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Hawaii - Advice on Rentals vs Hotels for Oct 2014

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Plan on visiting Hawaii for 3+ weeks this October, visiting 2-3 islands and staying 1 week per island. No set itinerary yet, but do plan on staying in 1 place per island, and doing doing day trips from that base. The only place I know I wont be staying (may visit but not spending an evening) is Honolulu.
I don't need beach front. I've never been there before and know the prices are steep, but is it reasonable to think 2 people could rent a place for $200/day or perhaps $1,200/week? Would that get us at least a 3 star hotel, or a small condo or apartment unit?
What site is the best to use for looking up places? Booking.com, Travelocity, VBRO, etc.
Thank you

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