I dought it, Maybe backwards with the ski's out. Modern snowmobiles (polaris anyway) are 48" on center ski to ski. IIRC the Stebside box is 48" inside dimensions so it would be two skinney by abou 4-6". Not to mention putting a modern sled in a pickup box sucks! Buy a cheap steel trailer, they are only 500 bucks new, they won't last long but they'll get you through a few winters.