As of Aug 30th, 2014, the Shingle Creek Regional Park at Steffee Landing (across the creek from Steffee Homestead) has canoes and kayaks for rental.
Some of my friends and I took a nice trip south down the creek. You can go about 2 miles, for a round trip of 4 miles, before it becomes a bit too difficult for the canoes or multi-person kayaks to fit through.
According to a couple we met there, you can in fact make it about 0.8 miles from Old Tampa Highway before you cant go any further. We went about 0.5 mile north as well before heading back.
The north side is wide, slow moving and deep. There isn’t any shade though. Just something to keep in mind. There are places to port and get out of the boats heading in both directions.
Thanks to Dylan for sharing this about Shingle Creek! We drove over it a couple of weeks ago on the Old Tampa Highway and were wondering how far you could get in a kayak or canoe.