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Anna Maria Island, US Boat Rentals & Yacht Charters

4.9

(726 Reviews)

Page 2 of 2 • 44 listings

Powerboats in Holmes Beach · 12 guests

Hurricane SunDeck Fun – Perfect for Sandbars, Sunset & Island Days!

5.0

$75+/hour

Powerboats in Bradenton Beach · 10 guests

Sea Ray SDX 270 Yacht in Bradenton Beach, Florida

5.0

$240/hour

Powerboats in Holmes Beach · 10 guests

Sun Tracker 22’ Party Barge Pontoon in Holmes Beach

5.0

$100/hour

Events in Anna Maria · 12 guests

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

5.0

$921/hour

Powerboats in Holmes Beach · 8 guests

Chill at the Sandbar on Pioneer 202 Sportfish Boat

New

$90/hour

Events in Tampa · 13 guests

Best Deal | 51’ Luxury Performance Formula Yacht in Bradenton Beach

New

$300+/hour

Powerboats in Bradenton Beach · 13 guests

42ft Boston Whaler Outrage Prestige Luxury Boating

New

$299+/hour

Powerboats in Holmes Beach · 13 guests

"The Escape Plan" 33' Boston Whaler Center Console in Anna Maria Island, Florida

New

$310/hour

Fishing in Anna Maria · 12 guests

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

New

$833/hour

Powerboats in Cortez · 12 guests

Cruise in style with this beautiful Center Console boat

New

$190/hour

Events in Anna Maria · 12 guests

"Charlotte" Prestige X70

New

$1,548/hour

Powerboats in Terra Ceia · 12 guests

Brand New Bentley Tritoon 150hp | Up to 13 | Cruise, Fish, and Water Sports

New

$81+/hour

Powerboats in Holmes Beach · 6 guests

25’ “Easy Livin” Double Decker Pontoon (Captain Included)

New

$140+/hour

Events in Anna Maria · 13 guests

Princess 75' Mega Yacht for Charter

New

$1,828/hour

Events in Anna Maria · 12 guests

Prestige 59' Motor Yacht | Anna Maria, Florida

New

$1,050/hour

Powerboats in Bradenton · 10 guests

Sun Chaser DLX Pontoon for Long Term Rental delivered to your dock!

New

$320+/day

Events in Bradenton Beach · 6 guests

Anna Maria Island Yacht Tour | Axopar 37 XC Cross Cabin Boat with AC!

New

$275+/hour

Fishing in Bradenton · 4 guests

Nearshore Fishing Trip with Captain Alex in Bradenton

New

$142+/hour

Fishing in Bradenton · 2 guests

Inshore Fishing Trip for 4 anglers in Bradenton with Captain Alex

New

$100+/hour

Powerboats in Bradenton · 10 guests

22' Family Friendly Pontoon in Palmetto, Florida

5.0

Snoozed - Active 24 Oct 2026

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Anna Maria Island Reviews

Richard

22' Family Friendly Pontoon in Palmetto, Florida
We couldn’t have wished for a nicer person to deal with. Nothing was too much and the advice and recommendations were so helpful. Thank you so very much!
CK
Cheryl

22' Family Friendly Pontoon in Palmetto, Florida
Winston was wonderful to communicate with, very responsive and easy to coordinate with. He was right on time for both departure and pickup, which made everything seamless. The whole experience was smooth, stress-free, and so much fun. We had a blast!
Ricki

22' Family Friendly Pontoon in Palmetto, Florida
Very helpful and understanding when we got stuck in low tide seaweed. He sent someone to our rescue and was very sympathetic. Other than that, we had a great day at Jewfish Key.
AP
Arun

22' Family Friendly Pontoon in Palmetto, Florida
Winston was an amazing and his boat was fun to drive and enjoy. Will rent from him again within a heartbeat.
km
kevin

22' Family Friendly Pontoon in Palmetto, Florida
Winston and his brother Jason could not have been more helpful and accommodating for our outing. We highly recommend them and would absolutely use them again!! Kevin M
BF
Bj

22' Family Friendly Pontoon in Palmetto, Florida
Renting with Winston always a pleasure. Everything was smooth from getting the boat and drop off back at the dock. Will be renting from Winston again in the future.