The objects that I had that were bigger than a single tile were broken up into multiple tiles. By doing this I was able to create the illusion of depth by drawing them on different layers relative to the player so the 'front' were rendered behind the player while the 'back' was rendered in front of the player.

But, back to your question... how could this work if the objects are bigger than a tile? Good question

I'm not sure and it's not a solution I would pursue personally because of the overheads involved.