The wiki on the 1935 Labour Day Hurricane is good. It was marked by controversy over the deaths of many WWI veterans, many of whom had what we would call PTSD and were struggling to cope with life. They frequently would get into brawls on pay day and were generally regarded poorly by the State.
Back in 1935 of course there were few warnings with no satellites. They knew the storm was coming because of its passage through the Caribbean but did nothing.
One of the people who would have been responsible for evacuation was on holiday and the long term strategic plan to evacuate by train had a major flaw because there was a misunderstanding. The authorities though that should one be needed it could just be sent but the reality was it need a couple of hours preparation before it could depart.
By the time the order to evacuate was given it was too late. The train got there and picked up vets as the storm was already approaching. The carriages were blown off the track and only the locomotive (which was heavier) remained on the track.
en.wikipedia.org/wiki/1935_Labor_Day_hurricane
There are a couple of other interesting facts in this. Firstly it followed a course very similar to the one Irma is tracking. It was one of only three cat 5s to hit the US in the 20th Century (Andrew in 1992 and Camille in 1969 are the other two). So as far as comparisons go, its about as close as we have within recorded memory.
Secondly the hurricane was written about by Ernest Hemingway. He had ridden the storm out at his home in Key West. The house is now a cat sanctuary and there are 10 people staying at the sanctuary to look after the animals. It was built in 1851 and has survived two centuries of storms. It stands at 16ft above sea level and is one of the highest points in the Keys. If you were going to ride it out, its probably where you'd choose. The problem? The prediction are for up to 20ft storm surges.
Thirdly, the Labour Day Hurricane was much smaller than Irma. Its eye was Its eye was eight miles across and the fiercest winds extended 15miles off the center, making it smaller than Hurricane Andrew.
Of course neither the Keys nor Tampa were as populated and built up in 1935.
But as I say as a historical reference point this is the closest there is.
The Labour Day Hurricane remains the one with the lowest pressure and highest winds recorded in the US.