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    Sheboygan, Wisconsin Boat Rentals

    Page 1 of 1 • 24 listings

    Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.
    Fishing in Two Rivers · 6 guests

    Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.

    New
    $130/hour
    Tritoon for rent in Oshkosh!dsd
    Powerboats in Oshkosh · 13 guests

    Tritoon for rent in Oshkosh!dsd

    4.9
    $125/hour
    Fish n Cruise Pontoon in the Winnebago system
    Powerboats in Oshkosh · 11 guests

    Fish n Cruise Pontoon in the Winnebago system

    5.0
    Superowner
    Best of 2025
    $400/day
    48ft Regal Commodore for rent in Milwaukee
    Events in Milwaukee · 12 guests

    48ft Regal Commodore for rent in Milwaukee

    5.0
    $325/hour
    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
    Sailing in Milwaukee · 6 guests

    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

    New
    $120/hour
    12 Person, 24 Foot Robalo on Lake Michigan, with bathroom!
    Powerboats in Milwaukee · 12 guests

    12 Person, 24 Foot Robalo on Lake Michigan, with bathroom!

    5.0
    $115+/hour
    13 Person 26ft Chaparral Powerboat on Lake Michigan with a Bathroom!
    Powerboats in Milwaukee · 13 guests

    13 Person 26ft Chaparral Powerboat on Lake Michigan with a Bathroom!

    5.0
    $110+/hour
    Fully Rigged Fishing Boat on Lake Michigan!
    Powerboats in Milwaukee · 12 guests

    Fully Rigged Fishing Boat on Lake Michigan!

    New
    $115/hour
    Charter this beautiful Catalina from Milwaukee, WI - Captain Included
    Sailing in Milwaukee · 6 guests

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    5.0
    $150/hour
    25' Avalon Luxury Pontoon Rental in Milwaukee
    Powerboats in Milwaukee · 10 guests

    25' Avalon Luxury Pontoon Rental in Milwaukee

    5.0
    Superowner
    $150/hour
    23' Godfrey Luxury Pontoon in Milwaukee
    Powerboats in Milwaukee · 10 guests

    23' Godfrey Luxury Pontoon in Milwaukee

    5.0
    Superowner
    $150/hour
    Luxury Pontoon Boat Ride Along the Milwaukee River
    Powerboats in Milwaukee · 10 guests

    Luxury Pontoon Boat Ride Along the Milwaukee River

    5.0
    $150/hour
    FourWinns Luxury Speed Boat available for Events, Date Nights and Family Outings
    Powerboats in Milwaukee · 6 guests

    FourWinns Luxury Speed Boat available for Events, Date Nights and Family Outings

    5.0
    Superowner
    $150/hour
    Manitou 23ft Pontoon on the Milwaukee River
    Powerboats in Milwaukee · 10 guests

    Manitou 23ft Pontoon on the Milwaukee River

    5.0
    $150/hour
    Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!
    Events in Milwaukee · 30 guests

    Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!

    New
    $500/hour
    Captained Charter 30' Sailboat in Milwaukee, Wisconsin
    Sailing in Milwaukee · 6 guests

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    5.0
    Snoozed - Active 02 Jan 2026
    21ft SeaRay SunDeck for Pewaukee Lake. Other lakes by request.
    Powerboats in Pewaukee · 8 guests

    21ft SeaRay SunDeck for Pewaukee Lake. Other lakes by request.

    5.0
    $155/hour
    Instant Book
    Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin
    Fishing in Algoma · 6 guests

    Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin

    New
    $113+/hour
    Experience the Thrill - Sea-Doo GTX
    Water Sports in Wisconsin · 3 guests

    Experience the Thrill - Sea-Doo GTX

    New
    Snoozed - Active 02 Aug 2025
    2 Kayaks for rent Jefferson WI
    Adventures in Wisconsin · 1 guest

    2 Kayaks for rent Jefferson WI

    New
    $60/day
    One of the BEST Surf/Wake Boats in Fremont!!
    Powerboats in Fremont · 10 guests

    One of the BEST Surf/Wake Boats in Fremont!!

    5.0
    $150/hour
    Lake Tichigan Pontoon Boat Waterford (30 mins from MKE), no tubing, min 3hrs
    Powerboats in Wisconsin · 10 guests

    Lake Tichigan Pontoon Boat Waterford (30 mins from MKE), no tubing, min 3hrs

    5.0
    $70/hour
    Sail Lake Michigan from Racine, WI
    Sailing in Racine · 6 guests

    Sail Lake Michigan from Racine, WI

    5.0
    $75/hour
    19ft Proline Boat Rental in Racine, Wisconsin
    Powerboats in Racine · 4 guests

    19ft Proline Boat Rental in Racine, Wisconsin

    New
    $125/hour

    Sheboygan Reviews

    1. TC

      Tom

      Manitou 23ft Pontoon on the Milwaukee River

      Ryan provided an excellent tour of the Milwaukee river. He’s very personable and informative and my crew thoroughly enjoyed themselves. I highly recommend him as a captain, we will definitely hire him the next time we’re in town.

    2. DT

      David

      25' Avalon Luxury Pontoon Rental in Milwaukee

      Fantastic trip with Captain Coran - very informative on the Milwaukee River front- would highly recommend for anyone wanting a enjoyable experience in Milwaukee

    3. BW

      Betty

      Fish n Cruise Pontoon in the Winnebago system

      Great boat, lots of room. Josh is very easy to communicate with and great at accommodating whatever you might need.

    4. Brooke

      Brooke

      Fish n Cruise Pontoon in the Winnebago system

      Great time on the pontoon , comfortable and easy in and out of slip! Perfect for bonding with friends and family in a comfortable setting

    5. TC

      Terry

      25' Avalon Luxury Pontoon Rental in Milwaukee

      Coran was fantastic! We will definitely be sailing the open sea with him again!

    6. RH

      Robbie

      Fish n Cruise Pontoon in the Winnebago system

      Fantastic boat and experience. Will be a repeat customer in the future!

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