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Captain

Browse Boat Rentals on Anna Maria Island, Florida.

Page 1 of 118 listings

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-$120hour
Bentley Pontoon Rental in Holmes Beach, Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon Rental in Holmes Beach, Florida

5.0
$62-$87hour
Bentley Encore Pontoon Holmes Beach, Anna Maria Island, Bradenton
Powerboats in Holmes Beach · 13 guests

Bentley Encore Pontoon Holmes Beach, Anna Maria Island, Bradenton

4.9
$70hour
Charter this brand new 2023 25ft Yamaha AR250 Jetboat in Holmes Beach
Powerboats in Holmes Beach · 8 guests

Charter this brand new 2023 25ft Yamaha AR250 Jetboat in Holmes Beach

5.0
$120hour
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Powerboats in Holmes Beach · 8 guests

New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!

4.9
$372-$515day
Island Hopper Anna Maria Tiki - Up to 18ppl
Powerboats in Holmes Beach · 18 guests

Island Hopper Anna Maria Tiki - Up to 18ppl

New
$250hour
''Princess Abu II'' Prestige Flybridge 630 Yacht Charter in Anna Maria, Florida
Events in Anna Maria · 12 guests

''Princess Abu II'' Prestige Flybridge 630 Yacht Charter in Anna Maria, Florida

5.0
$1,077hour
"VayCay" 52' Prestige in Anna Maria Island, FL
Events in Anna Maria · 12 guests

"VayCay" 52' Prestige in Anna Maria Island, FL

5.0
$805hour
"ALLEGRIA' is a 24,2" Hurricane with bimini and plenty of seating.
Powerboats in Holmes Beach · 6 guests

"ALLEGRIA' is a 24,2" Hurricane with bimini and plenty of seating.

5.0
Superowner
$135hour
2 Hour, 3 Hour and 4 Hour Boat with Captain - Anna Maria Island
Powerboats in Bradenton Beach · 6 guests

2 Hour, 3 Hour and 4 Hour Boat with Captain - Anna Maria Island

5.0
$120hour
2018 Stott Craft Bay 22ft Boat with Captain
Powerboats in Holmes Beach · 6 guests

2018 Stott Craft Bay 22ft Boat with Captain

5.0
$70hour
Cruise in style with this beautiful Center Console boat
Powerboats in Cortez · 12 guests

Cruise in style with this beautiful Center Console boat

New
$190hour
"Dryft" Viking 44 Open Yacht for Charter in Anna Maria, Florida
Fishing in Anna Maria · 12 guests

"Dryft" Viking 44 Open Yacht for Charter in Anna Maria, Florida

New
$833hour
"Nauti Girl" Carver 570 Voyager
Events in Bradenton · 12 guests

"Nauti Girl" Carver 570 Voyager

New
$808hour
"Prestige Worldwide" 68' Prestige 680
Events in Anna Maria · 12 guests

"Prestige Worldwide" 68' Prestige 680

New
$1,207hour
Nearshore Fishing Trip with Captain Alex in Bradenton
Fishing in Bradenton · 4 guests

Nearshore Fishing Trip with Captain Alex in Bradenton

New
$142-$163hour
Fun N Sun in Paradise - Cypress Cay Seabreeze Spacious Pontoon
Powerboats in Holmes Beach · 10 guests

Fun N Sun in Paradise - Cypress Cay Seabreeze Spacious Pontoon

New
$75hour
Inshore Fishing Trip for 4 anglers in Bradenton with Captain Alex
Fishing in Bradenton · 2 guests

Inshore Fishing Trip for 4 anglers in Bradenton with Captain Alex

New
$100-$125hour

Anna Maria Island Reviews

  1. PN

    Pete

    Bentley Pontoon Rental in Holmes Beach, Florida

    This was a great match for our mature group of nine. Captain Dana took us to interesting places while sharing her local knowledge. We saw dolphins and a manatee or two while also getting our feet wet on a sandbar. Great value and experience for us

  2. AK

    Ansley

    Charter this brand new 2023 25ft Yamaha AR250 Jetboat in Holmes Beach

    We had an absolute blast. Captain John took us all around. We started with a stop at a sandbar for some swimming and drinks. Both daughters used the snorkel masks. We then took a long cruise. We ended our journey by spotting a pod of dolphins leading us home. I would strong recommend this for anyone looking for a fun family adventure.

  3. RH

    Ron

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

    From the beginning of our experience with Wynot Rent A Boat, they were very flexible to our preferences for boat pickup. The pontoon boat was delivered to us at a very convenient location. Everything worked very well, resulting in a beautiful memorable day. We will definitely use them again. Ron H…

  4. Edlexander

    Edlexander

    Bentley Pontoon Rental in Holmes Beach, Florida

    Forgot to write a review from original use but coming back to request another date for usage because of how easy and painless the process was and how helpful KarrieMike were ! The boat was in great condition and was perfect for the guys trip

  5. Tracy

    Tracy

    Bentley Pontoon Rental in Holmes Beach, Florida

    I had an incredible experience renting a boat from Karrie and Mike! From start to finish, they provided exceptional service. The boat itself was comfortable and spacious, easily accommodating our party of 7. Karrie and Mike were fantastic in their communication. They were super quick to respond during the booking phase. They had great patience when we encountered unexpected traffic and arrived late too. They made sure we felt at ease throughout the process, even willing to guide us live via phone when we had technical questions about the boat. Captain Larry, who accompanied us on our trip, was an absolute gem. He took us to all the best spots, ensuring we had a memorable time. The highlight was when we spotted dolphins—it was truly magical! Captain Larry's expertise and friendly demeanor enhanced our overall experience. I couldn't have asked for a better boat rental experience. Karrie, Mike, and Captain Larry surpassed our expectations in every way. Their attention to detail, excellent communication, and dedication to ensuring our enjoyment made this trip unforgettable. I highly recommend their services to anyone looking for an outstanding boating adventure.

  6. SB

    Stephanie

    Bentley Pontoon Rental in Holmes Beach, Florida

    Great experience overall! We were happy to find a boat that fit all 13 of us at a good price. Communication and boat instructions from Mike were top notch! We rented the float mat as well and all the kids LOVED it! We stopped at Passage Key and Egmont Key. Highly recommend Mike!