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    Longboat Key, Florida Boat Rentals

    Page 1 of 1 • 24 listings

    Captained 25' Regency Tritoon with Fuel Included
    Powerboats in Longboat Key · 10 guests

    Captained 25' Regency Tritoon with Fuel Included

    5.0
    $89+/hour
    2017 Leopard 40 - Luxury Sailing Catamaran - Anna Maria Island
    Sailing in Bradenton Beach · 12 guests

    2017 Leopard 40 - Luxury Sailing Catamaran - Anna Maria Island

    5.0
    Superowner
    Best of 2025
    $300+/hour
    Super Comfy 22’ Pontoon in Bradenton/ fuel included
    Powerboats in Bradenton Beach · 8 guests

    Super Comfy 22’ Pontoon in Bradenton/ fuel included

    4.9
    $57+/hour
    Sea Ray SDX 270 Yacht in Bradenton Beach, Florida
    Powerboats in Bradenton Beach · 10 guests

    Sea Ray SDX 270 Yacht in Bradenton Beach, Florida

    New
    $240/hour
    Cruise in style with this beautiful Center Console boat
    Powerboats in Cortez · 12 guests

    Cruise in style with this beautiful Center Console boat

    New
    $190/hour
    Fun and Adventure Await on a Brand-New Switch Sport!
    Powerboats in Bradenton Beach · 6 guests

    Fun and Adventure Await on a Brand-New Switch Sport!

    3.7
    $150/hour
    ⭐ FREE HOUR ⭐ LUXURY 3-Story Yacht including JET SKI ready for your adventure
    Events in Bradenton Beach · 13 guests

    ⭐ FREE HOUR ⭐ LUXURY 3-Story Yacht including JET SKI ready for your adventure

    5.0
    $580+/hour
    Instant Book
    The Outrageous 42' Boston Whaler on Anna Maria
    Powerboats in Bradenton Beach · 12 guests

    The Outrageous 42' Boston Whaler on Anna Maria

    5.0
    $379+/hour
    The Fabulous 50' “Lil’ Bit Nauti”
    Events in Bradenton Beach · 12 guests

    The Fabulous 50' “Lil’ Bit Nauti”

    5.0
    $550+/hour
    42ft Boston Whaler Outrage Prestige Luxury Boating
    Powerboats in Bradenton Beach · 13 guests

    42ft Boston Whaler Outrage Prestige Luxury Boating

    New
    $299+/hour
    Embark on a fishing trip with SeaHunt 22ft CC as you reel in the big one!!
    Fishing in Bradenton · 4 guests

    Embark on a fishing trip with SeaHunt 22ft CC as you reel in the big one!!

    New
    $125+/hour
    Sun Chaser DLX Pontoon for Long Term Rental delivered to your dock!
    Powerboats in Bradenton · 10 guests

    Sun Chaser DLX Pontoon for Long Term Rental delivered to your dock!

    New
    $320+/day
    51' TOP FUN, Luxury BIG Yacht. Sunset-dolphin cruise, Parties and more!
    Events in Tampa · 13 guests

    51' TOP FUN, Luxury BIG Yacht. Sunset-dolphin cruise, Parties and more!

    5.0
    $140+/hour
    Instant Book
    Sarasota Luxury Cruise on 38ft Silverton Yacht with Captain
    Events in Longboat Key · 6 guests

    Sarasota Luxury Cruise on 38ft Silverton Yacht with Captain

    New
    $339/hour
    Sylvan Tritoon with Yamaha 150 – Sandbars-Snorkeling-Cruising
    Powerboats in Holmes Beach · 12 guests

    Sylvan Tritoon with Yamaha 150 – Sandbars-Snorkeling-Cruising

    New
    $75/hour
    Spacious 12-Passenger Pontoon-Perfect for Vacations & Sandbar Hopping!
    Powerboats in Holmes Beach · 12 guests

    Spacious 12-Passenger Pontoon-Perfect for Vacations & Sandbar Hopping!

    New
    $75/hour
    Hurricane SunDeck Fun – Perfect for Sandbars, Sunset & Island Days!
    Powerboats in Holmes Beach · 12 guests

    Hurricane SunDeck Fun – Perfect for Sandbars, Sunset & Island Days!

    New
    $75/hour
    Sandbar and Island Hopping
    Tours in Holmes Beach · 12 guests

    Sandbar and Island Hopping

    5.0
    Superowner
    $200/hour
    Bayliner Trophy T22 Center Console Rental in Holmes Beach, Florida
    Powerboats in Holmes Beach · 10 guests

    Bayliner Trophy T22 Center Console Rental in Holmes Beach, Florida

    5.0
    $92+/hour
    2021 Cypress Cay tritoon, seats up to 13ppl
    Powerboats in Holmes Beach · 13 guests

    2021 Cypress Cay tritoon, seats up to 13ppl

    5.0
    $450/day
    Beautiful Bayliner DX2200 | Perfect for a day exploring AMI!
    Powerboats in Holmes Beach · 12 guests

    Beautiful Bayliner DX2200 | Perfect for a day exploring AMI!

    5.0
    $429+/day
    Big Grey, our Gorgeous 23' Bayliner Deck Boat with sports tower!
    Powerboats in Holmes Beach · 12 guests

    Big Grey, our Gorgeous 23' Bayliner Deck Boat with sports tower!

    5.0
    $82+/hour
    25’ “Easy Livin” Double Decker Pontoon (Captain Included)
    Powerboats in Holmes Beach · 6 guests

    25’ “Easy Livin” Double Decker Pontoon (Captain Included)

    New
    $140+/hour
    2021 New Cypress Cay 23ft Tritoon Boat for Rent in Holmes Beach!!
    Powerboats in Holmes Beach · 13 guests

    2021 New Cypress Cay 23ft Tritoon Boat for Rent in Holmes Beach!!

    5.0
    $425+/day

    Top Destinations Nearby

    Longboat Key Reviews

    1. TG

      Troy

      Super Comfy 22’ Pontoon in Bradenton/ fuel included

      Tom was our host. He gave us great instruction for operating the boat and navigating the intercoastal water ways.

    2. LS

      Logan

      2017 Leopard 40 - Luxury Sailing Catamaran - Anna Maria Island

      Excellent service, fantastic boat, beautiful sunset.

    3. TE

      Thomas

      ⭐ FREE HOUR ⭐ LUXURY 3-Story Yacht including JET SKI ready for your adventure

      Fantastic experience. Great boat with Seadoo!

    4. JK

      Jessica

      Captained 25' Regency Tritoon with Fuel Included

      We had a wonderful day with Shawn. Prior to trip he was very communicative and easy to plan with. I can confidently say it was the best day for the family! The boat is pristine, he was so friendly and his love of the ocean made for an unforgettable day.

    5. LM

      Lesley

      Captained 25' Regency Tritoon with Fuel Included

      Truly awesome day on the water with Shawn. Great communication. Easy directions for where to meet him. Impeccable boat that was so comfortable. Cooler with ice. Comfy floats. And great recommendations for our itinerary. Definitely booking with him again next year!

    6. JB

      Jennifer

      Captained 25' Regency Tritoon with Fuel Included

      Everything from the boat to the itinerary to Captain Shawn himself were more perfect than you could possibly imagine! He had the perfect day planned based on what we said we were looking for and he hit every mark. He made sure the kids had a day to remember and the adults got to relax! He even made sure we always had a drink in hand from the cooler we stuffed full of drinks and snacks. I cannot say enough wonderful things about Captain Shawn. He’s part of the family now and we’ll never book with anyone else. Thank you for the perfect day on the water! ❤️

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