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Anchor Down and Explore: Our Guide to the Top Boat Rentals and Charters on Anna Maria Island

a boat is docked next to a body of water

The Perfect Place for Boat Rentals

With over 11,000 miles of rivers, streams, and waterways, Florida is a boater’s paradise. Anna Maria Island, located on Florida’s Gulf Coast, is an especially popular destination for recreational boaters. The island’s warm clear waters, sandy beaches, and laid-back charm make it the ideal place for a day on the water. Whether you want to go fishing, dolphin watching, or simply cruise along the Intracoastal Waterway, renting a boat is one of the best ways to experience Anna Maria Island and its surrounding areas.

Book your rental now. Call Pirate Monkey Boat Rentals at 941-735-8385 or book online at Pirate Monkey Boat Rentals

Overview of Boat Rentals in the Anna Maria Island Area

The Anna Maria Island area of Florida is a boater’s paradise with its beautiful beaches, calm waters, and abundance of marine wildlife. There are many options for boat rentals in the towns surrounding Anna Maria Island.

Bradenton, located on the mainland just east of Anna Maria, is home to numerous marinas and boat rental companies. You can rent pontoon boats, power boats, fishing boats, and other watercraft to explore the Intracoastal Waterway and nearby bays and islands. Popular launch points in Bradenton include Bradenton Beach Marina, Regatta Pointe Marina, and Twin Dolphin Marina.

The city of Sarasota, about 30 minutes south of Anna Maria, also has plenty of boat rental outlets. You’ll find options to launch from Marina Jack, O’Leary’s Tiki Bar & Grill, CB’s Saltwater Outfitters, and Sarasota Sailing Squadron. Rentals include power boats, sailboats, personal watercraft like jet skis, and fishing charters.

On Longboat Key, the strip of land just south of Anna Maria, boat rentals are available through Cannons Marina and Freedom Boat Club Longboat Key. You can charter boats of all sizes and explore the gorgeous turquoise waters of the Gulf of Mexico.

No matter where you launch from, you’ll have easy access to dipping your toes in the sand on Anna Maria’s pristine beaches from the deck of your rented boat.

Types of Boats Available for Rent

Anna Maria Island offers a variety of boats to meet your needs for a day on the water. Here are some of the most popular rentals:

Pontoon Boats

Pontoon boats are ideal for cruising the calm waters around Anna Maria with a group. With space for 8-12 people, an enclosed deck, and plenty of room to relax, they’re perfect for parties or taking the whole family out. Many pontoon rentals come equipped with amenities like Bluetooth speakers, plenty of dry storage and canopy tops for shade.

Fishing Boats

For anglers looking to cast a line, center console fishing boats offer stability and open layouts. Leaning posts with rod holders keep your gear secure while standing up to fish. Livewells and bait prep stations allow you to keep your bait lively. Shallow draft hulls can navigate flats and backwaters in search of snook, redfish, and trout.

Jet Skis

Zip around on your own personal watercraft, like Yamaha or Sea-Doo jet skis built for speed and agility. Many places offer solo skis, but tandem models allow you to take a passenger along for the ride. Jet skis are a thrilling way to explore Anna Maria’s coastline and sandbars.

Power Catamarans

These twin-hulled powerboats provide a smooth, stable ride for smaller groups. With capacity for 6-8 people, they’re ideal for island hopping, snorkeling excursions, or just relaxing on the water. Many feature canvass Bimini tops, rear swim platforms, and boarding ladders.


Paddle your way around the shallow mangrove shores and seagrass flats of Anna Maria. Single and tandem kayaks allow you to explore hard-to-reach areas and get an upper body workout at the same time. Many kayak rentals include gear like paddles, life jackets, dry storage bags, and seat cushions. Guided kayak eco-tours are also available.

With so many options, you’re sure to find a rental boat perfect for your Anna Maria Island getaway.

Top Boat Rental Companies

Anna Maria Island offers several excellent boat rental companies to choose from. Here are some of the top options for renting a boat and getting out on the water:

Pirate Monkey Boat Rentals

Pirate Monkey Boat Rentals is the premier choice for pontoon boat rentals and boat charters near Anna Maria Island. They have a large fleet of pontoon boats that can accommodate groups of up to 12 people. Pirate Monkey offers full and half-day rental options, with 4, 6, or 8 hour rentlas. Their experienced captains provide a personalized orientation to ensure renters feel comfortable operating the boats. Pirate Monkey Boat Rentals has an excellent reputation for providing fun, reliable boat rentals in the area.

Ariel Boat Rentals

Ariel Boat Rentals provides power boats and pontoon boats for rent by the hour or full day. They have a convenient online booking system to reserve boats. Ariel Boat Rentals includes fuel costs in their rental pricing and provides complimentary life jackets. Their fleet ranges from small skiffs to large party pontoons that can hold 12 passengers. This company offers reliable boat rentals at competitive rates.

AMI Boat Rentals

For a more personalized boat rental experience, AMI Boat Rentals is a great local option. They have a smaller fleet of well-maintained boats available for full or half-day rental. In addition to power boats and pontoons, AMI Boat Rentals offers kayaks and stand-up paddleboards. Their staff provides hands-on orientation and can suggest custom itineraries to explore Anna Maria Island by boat. AMI Boat Rentals focuses on providing exceptional customer service.

Benefits of Renting with Pirate Monkey

Pirate Monkey Boat Rentals stands out as the top choice for pontoon boat rentals and charters near Anna Maria Island for several key reasons:

  • Modern, High-Quality Boats: Pirate Monkey’s fleet consists of late-model, well-maintained pontoon boats that can accommodate parties of up to 12 passengers. Their boats feature comfortable seating, Bimini tops for shade, Bluetooth stereos, and plenty of storage space.
  • Experienced, Friendly Staff: The staff at Pirate Monkey are extremely knowledgeable about operating the boats safely and navigating local waters. They provide an in-depth orientation and answer any questions you have before departure. Their top priority is ensuring renters have a fun, safe experience.
  • Flexible Booking: Pirate Monkey makes it easy to book online and offers half-day, full-day, and custom multi-day rentals. You can choose from morning, afternoon or full-day options. Reservations can be made last-minute in many cases.
  • Ideal Location: Pirate Monkey’s marina is conveniently located on the north end of Anna Maria Island, providing quick access to Tampa Bay, Palma Sola Bay, the Intracoastal Waterway, and Gulf beaches. This allows renters to reach the best boating and beaching spots easily.

With its modern fleet, great service, and prime location, Pirate Monkey Boat Rentals is the top choice for enjoying Anna Maria Island’s beautiful waters by pontoon boat.

Boating Activities Near Anna Maria

The waters around Anna Maria Island provide endless opportunities for fun on the water. Here are some of the most popular boating activities in the area:

Snorkeling and Scuba Diving

The clear waters and coral reefs make for excellent snorkeling and scuba diving. Some top spots include Bean Point, the Anna Maria City Pier, and Robinson Preserve. The diverse marine life includes sea turtles, rays, sharks and tropical fish. Many rental companies offer snorkel gear and can advise the best spots.


Fishing is hugely popular in the area. Options include inshore fishing for snook, redfish and trout. There’s also great offshore fishing for grouper, snapper, shark and tarpon. The nearby Skyway Fishing Pier is another hot spot. Rentals often provide rods, bait and tackle.

Island Hopping

One fun activity is to cruise between the islands like Anna Maria, Longboat Key and Lido Key. Rentals allow you to access secluded beaches and hidden coves. Pack a picnic lunch and make a day of exploration.

Sunset Cruises

A sunset cruise is a classic experience, with boats departing in the late afternoon. There are few better places to watch the sunset than from a boat with a cold drink in hand. Dolphin sightings are common too.

Private Charters

Many companies offer private charters, allowing you to customize the itinerary. Options include everything from family trips to champagne cruises. Charters work for special occasions like birthdays, anniversaries and proposals.

Safety Tips for Renters

When renting a boat in the Anna Maria Island area, safety should be your top priority. Here are some important tips to keep in mind:

  • Always check the weather forecast before heading out. Storms can pop up quickly in Florida, so be prepared to postpone your trip if thunderstorms are likely.
  • Require all passengers to wear life jackets at all times. This is especially important for children. Make sure the life jackets are properly fitted.
  • Follow all boating regulations set forth by the Florida Fish and Wildlife Conservation Commission and the U.S. Coast Guard. This includes speed limits, no wake zones, and other rules.
  • Never operate the boat while under the influence of alcohol or drugs. A sober captain is an absolute must.
  • Let others know your float plan, including where you are going and when you expect to return. Give them a way to reach you in case of emergency.
  • Bring essential safety gear like flares, fire extinguisher, first aid kit, anchor, and flashlight even for short day trips.
  • Keep an eye out for swimmers, manatees, dolphins and other boats. Practice safe navigation at all times.
  • Don’t overload the boat. Follow the maximum capacity limits. Too much weight can affect handling and stability.
  • Ask for a thorough instruction on how to operate the boat before heading out, especially if you are renting a new style or size of vessel.

Following basic boating safety tips will help ensure your rental experience is smooth sailing. Stay alert and be prepared so you can have fun on the water!

Cost of Boat Rentals

The cost of renting a boat can vary greatly depending on the type of vessel and length of rental. Here are some average prices for rentals around Anna Maria Island:

  • Pontoon boats – $150-$300 for 4 hours. 24 foot pontoons for 6 people are around $200 for 4 hours. Larger 30 foot pontoons for 10 people range from $250-$400+ for 4 hours.
  • Power boats – Smaller center console boats like a 18-22 foot Bayliner can run $200-$300 for 4 hours. Larger offshore fishing boats like a 25 foot Contender are $400-$600 for 4 hours.
  • Sailboats – Small one or two person sailboats like a Sunfish are $50-$75 per hour. Mid-size vessels like a 25 foot Catalina are around $150-$200 per hour. Larger 40+ foot sailboats can be $300+ per hour.
  • Jet skis – Single rider jet skis are approximately $100 per hour. Two person jet skis are $150-$200 per hour.
  • Kayaks – Single kayak rentals are around $25-$35 per hour or $50-$60 for 4 hours. Two person kayaks are $35-$50 per hour.

Rentals for half or full days are also available, which helps lower the hourly rate. Overall boat rental prices can fluctuate based on demand, so it helps to book in advance for the best rates.

How to Book a Boat Rental

Booking a boat rental in Anna Maria Island is easy whether you plan to visit for a day or a full vacation. Here are some tips for reserving your perfect boat rental:

  • Book Early – The peak season for boat rentals is between March and August. Reserve your rental at least 2-3 months in advance to ensure availability and the best rates. Last minute bookings will be limited.
  • Determine Group Size – Consider how many people will be on the boat. Rental companies offer everything from small skiffs to 12-passenger pontoons. Make sure to choose a boat that fits your group comfortably.
  • Select Departure Time and Duration – Most companies offer full or half day rentals. Pick a start time and duration that allows you to experience everything you want. For beaching and island hopping, at least 4 hours is recommended.
  • List Desired Amenities – Upgrade options may include features like convenience kits, premium stereos, canopy tops and more. Know what features will enhance your time on the water.
  • Arrange Travel To/From Marina – Boat departures are from marinas, so factor in travel time to arrive for your check-in. Many companies offer complimentary transportation to/from area hotels.
  • Read Reviews and Compare – Research the best rental companies for service, quality and value. This ensures you choose a provider that meets your needs.
  • Book Online or Call – Most boats can be reserved on company websites. For questions, call to speak with a rental agent who can assist you.

Booking your Anna Maria boat rental in advance with the right company will start your vacation off smoothly and on the water.


Anna Maria Island is a boater’s paradise, with its beautiful beaches, calm waterways, and accessibility to the Gulf of Mexico. This guide has covered the top boat rental companies in the area, the types of boats available, and the many wonderful destinations reachable by boat from AMI.

While there are several great rental providers to choose from, Pirate Monkey Boat Rentals stands out as the premier option for pontoon boats and custom excursions. Their modern fleet, experienced captains, and focus on customer service make them the top choice for creating unforgettable memories on the water.

So don’t delay – book your Anna Maria Island boat rental today! With the right boat and a sense of adventure, you’ll be enjoying this island paradise to the fullest. Charter a fishing trip, gather friends on a pontoon, or customize a private cruise. The options are endless when you get out on the water. Reserve your rental boat now and start planning the Anna Maria Island boating vacation you’ve been dreaming of.

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