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Holmes Beach, Florida Boat Rentals

Page 1 of 116 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+/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 Pontoon on Anna Maria Island,  Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon on Anna Maria Island, Florida

5.0
$70/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
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
ALLEGRIA is a 24ft Hurricane with bimini and plenty of seating.
Powerboats in Holmes Beach · 6 guests

ALLEGRIA is a 24ft Hurricane with bimini and plenty of seating.

5.0
Superowner
$130/hour
Charter this 2023 25ft Yamaha AR250 Jetboat in Anna Maria Island
Powerboats in Holmes Beach · 8 guests

Charter this 2023 25ft Yamaha AR250 Jetboat in Anna Maria Island

5.0
$120/hour
Instant Book
''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
$1,077/hour
Luxury Power Boat..Can Fit Large Groups...Dolphin Tour!!!!!
Events in Anna Maria · 12 guests

Luxury Power Boat..Can Fit Large Groups...Dolphin Tour!!!!!

5.0
$300/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
The Outrageous 42' Boston Whaler on Anna Maria
Powerboats in Holmes Beach · 12 guests

The Outrageous 42' Boston Whaler on Anna Maria

New
$324+/hour
"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
$833/hour
"Charlotte" Prestige X70
Events in Anna Maria · 12 guests

"Charlotte" Prestige X70

New
$1,548/hour

Holmes Beach Reviews

  1. 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…

  2. BJ

    Brian

    Bentley Pontoon Rental in Holmes Beach, Florida

    The whole rental experience was pleasant. Rich was on time with the boat at the dock he was direct with his instructions even though I have plenty of experience navigating FL waterways. The boat was clean ran well and was equipped with everything we needed! Thanks again would highly recommend.

  3. 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

  4. 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.

  5. 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!

  6. SB

    Sommer

    Bentley Pontoon Rental in Holmes Beach, Florida

    We booked this boat because it was a good price, could handle our group of 11, and available. We boat all over the place (my parents have houses on Norris Lake and Bonita Beach), but this was our first time in the Sarasota Bay. The boat was in great shape, all safety items on board, and exactly as described. We were given a good run down on the basics of the boat and off we went. Beautiful boating to be had all over!! The parking was free and ramp easy to find. We will most definitely use them again! Thank you!