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    The Best Sailboat Rentals Near Oakville

    Browse, book, and get out onto the water with local captains and boat owners.

      Our Favorite Sailboat Rentals Near Oakville

      4.9 (4,396 reviews)

      •

      • Hunter 43 Sailing Yacht in Oakville, Ontario
        Sailing in Oakville · 5 guests

        Hunter 43 Sailing Yacht in Oakville, Ontario

        5.0
        $270/hour
      • 35ft C&C 35 Sailboat in Toronto
        Sailing in Etobicoke · 6 guests

        35ft C&C 35 Sailboat in Toronto

        5.0
        $180/hour
      • 27 Foot Sailboat for a Day of Fun in the Sun in Toronto
        Sailing in Toronto · 6 guests

        27 Foot Sailboat for a Day of Fun in the Sun in Toronto

        5.0
        $54/person
      • Sail in downtown Toronto
        Sailing in Toronto · 6 guests

        Sail in downtown Toronto

        5.0
        $72/person
      • 28' Sailboat for 5 guests in Toronto
        Sailing in Toronto · 5 guests

        28' Sailboat for 5 guests in Toronto

        New
        $235/hour
      • 38' Sailing Yacht in Toronto, Ontario
        Sailing in Toronto · 8 guests

        38' Sailing Yacht in Toronto, Ontario

        New
        $400/hour
      • Fountain Pajot Astrea Luxury 42' Catamaran for Charter
        Sailing in Toronto · 18 guests

        Fountain Pajot Astrea Luxury 42' Catamaran for Charter

        5.0
        $1,100+/hour
      • 41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
        Sailing in Toronto · 12 guests

        41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

        New
        $435/hour
      • Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!
        Events in Toronto · 15 guests

        Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!

        5.0
        $359/hour
      • Beautiful Trimaran for 10 People in Toronto
        Sailing in Toronto · 12 guests

        Beautiful Trimaran for 10 People in Toronto

        5.0
        $288/hour
      • A Tropical Experience on a Massive Sailing Trimaran
        Sailing in Toronto · 12 guests

        A Tropical Experience on a Massive Sailing Trimaran

        4.9
        $324/hour
      • The Twilight Tour on 35ft Hughes Sailboat
        Sailing in Toronto · 2 guests

        The Twilight Tour on 35ft Hughes Sailboat

        New
        $108/hour
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      This weekend$100-$300 trips2-4 peopleCaptained

      Types of Boats Popular in Oakville

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      Top Sailboat Rental Locations Near Oakville

      Most Popular Yacht Rentals in Oakville

      • Luxury 50ft Private Yacht Cruise from Downtown
        Events in Toronto · 20 guests

        Luxury 50ft Private Yacht Cruise from Downtown

        5.0
        Superowner
        $324/hour
      • 44' Luxury Double Decker in Toronto for any Occasion / Event
        Events in Toronto · 20 guests

        44' Luxury Double Decker in Toronto for any Occasion / Event

        4.9
        Best of 2023
        $180/hour
      • Experience an Unforgettable Party on Toronto's 34ft Yacht Capacity for 8 Guests
        Events in Toronto · 8 guests

        Experience an Unforgettable Party on Toronto's 34ft Yacht Capacity for 8 Guests

        5.0
        Superowner
        Best of 2023
        $111/hour
      • Enjoy Toronto in 41' Motor Yacht! (Mon To Thurs $300/hour)
        Events in Toronto · 12 guests

        Enjoy Toronto in 41' Motor Yacht! (Mon To Thurs $300/hour)

        5.0
        Superowner
        $288/hour
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      Most Popular Jet Ski Rentals in Oakville

      • 2024 Seadoo Rental in Mississauga, Ontario
        Water Sports in Mississauga · 3 guests

        2024 Seadoo Rental in Mississauga, Ontario

        5.0
        $73/hour
      • Seadoo GTX 300 limited Jetski Rental in Toronto, Ontario
        Water Sports in Toronto · 3 guests

        Seadoo GTX 300 limited Jetski Rental in Toronto, Ontario

        5.0
        $129/hour
      • Seadoo 2023 JetSki GTX 170 in Mississauga, Ontario
        Water Sports in Mississauga · 2 guests

        Seadoo 2023 JetSki GTX 170 in Mississauga, Ontario

        New
        $288+/day
      • Brand New Sea Doo GTI 130 SE Jet Ski for rent in Toronto
        Water Sports in Scarborough · 2 guests

        Brand New Sea Doo GTI 130 SE Jet Ski for rent in Toronto

        5.0
        $101/hour
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      Most Popular Boat Tours in Oakville

      • Torontos Premier 44-Foot Double-Decker Yacht
        Events in Toronto · 12 guests

        Torontos Premier 44-Foot Double-Decker Yacht

        New
        $431/hour
      • SeaRay Sundancer 36ft Captained Yacht Charter in Toronto!
        Events in Etobicoke · 10 guests

        SeaRay Sundancer 36ft Captained Yacht Charter in Toronto!

        New
        $198/hour
      • 45 Foot Luxurious Yacht Charter - Ask about end of the season special.
        Events in Toronto · 12 guests

        45 Foot Luxurious Yacht Charter - Ask about end of the season special.

        5.0
        Superowner
        Best of 2023
        $216/hour
      • Cruise in style in a 45' Yacht DT Toronto
        Events in Toronto · 14 guests

        Cruise in style in a 45' Yacht DT Toronto

        New
        $288/hour
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      Recent Reviews in Oakville

      Top Sailboat Rental Locations in Canada

      How To Book on Getmyboat

      4.9 out of 5! • 500,000+ reviews
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        Browse

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        Inquire & Book

        Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

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        Enjoy

        Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

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