I am new to this post, so please bear with me.

My family & I are planning a trip in June to Hawaii. Our plans are to arrive June 25 & stay for 4 nites in Oahu (Waikiki) & then go to Maui for the remaining 6. My problem arises when I start to look for hotels in Maui. I have researched this forum extensively & have a definite top 5 for Maui hotels, but they are VERY expensive. Is it wise to wait until closer to our date to start booking a hotel? I want to book the Sheraton Maui, but the cost now is $400 per night (ocean view). Will this price increase or decrease closer to our arrival date.

I think I've pretty much decided on the Hilton Hawaiian Village for Waikiki (around $235 per nite). There are 4 of us traveling. Husband & me (mid 30's), 13 year old, 2 year old & 56 year old physically active grandmother. We want to stay in a place that is fun for kids, upper scale & below $300 in Maui.

Any advice out there?

If you join the Sheraton Perferred Guest program (available at starwood.com) you often can get 30% off room rates at all Sheratons. The Hawaii special seems to be offered pretty much all the time.

You can also make reservations at any hotel and just call and cancel if better rates become available. So, if you are sure where you'd like to stay why not get the reservation set and change if something better comes along.

Ok, happy to "help" but "56 year old physically active grandmother"?? I have good friend who is a 65 year old father of an 18 year old. No one would question whether he's "physically active" at 65! Hey- it's the 2000's!!!
Now- I travel to Hawaii every summer and have for many years with my kids (despite my elderly age- 49). I have also worked in the travel industry for over 25 years. Every summer I deal with last minute Hawaii travellers who have far smaller numbers of options due to their late booking. I book my property on Kauai before I leave each year- for the next year. You will not find anything less expensive if you wait unless there are very unusual circumstances in Hawaii next year. Have you considered a condo in Maui? There are some very good choices in Napili for a group such as yours. It would make a lot of sense from many stand points. I'd look into Napili Kai or- for budget- Napili Surf.
Good luck with grandma!

devonne, I count 5 (you and your husband, 2 kids, grandma), and with that many people I agree that your money will go a lot farther if you get a condo. All of the upscale condos will have daily maid service, restaurants on the property, and kid-oriented activities, so it's very much like staying at a hotel but you'll have a full kitchen. Think breakfast on the lanai...and somewhere to keep juice and snacks for the 2 year old.

I agree that you should look into condos. You would have multiple baths and a full kitchen for snacks and breakfasts and many have washers and dryers in the unit, some for less $ than a hotel room. Check out vrbo.com which lists condos you can rent directly from owners and cut out the middle man's $$. Good luck.