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Travel To Hawaii For Free Part 2 – Hotel Options

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Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. Links in this post may provide us with a commission.

This past summer we traveled to Hawaii for free!  In part 1 of this series, I talked about how we booked our airfare for free and today I will go into the hotel options.

Anyone who has ever been to Hawaii knows that there are several options of where to visit.  The first place to start when determining hotel options is which island you will stay at.  For the most part, flights are widely available to four islands from the mainland.  Additionally, countless inter-island flights operate daily.  The four main islands to visit are Oahu, Maui, Kauai and the Big Island.

This second part in the series is going to be a short primer on different hotel options in Hawaii and how to earn the points to stay at these properties for free.  This is not an exhaustive list of every property in Hawaii, but instead is a breakdown of the programs and hotels that I feel are the easiest to earn free nights at.  Between the three programs mentioned here, you can stay in a wide range of resorts on all four of the main islands in Hawaii.  Lets get started!

Hyatt Gold Passport:

Hyatt is one of my favorite programs.  To start, the Chase Hyatt Visa awards 2 free nights at any Hyatt upon signing up along with Platinum status which is good for occasional room upgrades and free internet!  It also gives cardholders one free night per year at any category 1-4 Hyatt.  Perhaps the best thing though about Gold Passport is that they a transfer partner of Chase Ultimate Rewards.  This means that points earned from spending and bonuses on cards such as the Ink and Sapphire Preferred can be used for fancy hotel stays!  (I will show you in part 3 how we leveraged this transfer option for our recent trip.)  Now lets take a look at Hyatt’s options in Hawaii.

Hyatt Locations in Hawaii:


Hyatt Place Waikiki Beach – Category 3 – 12,000 points per night

Hyatt Regency Waikiki Beach Resort & Spa – Category 5 – 18,000 points per night.


Hyatt Regency Maui Resort & Spa – Category 6 – 22,000 points per night.

Andaz Maui & Wailea – Category 6 – 22,000 points per night.


Grand Hyatt Kauai Resort & Spa – Category 6 – 22,000 points per night.

Sunset in Maui near the Hyatt Regency.
Sunset in Maui near the Hyatt Regency.

Hilton Hhonors:

The next program worth talking about in regards to redemptions in Hawaii is Hilton Hhonors.  Hilton devalued their award chart quite severely earlier this year, but they have a lot of properties in Hawaii and there are several ways of earning points.  Two credit card issuers have Hilton cards available, American Express and Citi.  The following chart breaks down the options.  Also, the Hhonors Visa Signature is a card that is churnable, meaning you can get the bonus multiple times.  See this Flyertalk thread for more information.

Card Name




Annual Fee

Hhonors American Express


40,000 points

7x at Hilton, 5x Restaurants Supermarkets & Gas, 3x everything.


Hhonors Surpass Card


60,000 points

12x at Hilton, 6x Restaurants, Supermarkets & Gas, 3x everything. Hhonors Gold status.


Hhonors Visa Signature


40,000-50,000 points

6x at Hilton, 3x at Supermarkets, drug stores & gas, 2x everything. Hhonors Silver Status.


Hilton Reserve


2 Weekend Nights

10x at Hilton, 5x airline & car rentals, 3x everything. Gold status. Annual free w/end night with $10,000 in spending during the year.


Hilton Locations in Hawaii: (Note that Hilton has a lot of timeshare Hilton Grand Vacations properties in Hawaii.  The redemption costs for these properties are exorbitant so I am leaving them out.)


DoubleTree by Hilton Alana Waikiki Hotel – Category 6 – 30,000-50,000 points

Hilton Hawaiian Village Beach Resort & Spa – Category 7 – 30,000 – 60,000 points

Embassy Suites Waikiki Beach Walk – Category 8 – 40,000-70,000 points

Hilton Waikiki Beach – Category 6 – 30,000-50,000 points


Grand Wailea, A Waldorf Astoria Resort – Category 10 – 70,000-95,000 points

Hawaii (Big Island):

Hilton Waikoloa Village – Category 7 30,000-60,000 points

There are two caveats to booking with Hilton.  Elites, which would be you if you carry any of the previously mentioned cards, automatically get the fifth night free on award stays.  This is a good benefit and essentially reduces the cost by 20% on longer stays.  Also, cardholders of either of the Hilton American Express cards are eligible for AXON awards.  These are discounted awards for longer stays.  I highly suggest taking a look at this Flyertalk thread which explains all of the redemption options and discounts in great detail!

View from the beach near the Grand Wailea in Maui!
View from the beach near the Grand Wailea in Maui!

Starwood Preferred Guest:

The final program I will tackle in this post is SPG.  SPG is the awards program of many well known brands including Westin, St. Regis and Sheraton.  The best way to earn points for stays at SPG properties is to open the SPG American Express card.  This card comes with 25,000 bonus points and is available in both a personal and business version.  Additionally, SPG points can be transferred to many airline partners at a rate of 20,000 SPG points = 25,000 airline miles.  For this reason, many people consider SPG points to be the most valuable in the award space.  Also, as you will see below, SPG has more properties than either Hilton or Hyatt in Hawaii!

SPG Locations in Hawaii:


Sheraton Waikiki Resort – Category 5 – 12,000-16,000

The Royal Hawaiian, a Luxury Collection Resort Waikiki – Category 6 – 20,000-25,000 points

Sheraton Princess Kaiulani – Category 5 – 12,000-16,000

Moana Surfrider, A Westin Resort & Spa, Waikiki Beach – Category 6 – 20,000-25,000 points


Sheraton Kauai  Resort – Category 5 – 12,000-16,000

The Westin Princeville Ocean Resort Villas – Category 6 – 20,000-25,000 points

The St. Regis Princeville Resort – Category 7 – 30,000-35,000 points


The Westin Maui Resort & Spa Ka’anapali – Category 5 – 12,000-16,000

Sheraton Maui Resort & Spa – Category 5 – 12,000-16,000

The Westin Ka’anapali Ocean Resort Villas – Category 7 – 30,000-35,000 points

Hawaii (The Big Island):

Sheraton Kona Resort & Spa Keauhou Bay – Category 4 – 10,000 points

The great thing about SPG is that you get the 5th night free on all redemptions at hotels in categories 3-7.  This means that a stay in the Sheraton Waikiki Resort could only be 48,000 points for example.  If you were to open both the personal and business versions of the SPG American Express card, that would be enough for a five night vacation on Wakiki!

This could be you!
This could be you!


I hope you can now see that there are quite a few hotel options for Hawaii along with many ways to stay at these beautiful properties for free.  In part 3 I will breakdown exactly where we stayed and how we leveraged many of the cards and transfer options mentioned in this post.  As always, if you have any questions at all please feel free to leave a comment.  This is a lot of information to digest, but it can save you thousands of dollars.  Hopefully when this series is completed, you can begin to form a strategy for a dream trip you are looking to take, whether it is to Hawaii or some other exotic location!

Disclaimer: I DO NOT receive any credit or commission for any of the credit card links in this post.



Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

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Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Shawn Coomer
Shawn Coomer
Shawn Coomer earns and burns millions of miles/points per year circling the globe with his family. An expert at accumulating travel rewards, he founded Miles to Memories to help others achieve their travel goals for pennies on the dollar. Shawn also runs a million dollar reselling business, knows Vegas better than most and loves to spend his time at the 12 Disney parks across the world.

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