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All listings in Anna Maria Island

Search Pontoon Boat Rentals in Anna Maria Island, United States.

Page 1 of 111 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
BEAUTIFUL Bennington TRITOON 150 HP Holmes Beach , Anna Maria Fishing Series
Powerboats in Holmes Beach · 12 guests

BEAUTIFUL Bennington TRITOON 150 HP Holmes Beach , Anna Maria Fishing Series

5.0
$60+/hour
Bentley Pontoon Rental in Holmes Beach, Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon Rental in Holmes Beach, Florida

5.0
$62+/hour
Bentley Encore Pontoon Holmes Beach, Anna Maria Island, Bradenton
Powerboats in Holmes Beach · 13 guests

Bentley Encore Pontoon Holmes Beach, Anna Maria Island, Bradenton

5.0
$70/hour
Bentley Pontoon on Anna Maria Island,  Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon on Anna Maria Island, Florida

5.0
$70/hour
Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours
Tours in Holmes Beach · 6 guests

Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

5.0
Superowner
$175/hour
Bennington Tritoon -Fishing option-Holmes Beach on Anna Maria Island
Powerboats in Holmes Beach · 12 guests

Bennington Tritoon -Fishing option-Holmes Beach on Anna Maria Island

4.0
$65+/hour
LUXURIOUS AND SPACIOUS PARTY BOAT - BRAND NEW TRITOON
Powerboats in Anna Maria · 12 guests

LUXURIOUS AND SPACIOUS PARTY BOAT - BRAND NEW TRITOON

5.0
Best of 2025
$110/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
Luxury Bennington Tritoon 150HP fishing series Sx21
Powerboats in Holmes Beach · 12 guests

Luxury Bennington Tritoon 150HP fishing series Sx21

New
$60+/hour
Captained, Anna Maria sandbars from Jewfish to clothing optional Passage Key
Powerboats in Holmes Beach · 6 guests

Captained, Anna Maria sandbars from Jewfish to clothing optional Passage Key

New
$125+/hour

Pontoon Reviews in Anna Maria Island

  1. 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.

  2. Elizabeth

    Elizabeth

    Captained 25' Regency Tritoon with Fuel Included

    We had such a great day with Shawn! He was very kind and attentive, and so patient with our large group! Love that he brought us little bags for our kids’ seashells. Will definitely have him take us for the day when we return!

  3. Paul

    Paul

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

    Awesome captain and awesome boat cruise. Can’t wait to do it again!

  4. AR

    Alex

    Captained 25' Regency Tritoon with Fuel Included

    Shawn was amazing! Showed myself and friends from out of town a great time

  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! ❤️