I had my first two trips to Hawaii this year, and have stayed in both places twice (recently). In January, I went to the Big Island and Oahu for work. I stayed at Waikoloa Village 3 nights, and the Grand Naniloa Doubletree in Hilo for one night, then flew to Honolulu and stayed at the Hilton Garden Inn Waikiki for 4 nights and Hilton Hawaiian Village for 3 nights. In May I had to go back. This time I stayed at HHV for 3 nights, a Courtyard on Maui for 2 nights, and then 7 nights at HWV.

Here are my thoughts on the places that I stayed -

• HWV: This is a *very* large property. Both of my stays were in the Ocean Tower. Both times I was upgraded from a "resort view" to "partial ocean view". There are a couple of options for getting around. There's a monorail-looking train/tram thing that runs end to end through the resort on some sort of schedule (every 10 minutes or so?). It takes 10-15 minutes to ride the full distance, as it stops 5 or 6 times and waits a minute or two for loading/unloading. On the plus side, it's air conditioned. There are also boats which will take you on a parallel route through canals. This is quite a bit slower, probably on the order of 30 minutes end to end. I was never able to figure out the schedule. The number of boats running at any one time seemed to vary quite a bit, so I only took the time to wait for it twice. The last choice is that you can walk. There are paths throughout the property, and "hoofing it" is the only way to get to the attractions on the ocean side of the lagoon (Lagoon Grill, Dolphin Quest Village, Ice Cream Stand). I tend to walk without dawdling, and it took me around 7-10 minutes to walk from the lobby to the Ocean Tower. There are (to my mind) surprisingly few dining options on site, and they are expensive and close early. My wife and I had dinner at Kamelua Provision Company. 1 Surf and Turf, 1 Filet and 2 glasses of wine pushed $150 with the tip. There are two asian restaurants, one is closed for remodeling, the other is closed. The Mexican cantina in the Ocean tower isn't bad, nor is the Lagoon Grill. We weren't impressed with the food at the Italian place, though we did enjoy sitting on the patio, watching a barracuda watch us eat from the canal. There are a couple more options in the nearby shopping centers, but beyond that you will start to notice how remote this place is - 30 minute drive into Kona. Valet parking fee recently increased from $30/day to $37/day. All that said, I liked it, and will probably stay here again.
• Hilo Doubletree: I wasn't impressed with this one. The lobby is breathtaking. Parking was inconvenient (though free). The restaurant was weird when I was there in January, but maybe they have fixed it? At the time, the cost was $25 and it was sort of a mini-buffet, but without choices. You grabbed a plate, spooned on your entree and sides, and they brought water/soda/coffee. There was a plate of the type of desserts that you tend to see at hotel conferences - tiny cheesecakes, etc. My room seemed old. it was really kind of disconcerting after seeing the lobby. AC didn't work, so it was uncomfortably warm.
• HGI Waikiki: This could be any hotel anywhere (at least anywhere near saltwater). Nothing wrong with the place, I just felt like I could have been in Ft Lauderdale, or Huntington Beach. Nothing very "Hawaii" about it. If you are driving a car, the valet parking entrance can be a challenge to get to. As you come down Kuhio Ave, the hotel is on your left, but the entrance is on a one way street coming toward you. You have to go around the block to get to it, and if you miss one of the turns it's "one way hell" trying to get back to where you want to be. It's about a 5 block walk to a very nice beach, so there's that.
• HHV: As everyone above has said, this place is a madhouse. My first trip, we stayed in the Ali'i Tower and it was totally worth the extra points. That tower has its own separate check in area, a private pool with hot tub, and gives you a bracelet that you can use to jump the line at just about any restaurant on property. As a diamond, I was upgraded from a "resort view" room to a "partial ocean view" room at no charge. The upgraded room had a balcony that looked out over the main pool and wrapped around the end of the building to face the ocean. Second trip I was in the Tapa Tower. I had to use the main checkin area, but there is a desk for Honors members where the line was nonexistent when I checked in/out. Valet parking was $30/day. There are tons of shops and restaurants in and around this property, so plenty of opportunity for you to buy a bunch of crap that you can get cheaper at home, if that's your thing.

So the summary is that I liked both, but for different reasons. If I had to pick a winner it would be HWV, hands down. I loved the seclusion and the more laid back feeling on the Big Island. I can be in a city anywhere....