Roll With it Rentals is now accepting all High Season reservations of one full week or greater and all Low Season reservations of a 5 day minimum via the online reservation system.

All High Season (June 15th - September 15th) short-term reservations less than the required full week, but 4 days or greater, must be booked within 1 month of your departure date.

All short-term reservations are subject to a $49.00 maintenance fee.

Roll With it Rentals requires a 20% Non-Refundable deposit in order to secure a Booking.

Please contact Todd at (204) 981-0902 to book a short-term reservation.


Legal Stuff


For any questions, please contact us and we’d be happy to answer them.

  • Rental of the trailer is for the agreed time only and must be paid in full prior to rental pick-up. While every effort will be made to accommodate extensions, Roll With it Rentals cannot guarantee an extenuation will be achieved. Late return of the trailer will result in potential loss of performance/damage deposit.
  • To reserve a trailer: Roll With it Rentals inc. requires a Non-refundable performance deposit of an amount equal to 20% of the total rental amount and a $500.00 Damage deposit (payable by Credit Card at time of Pick up). Roll With it Rentals will hold the Damage deposit until inspection of the rental unit has been completed. Once the rental has been returned in satisfactory condition, the Damage deposit for $500.00 shall be returned to the renter.
  • Before hire, all equipment is cleaned and maintained to our schedule and must be returned in like condition. Failure to do so may result in potential loss of damage/performance deposit.
  • The undersigned renter accepts all responsibility for all violations and infractions under the highway and traffic act while the above mentioned vehicle is under their control. 
  • Roll With it Rentals hereby acknowledges and gives full authorization to the above mentioned renters to travel into the United States of America with the indicated rental trailer for the agreed upon duration.