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We are finally nearly all booked - still need 2 bed condo in Waikiki

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With all your help,lots of googling and reading + searching the travel forums we now have a great holiday planned for our family of 4 with (17 and 19 yo young adults) for December.....now the long wait! I definitely have Hawaii fever the worst in my family and have to be careful how much I bring up the topic at home :-). All the reading and lovely stories from other fodorites makes this place such an exciting holiday destination. Thank you!
We will have 6 days first in Waikiki 1st week of December then off to Maui (Wailea) 8nights, Big Island Hali'i Kai Waikola 8nights, Christmas in Kauai Poipu Beach 8 nights and one night back in Waikiki before we fly home to Aus on NYE.
We plan to rent a car in Maui,B.I and Kauai.
I have seen a 2 bed condo at Aston Waikiki Beach tower through VRBO I like - any thoughts on this location/ any other ideas? - Would like something no more than $400-450/night and definitely min 2 bedroom. We really won't do the '2 rooms at a hotel' option.
This Waikiki part of our trip will be in the 1st week of Dec - is it as urgent to book that now / could I wait until May? The exciting news is I am now going to Waikiki with my husband in May for 1 week with his work so I could do a little 'real life' investigating whilst I was there???
Many thanks for any input you can offer.

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