We've stayed at HHV 3 times since 2009 and are planning a 4th trip next September. We have not stayed at the Rainbow Tower since renovation, but the views of the ocean and Diamond Head more than made up for the need for sprucing up (the rooms in Rainbow are a bit smaller than others). You have to decide on your own whether having an ocean view is important. All of the rooms we've stayed in have been clean, comfortable and well-appointed. (We have not stayed in Diamond Head.) The property itself is clean and neat, the grounds are well-lit and secure, and they run the 'sandboni' every morning over the beach. The restaurants are hit and miss, with Round Table pizza being a hit. We were a bit disappointed with our last visit to the breakfast buffet at the Rainbow Tower. I hope it was just a 'bad buffet' day, because this was a culinary highlight of previous stays, although expensive.
There is a lot of action associated with HHV (and some interesting history). Last visit, we were there during the Pro Bowl and there was always something going on. The down side is when certain facilities close (like the big pool) to host these specials. Hawaii 5-0 was shooting by The Tropics one night. That was fun. The Friday night fireworks are spectacular.
You can book lots of trips and activities through the hotel. I highly recommend Huanama Bay snorkeling - and make sure you are on one of the first vans out in the morning. Less crowded, less murky water. You can depend on tours for sightseeing, but a rental car is nice. Hilton charges $27 a night to self-park, so be sure to budget for that. Don't forget to pay your respects at Pearl Harbor.
I would think any time is Hawaii time, but I prefer late November through February. For one thing, the tides are higher at the North Shore (better for catching the waves with board or camera). If you are into whale watching, you are more likely to see them in the winter months. If you take a whale-watching cruise, book it early enough in your stay that if you do not see any, you can take advantage of a free second cruise.
HHV has lots of high-end shops mixed with outlets like the ABC store, sort of a 7-11 on steroids. There are 2 other ABC stores right outside the property. You are also a few footsteps from the heart of Waikiki where shopping and restaurants abound. The Ala Moana Center is just a few blocks in the other direction. We've bought quite a few Hawaiian garments at Sears. Yes, Sears. Suggested by someone at the hotel. There is a Costco on Oahu, but not near HHV. We also had problems finding a suitable grocery store nearby. Fast food in the area is more expensive than outside Waikiki. On drives around the island, we have grabbed breakfast "on the road" paying the normal stateside prices for a large drink and sausage biscuit.
If you are military or DoD civilian, please consider the luau at the Hale Koa, right next door to HHV. It was fabulous.
If you want to stay on the beach, I don't know of a better place than HHV. In fact, unless you are planning to be a hermit, I think HHV is well worth the visit.
Higher floors are better; The Rainbow Tower seems to have the best water views
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.