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All listings in Anna Maria Island

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

Page 1 of 122 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
2025 SPECIAL - Add-Ons Included! Pontoon Seats 12!
Powerboats in Holmes Beach · 12 guests

2025 SPECIAL - Add-Ons Included! Pontoon Seats 12!

5.0
$56+/hour
24' Tritoon Bennington with 175 Hp Suzuki Outboard for rent in Holmes Beach!
Powerboats in Holmes Beach · 12 guests

24' Tritoon Bennington with 175 Hp Suzuki Outboard for rent in Holmes Beach!

4.8
$85/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
Luxury Pontoon with Free Add-Ons: Seats 12! – Sun Tracker Party Barge
Powerboats in Holmes Beach · 12 guests

Luxury Pontoon with Free Add-Ons: Seats 12! – Sun Tracker Party Barge

5.0
$56+/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
24' Tritoon Bennington with 175 Hp Suzuki motor for rent in Bradenton
Powerboats in Bradenton · 12 guests

24' Tritoon Bennington with 175 Hp Suzuki motor for rent in Bradenton

4.8
$85/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
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
Sandbar and Island Hopping
Tours in Holmes Beach · 12 guests

Sandbar and Island Hopping

5.0
Superowner
$200/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
Bar Crawl Booze Cruise
Powerboats in Holmes Beach · 6 guests

Bar Crawl Booze Cruise

5.0
Superowner
$166/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
24ft Sun Tracker Fish Barge DLX Pontoon in Bradenton Beach
Powerboats in Holmes Beach · 10 guests

24ft Sun Tracker Fish Barge DLX Pontoon in Bradenton Beach

5.0
$65+/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
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

5.0
$127+/hour
Instant Book
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
Bennington Tritoon 150HP fishing series Sx21
Powerboats in Holmes Beach · 12 guests

Bennington Tritoon 150HP fishing series Sx21

New
$60+/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
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
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

Pontoon Reviews in Anna Maria Island

  1. MA

    Marco

    2025 SPECIAL - Add-Ons Included! Pontoon Seats 12!

    I had an incredible experience renting a boat from Jeff! From start to finish, he made the process easy, stress-free, and fun. The boat was in excellent condition—clean, well-maintained, and ready to go when I arrived. Jeff was friendly, knowledgeable, and gave clear instructions so I felt confident on the water. He truly went above and beyond to make sure I had a great time. I can’t recommend him enough—if you’re thinking about renting a boat, Jeff is the person to go to!

  2. NA

    Nicholas

    24' Tritoon Bennington with 175 Hp Suzuki Outboard for rent in Holmes Beach!

    An excellent pontoon for our group! A nice pontoon with all the space we needed. We explored Egmont Key and did some fishing. Highly recommend renting from Karrie and Mike and spending the day on the water.

  3. CA

    Catherine

    24ft Sun Tracker Fish Barge DLX Pontoon in Bradenton Beach

    Everything went very smooth. No complaints. If you need a pontoon to relax on the water this is it. It’s a double bimini, the entire boat can be shaded. They had 4 adult life vest and plenty of kid vest, double anchor ⚓️ is a plus, Bluetooth speaker, ice machine is at the dock location, we had our own cooler however we could have simply brought our snacks. Cooler and Extra storage is on pontoon. If you have a group this is the right choice. 10/10

  4. AL

    Aaron

    Luxury Pontoon with Free Add-Ons: Seats 12! – Sun Tracker Party Barge

    Where to start? Jeff did an amazing job right from the start when I first messaged him with questions pertaining to his pontoon rental. Polite, courteous, and offered everything we could even want in a rental. He provided chairs, snorkel equipment, a floating mat, paid for the gas, and even asked if he could get anything else for us that wasn’t listed. Jeff even upgraded us to his newest boat and kept the same price we were quoted for his second less expensive boat when that boat booked up. Jeff showed up when we were kinda in a pickle out on the water and got us back straight. He kept us up to date with all the weather updates throughout the day so we didn’t have to do it ourselves. Hands down this was the best rental I’ve ever booked, and the hospitality and professionalism Jeff showed was out of this world!

  5. LL

    Lonnie

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

    My family rented a house with a dock on Annamarie Island, Florida We rented a tritoon boat from Meghan R which was absolutely seamless! We were able to dock the boat at our rental house and explore and fish at our own leisure What a pleasure it was renting from Meghan R My family thank you for making our vacation extra special

  6. AB

    Ashley

    2025 SPECIAL - Add-Ons Included! Pontoon Seats 12!

    My party of 11 and I had the most wonderful time on the boat for my birthday. Jeff was quick to respond, thoughtful, and made the first time boat rental experience seamless and stress-free. I wouldn’t hesitant to rent from him again!