Cookies!

We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.

All listings in Anna Maria Island

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

Page 1 of 118 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
BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.
Powerboats in Holmes Beach · 8 guests

BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.

5.0
$73+/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
24' Tritoon Bennington with new 175 Hp Suzuki Outboard for rent in Holmes Beach!
Powerboats in Holmes Beach · 12 guests

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

4.8
$85/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
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
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
Fun and Adventure Await on a Brand-New Switch Sport!
Powerboats in Bradenton Beach · 8 guests

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

3.0
$150/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
Instant Book
Bentley Pontoon on Anna Maria Island,  Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon on Anna Maria Island, Florida

5.0
$70/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
Luxury Bennington Tritoon 150HP fishing series Sx21
Powerboats in Holmes Beach · 12 guests

Luxury Bennington Tritoon 150HP fishing series Sx21

New
$60+/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
24' Tritoon Bennington with new 175 Hp Suzuki motor for rent in Bradenton
Powerboats in Bradenton · 12 guests

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

5.0
$85/hour
Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now
Powerboats in Holmes Beach · 10 guests

Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now

5.0
$375/day
Super Comfy 22’ Pontoon in Bradenton/ fuel included
Powerboats in Bradenton Beach · 10 guests

Super Comfy 22’ Pontoon in Bradenton/ fuel included

4.9
$57+/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
Instant Book
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. CS

    Cherie

    Bentley Encore Pontoon Holmes Beach, Anna Maria Island, Bradenton

    Great rental experience. Unfortunately the ladder was broken which made getting from the water (anchored in shallow water) back onto the boat difficult for some of our party. If renting this boat and you plan to use the ladder I would ask if this was fixed prior to departure. Boat was roomy and comfortable and communication was great. Thank you!

  2. DC

    DAWN

    Captained 25' Regency Tritoon with Fuel Included

    Capt. Shawn was exceptionally knowledgeable of the areas he took us to. His boat was immaculate and he was very accommodating. I would absolutely recommend Capt. Shawn!

  3. 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!

  4. 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! ❤️

  5. ST

    Shamyl

    BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.

    The best boat rental I’ve ever had! The customer service was out of this world, so amazing! Jeff was so helpful and gave us all the info and tools we needed to have a fun and safe time in the water. The boat was also incredible, road so smooth and easy to drive. If you’re going to book a boat, this is the best place to do it!

  6. Mike

    Mike

    BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.

    Jeff made everything easy. Everything from quick communication through text message to having the boat already in the water and ready to go when we showed up to the dock. Not to mention the top notch equipment he had for us. It was an amazing experience and I will definitely be using him again on our next trip to Anna Maria Island!!!