Should I Book Hotels Thru Net Early In Waikiki?

I am planning of travelling to Honolulu in September and planning to stay in Waikiki for 10 days.
September shouldnt be high season for Hawaii right?
Should I book the hotels in advance or wait until closer date for last minute book in the internet?
Would it make it cheaper? or I would be missing special deals (like 5th nite free) and jeorpadise the availability and perhaps price??
Need some advice please? Thanks!
NB: I am on a budget – so probably wont spend more than $150/night. The cheaper the better! ;-)
Also, considering some hotel is not what the picture looks like, I am thinking maybe I should just book for 1 nights, then I can see the hotel condition when I get there.
What do you think?

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