Id call the owner and ask them to measure from the front wheel up against a wall to the center of the rear axle. If that measurement is the same as the length of your shortbed, you will be okay. However, I think that has a fat chance of fitting... It might, however, go in at an angle, rather than straight in...but it is never as sturdy and stable as when you tie it down properly when it is perpendicular.
I too would probably rent a U-Haul trailer. Me and my friends used to rent the garden trailers from them - fold down gate that you can use as a ramp, and its got a hundred places to use as tie-down spots. Not sure how that would handle snow though!
2003 Vegas - straight pipes, Big Sucker air filter kit, black powder coated everything - foot controls, handlebars, clutch and brake housing, fork lowers, luggage rack, wheels, digital speedo with powder coated housing. Relocated key switch, red plug wires. Mustang solo seat. LED ring blinkers in front. Black DEI pipe wrap.