Hawaii - Ideas for points to get hotel costs down

I am helping a coworker plan a trip for him and his wife to Hawaii. He has been watching me go on trips using miles and points and wants my help planning his trip. The only thing is I don't have much experience with hotels in Hawaii as I have always had family to stay with when I went! :)

I have a good plan for him for flying, but the hotels have me a bit stumped.

He would like to keep cost down by using points to stay at hotels if possible. I would like to suggest a card for him and his wife to both sign up for (both have excellent credit). He has 40K Hilton points currently but that is about it. I think the best value for him might be getting the SPG Amex and using a cash/points option. What do you think?

He hasn't decided which island yet (I know, makes it a bit harder) but for sure knows no Oahu. He was there for 6 months once and would like to try elsewhere.

It's not points-related, but the Daily Getaways promotion still has available its Diamond Resorts offer for 5 nights ($540 w/ AMEX). They have locations in Kauai (The Point at Poipu) and Maui (Ka'anapali Beach Club). I don't have experience with either property, but for $108/night in Hawaii they may be worth considering.

The 70k Marriott card may also provide some decent options. I believe there is even a Cat 4 somewhere in the islands (Kauai?) that could serve as their 1st night hotel to take advantage of the 1-4 free night that comes with the card.

SPG probably provides the most versatility, but their points are probably the most difficult to acquire too.

For the Oahu portion, I would seriously consider using Hotwire or similar. It's what I do every time there. You are almost always going to find a Waikiki 4 star for the mid-150s. I've been at Prince, Hyatt, Sheraton, etc. If he's concerned about nonrefundable, he could even wait to the last minute. With this kind of option available, I really don't find it a good value to waste points on Waikiki. The points required will likely be inflated relative to the cost of paying. Using them for an outer island will almost always yield a better return.

Edit: oops, misread 'no Oahu'..

Now, my real reply..

Maybe he should consider a Hyatt or (upcoming) Fairmont card for both him and his wife, resulting in 4 free nights.

Hyatt Poipu, Hyatt Ka'anapali, Fairmont Kea Lani, Fairmont Orchid, all very nice choices.

SPG Amex is a good idea for him and his wife. They don't always offer the Cash and Points options, but both the Westin Maui and Sheraton are 12,000 points per night. Don't know what the latest CC sing up bonus is but should be able to get at least few nights this way.

Both of them should apply for the SPG Amex (one should get it first and refer the other for an extra 5k points ;)); you can transfer from one account to the other for free. Book the Westin Maui for four nights at 12k each and get the fifth night free - great value to get 5 nights with just two card applications!

Each can also apply for the Chase Hyatt, which could be used for four free nights at the Grand Hyatt in Kauai.

Love it! Thank you! You all suggested a couple of ideas I hadn't thought of. He will be super happy.

get the most bang for your buck in the marriot 70k offer....then use it in kona...they have a cat 4(only one til a courtyard in maui opens up)...then use the rest of the points at waikaloa marriort or otherwise...

probably the best deal would be to get the hyatt card..then go stay at the grand hyatt kauai