• Boats
  • Bennington
    Within 100 Miles Of
    Fleming Island, Florida

Filter Boats By

Filters

from

Boat Make / Model

Bennington boats for sale in Fleming Island Florida

There are 21 new and used Bennington boats for sale in Fleming Island, Florida. Browse Bennington boat types like Pontoon on BoatCrazy. View a wide selection of Bennington boats from $26,500 to $169,714.
Fleming Island, Florida Boats For Sale
  • Back
  • Boats
  • Bennington
    Within 100 Miles Of
    Fleming Island, Florida
21 boats found within 100 miles from Fleming Island, Florida
Back
Filter
  • Price Drop 2026 Bennington 21 S Fishing

    2026 Bennington 21 S Fishing

    $59,974
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $59,974

    Cast a line into a world where catching the "big one" doesn't mean sacrificing an ounce of style. This Bennington 21 SF is a masterclass in versatility, blending a se... View Details

    View 21 Photos and Details Contact Seller
    $59,974
    VIEW DETAILS
  • Price Drop 2026 Bennington 26 M STERN LOUNGE

    2026 Bennington 26 M STERN LOUNGE

    $167,701
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 25'
    • 2026 / New
    • $167,701

    Imagine a sunset cruise where the conversation flows as effortlessly as the water beneath you. The M Series Stern Lounge is the ultimate sanctuary for social butterflies and relaxa... View Details

    View 26 Photos and Details Contact Seller
    $167,701
    VIEW DETAILS
  • 2026 Bennington 20 S CRUISE

    2026 Bennington 20 S CRUISE

    $56,737
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2026 / New
    • $56,737

    Ready to swap the daily grind for some serious sunshine? The Bennington 20SL is the ultimate ticket to a permanent vacation. This boat is a social butterfly’s dream, designed for t... View Details

    View 17 Photos and Details Contact Seller
    $56,737
    VIEW DETAILS
  • Price Drop 2026 Bennington 21 S FISH AND CRUISE

    2026 Bennington 21 S FISH AND CRUISE

    $59,631
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $59,631

    For the "pro-social" angler who refuses to choose between a serious morning catch and a premium afternoon lounge, the Bennington 21SFC is your ultimate dual-threat. This... View Details

    View 19 Photos and Details Contact Seller
    $59,631
    VIEW DETAILS
  • Price Drop 2026 Bennington 22 S SWINGBACK

    2026 Bennington 22 S SWINGBACK

    $79,917
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2026 / New
    • $79,917

    Ready to elevate your weekend hosting game? The Bennington 22SSB is a social butterfly’s dream, trading traditional layouts for an ultra-versatile Swingback stern lounger. Whether... View Details

    View 18 Photos and Details Contact Seller
    $79,917
    VIEW DETAILS
  • Price Drop 2026 Bennington 24 M STERN LOUNGE

    2026 Bennington 24 M STERN LOUNGE

    $127,833
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 26'
    • 2026 / New
    • $127,833

    If your idea of a perfect weekend involves a high-energy social gathering that seamlessly transitions into a sun-drenched evening cruise, this specific Bennington 24MSL is your ult... View Details

    View 23 Photos and Details Contact Seller
    $127,833
    VIEW DETAILS
  • Price Drop 2026 Bennington 18 S Fish and Cruise

    2026 Bennington 18 S Fish and Cruise

    $39,792
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 19'
    • 2026 / New
    • $39,792

    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
    $39,792
    VIEW DETAILS
  • 2026 Bennington 22 S Stern Radius

    2026 Bennington 22 S Stern Radius

    $79,910
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $79,910

    Ready to trade the shore for the horizon? The Bennington 22 S Stern Radius is your ultimate ticket to effortless lake days. This isn't just a boat; it’s a floating social hub d... View Details

    View 22 Photos and Details Contact Seller
    $79,910
    VIEW DETAILS
  • 2024 Bennington 20 SVL

    2024 Bennington 20 SVL

    $39,761
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2024 / Used
    • $39,761

    Ready for the ultimate weekend escape with zero compromises? The 2024 Bennington 20 SVL is a masterclass in elegant, comfortable pontoon cruising designed to elevate your family do... View Details

    View 12 Photos and Details Contact Seller
    $39,761
    VIEW DETAILS
  • 2020 Bennington 25 SSRDN

    2020 Bennington 25 SSRDN

    $49,900
    Saint Augustine, FL
    • Saint Augustine, FL
    • Pontoon
    • 25'
    • 2020 / Used
    • $49,900

    FOR QUESTIONS CONTACT: ROBERT 202-243-8218 or rwrosso71@gmail.com2020 Bennington 25SSRDN - Saltwater Series - TritoonIncludes an EZ Loader Trailer and various transferrable warrant... View Details

    View 15 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • Price Drop 2026 Bennington 22 S 4 PT FISHING

    2026 Bennington 22 S 4 PT FISHING

    $64,971
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2026 / New
    • $64,971

    The Bennington 22SF is the ultimate "choose your own adventure" vessel, perfectly blurring the lines between a serious angling machine and a high-end entertainment lounge... View Details

    View 21 Photos and Details Contact Seller
    $64,971
    VIEW DETAILS
  • Price Drop 2026 Bennington 20 S CRUISE

    2026 Bennington 20 S CRUISE

    $58,971
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20'
    • 2026 / New
    • $58,971

    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 19 Photos and Details Contact Seller
    $58,971
    VIEW DETAILS
  • Price Drop 2026 Bennington 26 M STERN LOUNGE

    2026 Bennington 26 M STERN LOUNGE

    $169,714
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 28'
    • 2026 / New
    • $169,714

    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
    $169,714
    VIEW DETAILS
  • Price Drop 2026 Bennington 22 S STERN RADIUS

    2026 Bennington 22 S STERN RADIUS

    $77,691
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2026 / New
    • $77,691

    The Bennington 22SSR is the ultimate companion for the social butterfly who believes the best days are spent surrounded by friends and family. This pontoon is masterfully designed... View Details

    View 24 Photos and Details Contact Seller
    $77,691
    VIEW DETAILS
  • Price Drop 2026 Bennington 22 S Swingback

    2026 Bennington 22 S Swingback

    $69,791
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2026 / New
    • $69,791

    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
    $69,791
    VIEW DETAILS
  • Price Drop 2026 Bennington 21 S FISH AND CRUISE

    2026 Bennington 21 S FISH AND CRUISE

    $67,973
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $67,973

    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
    $67,973
    VIEW DETAILS
  • Price Drop 2026 Bennington 21 S SWINGBACK

    2026 Bennington 21 S SWINGBACK

    $68,472
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $68,472

    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
    $68,472
    VIEW DETAILS
  • Price Drop 2026 Bennington 21 S Cruise

    2026 Bennington 21 S Cruise

    $59,754
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $59,754

    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
    $59,754
    VIEW DETAILS
  • Price Drop 2026 Bennington 21 S Fish and Cruise

    2026 Bennington 21 S Fish and Cruise

    $54,801
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $54,801

    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
    $54,801
    VIEW DETAILS
  • Price Drop 2026 Bennington 20 S Fishing

    2026 Bennington 20 S Fishing

    $39,971
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20'
    • 2026 / New
    • $39,971

    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
    $39,971
    VIEW DETAILS
  • 2016 Bennington 22 SSX

    2016 Bennington 22 SSX

    $26,500
    Mount Dora, FL
    • Mount Dora, FL
    • Pontoon
    • 22'
    • 2016 / Used
    • $26,500

    2016 Bennington 22 SSX with Yamaha 115 22' Pontoon This well-maintained 2016 Bennington 22 SSX offers the perfect blend of comfort, reliability, and performance. Powered by a... View Details

    View 17 Photos and Details Contact Seller
    $26,500
    VIEW DETAILS
Showing 1 to 21 of 21 boats found.

Bennington Boats For Sale By Model (by popularity)

Bennington Boats For Sale

New and Used Bennington Boats

Bennington Boats On Boatcrazy

Bennington, a luxurious line of Pontoon and Tritoon boats, is a company that sets the design trend exceeding the industry standard.

Founded in 1997 in Indiana, the company takes pride in using only the best materials and never cutting corners. With meticulous attention to detail and quality, Bennington is a leader in innovation and design for boating. Building their boats using a fully welded aluminum construction, Bennington pontoons are able to give you a safe and stable boating experience, and their Furniture is the perfect combination of comfort and support through their ergonomic design. With plenty of space and seating Bennington Pontoons are perfect for Fishing, Cruising and Entertaining.

Find your next Bennington boat on Boatcrazy.com

Bennington Boats Frequently Asked Questions

They have a good selection of models, options, and price points, depending on what model yo choose. They also have a lifetime structural and decking warranty on all their boats. You can view a wide selection of Bennington boats on Boatcrazy from $14,995 to $179,990.

Bennington's luxury Pontoon and Tritoon boats are known for their high-quality design and performance. Their Tritoons are able to handle rough and choppy waters because of the third toon. This helps to stabilize the boat and give a smoother ride.

Their extensive model series line-up is the Q, R, L, and S, Series. Some of the more popular models include; 23LSB, 20SLG, 21LL, and 21SXL.

Bennington pontoons are good for all water activities, day cruising on lakes and waterways, but they are also a great boat for fishing and even some water sports.