was surprising my girlfriend he was taking photos and videos! Overall it was a great experience and highly recommend. We will certainly be touring with him again. Thank you!

  5. SC

    Stephanie

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

    Rented Tony’s Sail boat for my sister’s 30th! We had such a great time. He was very attentive with my group and shared his life experiences with us. Pretty cool life he as! Ask him. Will rent again if we come back!

  6. PA

    Paul

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

    Savannah and Tom were fantastic and showed us an absolutely fabulous time on the water. Beautiful Kat, day and wonderful captain/crew. Would def book again, thank you!