Travel Hacking Hawaii: Part 2 – Hotels

This is the second part of my Travel Hacking Hawaii series. See the first part about getting flights to Hawaii here: Travel Hacking Hawaii: Part 1 – Flights

In this post, I’ll review some of the tricks and tips that I know for staying in Hawaii. If you thought the flights to Hawaii were expensive, the hotels are just as expensive if not more expensive. As stated in my previous post, I’ll be looking for ways to stay in Hawaii for a 5 night vacation from August 25-30.


If you’re not one of those people that has to be in a hotel on their vacation, Airbnb and VRBO, are great options. These houses/apartments are listed by their owners as vacation rentals. Doing a quick search on VRBO and Airbnb, I found the following:



As you can see, there are luxury places to stay that accommodate 5-10 people (great for families!) and then there are little apartments or studios. Some of these places are houses/apartments on the owner’s property. Others are completely separate properties or part of an apartment complex. You’ll find that some Airbnbs are lived in by the owner’s when they are not being rented out. Whereas others are simply vacation rentals frequented only by visitors such as yourself.

There is a wide variety of options. In general, this route is probably the cheapest. You obviously won’t get your bed made every day or have a pool to swim in, but the savings can definitely outweigh the hotel amenities. Most of these vacation rentals also have kitchens, which means you’ll be able to cook meals (aka save $$$ by not dining out).

On average, I was able to find vacation rentals for my wife and I for on average $110/night, which works itself out to be $550 for five nights. It is also worth noting that some of these vacation rentals will be more difficult to get to than a hotel. Therefore you’ll have to rent a car to get around. Don’t forget to factor that into your expenses.

Hyatt Hotels

Hyatt has 6 hotels across all the Hawaiian Islands. For my five night stay, I was primarily looking at Oahu and Maui, which has the following hotels:

  • Hyatt Regency Maui Resort (also has a $30/daily resort fee)
    • Cash: $289/night
    • Points: 20k points/night
    • Cash + Points: 10k points + $125/night
  • Andaz Maui at Wailea Resort (+$40/daily resort fee)
    • Cash: $399/night
    • Points: 25k/night
    • No Cash + Points option
  • Hyatt Regency Waikiki Beach Resort and Spa (+$30/daily resort fee)
    • Cash: $289/night
    • Points: 27k/night
    • No Cash + Points option
  • Hyatt Place Waikiki Beach
    • Cash: $256/night
    • Points: 12k/night
    • Points + Cash: 6k + $75/night

There’s also a Grand Hyatt on the island of Kauai. The Grand Hyatt and Andaz hotels are the some of the most luxurious of the Hyatt collection.

Hyatt Place Waikiki Beach

So by just looking at these redemption options the one that stands out to me the most is the Hyatt Place Waikiki Beach. If you stay just on points, you’ll be getting a value of 2.13 cents per point ($256/12,000=$0.0213). If you book on points + cash, you’ll get a value of 3.02 cents per point ({$256-$75}/6000=$0.0302). That is really great value for Hyatt points, which can be earned via the Hyatt Credit Card or transferring Chase Ultimate Rewards. The Hyatt Place may not be quite as nice as some of the resorts, but you also won’t be paying a daily resort fee. I would probably do the points and cash rate, which would cost 30k Hyatt points and $375 for 5 nights.

Another option is to get the Chase Hyatt Credit Card, after spending $1,000 you’ll earn two free nights that can be used at any Hyatt. Better yet, get whoever you’re travelling with to also sign up for the Hyatt credit card. Add those two together that’s four free nights at the Andaz Maui at Wailea Resort (~$1,600) or better yet don’t go to Oahu or Maui and go to the Grand Hyatt on Kauai and use your four free nights there (~$1,850). Still need points to cover the last night? You can transfer 25k Chase UR to Hyatt to redeem for the fifth night.

Grand Hyatt Kauai

Starwood Hotels

I am slightly bias towards Starwood, but that’s because I’ve never had a bad Starwood stay. They always treat me well and the hotels are well maintained. Anyway, Starwood has 11 different hotels across the Hawaiian Islands. Here are the rates for the ones on Maui and Oahu (most of them have resort fees as well):

  • The Westin Maui Resort & Spa
    • Cash: $289/night
    • Points: 20k/night
    • Cash + Points: 10k + $180/night
  • Sheraton Maui Resort & Spa
    • Cash: $287/night
    • Points: 20k/night
  • Moana Surfrider – Waikiki Beach
    • Cash: $304/night
    • Points: 20k/night
    • Cash + Points: 10k + $180/night
  • The Royal Hawaiian, Waikiki
    • Cash: $366/night
    • Points: 20k/night
    • Cash + Points: 10k + $180/night
  • Sheraton Princess Kaiulani
    • Cash: $184/night
    • Points: 12k/night

SPG: The Royal Hawaiian

Overall, in my search for Starwood hotel award redemption options, I was actually disappointed with the lack of value I found in Hawaii. It is worth noting that when you book on points the 5th night is free for Starwood hotels. The Royal Hawaiian might be the best value, but that is going to cost you 80k SPG points for 5 nights. For instance, five nights would cost you $1,830 in cash divided by 80k (20k x 4, fifth night free) equals 2.29 cents per point. Not great value overall considering there are much better uses for SPG points.

Other Hotels

IHG only has 2 hotels in Hawaii. One on Kona and one in Honolulu. Cash rates are: $151 and $180/night, respectively. Points rate are: 30k and 40k/night, respectively. Overall, neither of these are great redemption options unless you’re somehow sitting on a bunch of IHG points.

Hilton has about 10 hotels in Hawaii. There cheapest Hawaiian hotels costs 50k Hilton points or $220/night. Hilton also gives the 5th night free on award stays so your overall cost for a 5 night stay would be 200k Hilton points or $1,100. Hilton points are easy to accumulate. With the AMEX Hilton Surpass card, you can get 6 points/$1 spent at restaurants, grocery stores, and gas stations. This would mean you would need to manufacture spend $33.3k to get 200k Hilton points. All this to say, Hilton probably isn’t the best route to go for Hawaii.

Marriott has 3 hotels in Hawaii. There are two category 7s and one category 8. For a 5 night stay, the category 7s cost 140k points and the category 8 costs 160k points. On average, you’re looking at value of around 0.75 cents per point. This is about average for Marriott award redemptions. The Chase Marriott credit card has a sign up bonus of 80k points after spending $3,000 in the first three months. However, after the sign up bonus, accumulating Marriott points is not easy. While Chase UR do transfer to Marriott, there are a handful of travel partners that offer much better redemption value. Therefore, I probably wouldn’t transfer UR to Marriott.

Closing Thoughts

Looking at award redemption options, I was actually kind of disappointed. Overall, I didn’t feel like there were any amazing award options. Using the two free Hyatt nights (via the Chase Hyatt credit card) probably gives you the most bang for your buck. With that being said, I personally would probably choose to stay at a vacation rental through Airbnb or pay cash to stay at the Sheraton Princess Kaiulani.