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  • Pontoon
    Within 100 Miles Of
    Winter Garden, Florida

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Pontoon boats for sale in Winter Garden Florida

There are 229 new and used Pontoon boats for sale in Winter Garden, Florida. Explore Pontoon brands like Sea Doo, Bennington, Sun Tracker, Godfrey, Sylvan, and Harris on BoatCrazy. View a wide selection of Pontoon boats from $4,977 to $250,000.
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  • Boats
  • Pontoon
    Within 100 Miles Of
    Winter Garden, Florida
229 boats found within 100 miles from Winter Garden, Florida
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  • 2026 Bennington 188SFCSF

    2026 Bennington 188SFCSF

    $42,793
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 19' / 0'
    • 2026 / New
    • $42,793

    If your ideal weekend involves a blend of relaxation and reeling in a big one, look no further. This Bennington S-Series, configured as the ultimate Fish and Cruise machine, is cra... View Details

    View 17 Photos and Details Contact Seller
    $42,793
    VIEW DETAILS
  • 2026 Bennington 20SFSF

    2026 Bennington 20SFSF

    $47,510
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20' / 0'
    • 2026 / New
    • $47,510

    If your perfect Saturday involves a dawn patrol for bass and a sunset cruise with the crew, the Bennington 20 S 4 Point Fishing is your new best friend. This vessel is the ultimate... View Details

    View 23 Photos and Details Contact Seller
    $47,510
    VIEW DETAILS
  • 2026 Bennington 21SFCSF

    2026 Bennington 21SFCSF

    $56,802
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $56,802

    Step aboard the Bennington 21SFCSF, the ultimate party-and-pontoon-fishing hybrid! This is the boat for the family or friend group that can never quite agree on the day's activ... View Details

    View 18 Photos and Details Contact Seller
    $56,802
    VIEW DETAILS
  • 2026 Bennington 22SSRSE

    2026 Bennington 22SSRSE

    $59,930
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $59,930

    If you're seeking the ultimate on-water escape, look no further than this Bennington beauty. This vessel is perfectly designed for those who love to gather friends and family f... View Details

    View 19 Photos and Details Contact Seller
    $59,930
    VIEW DETAILS
  • 2026 Bennington 21SLSF

    2026 Bennington 21SLSF

    $61,954
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $61,954

    If your ideal weekend involves a seamless blend of adrenaline and pure relaxation, this 21 S Cruise is your match. Dressed to impress in Luminous Blue with sleek Matte Black accent... View Details

    View 21 Photos and Details Contact Seller
    $61,954
    VIEW DETAILS
  • 2026 Bennington 21SSB

    2026 Bennington 21SSB

    $69,072
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $69,072

    If you’re the kind of person who believes a Saturday isn't complete without a sun-soaked gathering, the Bennington 21SSB is your new best friend. This pontoon is a social butte... View Details

    View 22 Photos and Details Contact Seller
    $69,072
    VIEW DETAILS
  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    $69,210
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $69,210

    For the angler who refuses to choose between a serious fishing trip and a lively social hour, the Bennington 21SFC is the ultimate multipurpose escape. This isn't just a pontoo... View Details

    View 23 Photos and Details Contact Seller
    $69,210
    VIEW DETAILS
  • 2025 Starcraft SLS-3 Q

    2025 Starcraft SLS-3 Q

    $69,974
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 24' / 0'
    • 2025 / New
    • $69,974

    The Starcraft SLS3 Q Tritoon, available at Bluewater Marine in Port Orange, is a luxury performance machine designed to elevate your time on the water. This 3-tube tritoon offers a... View Details

    View 30 Photos and Details Contact Seller
    $69,974
    VIEW DETAILS
  • 2026 Bennington 22SSBSF

    2026 Bennington 22SSBSF

    $74,452
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $74,452

    Step aboard the Bennington 22 S Swingback and you will immediately notice that this is a craft built for the ultimate socialite. If you are the person who loves being the "hos... View Details

    View 20 Photos and Details Contact Seller
    $74,452
    VIEW DETAILS
  • 2026 Bennington 26MSLSF

    2026 Bennington 26MSLSF

    $175,714
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 28' / 0'
    • 2026 / New
    • $175,714

    Imagine the ultimate social hub that doesn't just sit on the water—it commands it. This Bennington 26 M Stern Lounge is the dream vessel for the consummate host who believes th... View Details

    View 24 Photos and Details Contact Seller
    $175,714
    VIEW DETAILS
  • 2026 Bennington 22SSSE

    2026 Bennington 22SSSE

    $64,972
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $64,972

    Step aboard the Bennington 22 S Stern Fishing boat, an ideal choice for anyone who loves spending time on the water, whether it's for serious angling or just cruising with love... View Details

    View 22 Photos and Details Contact Seller
    $64,972
    VIEW DETAILS
  • 2026 Bennington 20SL

    2026 Bennington 20SL

    $59,378
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20' / 0'
    • 2026 / New
    • $59,378

    Imagine a Saturday where the hardest decision you have to make is whether to lounge on the sunpad or take another lap around the lake. The Bennington 20SL is the ultimate "yes... View Details

    View 1 Photo and Details Contact Seller
    $59,378
    VIEW DETAILS
  • Price Drop 2022 Cypress Cay 232 Seabreeze

    2022 Cypress Cay 232 Seabreeze

    $22,720
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 24' / 0'
    • 2022 / Used
    • $22,720

    The Cypress Cay 232 Seabreeze is the perfect choice of ponbtoon boat for you and up to 11 family & friends to cruise the waterways creating life long memories. View Details

    View 8 Photos and Details Contact Seller
    $22,720
    VIEW DETAILS
  • Price Drop 2022 Cypress Cay 232 Seabreeze

    2022 Cypress Cay 232 Seabreeze

    $22,720
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2022 / Used
    • $22,720

    Confidence comes from intuitive ease of use, reliability and safety. The Seabreeze 232 packs those features and more on a 23-foot pontoon platform. The single-piece fiberglass helm... View Details

    View 8 Photos and Details Contact Seller
    $22,720
    VIEW DETAILS
  • Price Drop 2022 Godfrey Sweetwater 2286

    2022 Godfrey Sweetwater 2286

    $34,900
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2022 / Used
    • $34,900

    Put down the welcome mat and kick off your shoes, there’s just something about a Sweetwater Cruise that feels right. With nearly unlimited customization options, you'll feel right... View Details

    View 9 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • 2025 Veranda VX27DCRC

    2025 Veranda VX27DCRC

    $149,334
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 29' / 0'
    • 2025 / Used
    • $149,334

    Beautiful 2025 DEMO model Veranda VX27DCRC powered by a Mercury 500 Racing Outboard! Factory Warranty! DEMO MODEL: VX27DCRC Triple Toon 27" High HP Flooring - Woven Pewter Rail Col... View Details

    View 10 Photos and Details Contact Seller
    $149,334
    VIEW DETAILS
  • 2022 Godfrey Sweetwater 2286

    2022 Godfrey Sweetwater 2286

    $32,705
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2022 / Used
    • $32,705

    The Sweetwater 2286 is the perfect choice of vessel for up to 12 friends and family to spend a lazy day on the river, creating life-long memories. View Details

    View 10 Photos and Details Contact Seller
    $32,705
    VIEW DETAILS
  • 2022 Godfrey Sweetwater

    2022 Godfrey Sweetwater

    $29,293
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2022 / Used
    • $29,293

    This 2022 Godfrey Sweetwater 2286 is nearly 23 feet in overall length and crafted with a durable aluminum hull and is perfect for leisurely outings on the water or a day of fishing... View Details

    View 10 Photos and Details Contact Seller
    $29,293
    VIEW DETAILS
  • 2022 Cypress Cay Seabreeze 232

    2022 Cypress Cay Seabreeze 232

    $29,500
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2022 / Used
    • $29,500

    The Cypress Cay Seabreeze 232 is an ideal family boat that accommodates up to 12 passengers, perfect for lakes and rivers. It excels in leisurely cruising, fishing, and entertainin... View Details

    View 10 Photos and Details Contact Seller
    $29,500
    VIEW DETAILS
  • 2021 Godfrey Sweetwater 2286

    2021 Godfrey Sweetwater 2286

    $29,753
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 23' / 0'
    • 2021 / Used
    • $29,753

    This 2022 Godfrey Sweetwater 2286 is nearly 23 feet in overall length and crafted with a durable aluminum hull and is perfect for leisurely outings on the water or a day of fishing... View Details

    View 10 Photos and Details Contact Seller
    $29,753
    VIEW DETAILS
  • 2023 Other Select 322 CC

    2023 Other Select 322 CC

    $29,410
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 22' / 0'
    • 2023 / Used
    • $29,410

    The Suncatcher G3 is known for affordability and quality. This saltwater ready pontoon boat features a center console and 150 hp Yamaha outboard. Perfect for fishing with room for... View Details

    View 10 Photos and Details Contact Seller
    $29,410
    VIEW DETAILS
Showing 64 to 84 of 229 boats found.
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Pontoon Boats on Boatcrazy

Pontoon boats are an exceptionally customizable boat type that can provide for a wide variety of boating activities. Often these boats are configured with a large flat deck that rests on multiple pontoons.

Pontoons are usually very spacious and allow for passengers to move about quite a bit. Some pontoons come with powerful outboard motors which can handle towing tubes and wake surfers.

Pontoon Boats manufacturers on Boatcrazy

When looking to buy a quality Pontoon boat, consider these top Pontoon Manufacturers

Harris, Bennington, Manitou, Barletta, Godfrey, Sun Tracker, G3, Fun Country and Avalon.

Pontoon Boats For Sale by State

Pontoon Boats Frequently Asked Questions

How fast will a 20 foot Pontoon boat go?

On average, a 20ft Pontoon boat will reach speeds of around 23mph. Pontoons 20 to 22-foot, are well suited for lakes and rivers that do not have large waves.

Mid-sized boats are well equipped to seat up to 13 passengers. The larger 23 to 28-foot boats are capable of cruising through rough waters and offer enough space for up to 15 people to enjoy a day on the lake.

For beginners, towing a Pontoon boat for the first time can be a very daunting experience, but actually loading and towing your pontoon boat onto the correct trailer and accessories can be fairly easy. Ensure you move it to shallower waters first before attempting to load.

There is no magical time to buy a Pontoon boat, as we always have plenty of listings all year round. But winter seems to be a better time to buy a pontoon boat, as this is the season when many boat shows are held. During this period, boat dealers tend to go to great lengths to come up with the best deals to catch the attention of people who watch the shows.

A Pontoon boat mpg will vary depending on the weather and conditions, but 3.5 miles per gallon is not too far from average. Weight and specifications also play a part on fuel consumption.

The average cost of a new pontoon boat ranges from $15,000 to upwards of $175,000. The price will vary greatly depending on factors like size and accessories. Obviously, buying a new pontoon boat instead of a used version does carry a significantly higher price tag, but it will come with a full warranty. You can also get a good deal on used Pontoons though, and there are plenty for sale on Boatcrazy, for as little as $5,000 you can start having fun on the water!