How to Stay at a Luxury Resort in Maui, Hawaii: Top 2 Most Affordable Methods (Hilton Honors)

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MAY 2025 UPDATE: Please note that Hilton Honors recently had a devaluation of their points, meaning that it will now cost more Hilton points to redeem certain properties that were listed below prior to this update. Also, the targeted offer to buy Hilton Honors points has updated, so you may have a different maximum amount of points that you will be able to buy per calendar year. These methods will still work today, although it will likely be slightly more expensive to book these same properties due to the devaluation update, and you may have to pool points with a travel partner to obtain the required amount of points due to the new cap of buying Hilton points. Additionally, keep in mind that American Express Hilton Honors sign-up bonuses change frequently, so your bonus may vary depending on the targeted offer.

How You Can Stay at One of the Best 5 Star Resorts in Maui, Hawaii Using Hilton Honors!

Is staying at one of the top resorts in Maui, Hawaii sound like a dream to you? Maybe you have watched movies or tv shows such as White Lotus or Just Go With It and wished you could stay at a similar resort. We will break down the exact strategies of how we were able to spend our honeymoon at a luxury 5-star resort in Maui, Hawaii in the Wailea Beach area for a significant discount! We will also show you much cheaper strategies of how you can do the same for yourself! Using Hilton Honors rewards and points is one of the best ways you can utilize to book that dream honeymoon, anniversary stay, couples vacation, family vacation, or even as a solo traveler! We personally used this strategy to stay in the Wailea Beach area for our elopement wedding!

Option #1: Using Hilton Honors Credit Card Sign-On Bonuses for Rewards Nights and Points

Overview

The first method is to earn sign-up bonuses through the Hilton Honors credit cards issued by American Express! There are 3 total credit cards (as well as 1 business credit card) that you are able to apply and earn all 3 bonuses if you do it properly. Pair this with a partner, and you will have even more points to use for a longer stay! We will go into the method of how to accumulate a ton of Hilton Honors points through Amex welcome bonuses.

The resort that we will be looking to redeem at the end of the method is a property in Maui, Hawaii called Grand Wailea, a Waldorf Astoria Resort. This is a beautiful resort located in the Wailea Beach area. We had a wonderful experience at this property. They upgraded our room view, complimentary, and even decorated the room for us during our wedding day!

Method

The personal Hilton Honors credit cards and business credit card are listed below:

Hilton Honors Co-Branded Credit Cards (American Express)

Here would be the proper steps for this method to maximize your point accumulation:

First, you should apply for the lowest tier card (Hilton Honors credit card) and hit the minimum spend ($2,000 in the first 6 months) to get 80,000 Hilton Honors points.
After you hit the bonus on the Hilton Honors, you will want to move to the Hilton Surpass credit card, which is the mid-tier card and hit the minimum spend ($3,000 in 6 months) for the Surpass to earn another 130,000 points.
Finally, you will want to apply for the highest tier card (Hilton Aspire) and hit its minimum spend ($6,000 in 6 months) to earn 150,000 points. Be sure to hit the Surpass minimum spend first before applying for the last card (unless you are able to hit both spends quickly).
At the end of the minimum spends, you will have a total of 393,000 points, which includes 360,000 from bonuses + at least 33,000 from x3 points on all spend on Hilton Honors credit cards.
At this point you have a couple options to earn the remaining points required (440,000 points needed for a 5 night stay!):
- You can have your partner or fellow traveler earn one or more of these bonuses to accumulate at least an additional 86,000 points (80,000 points from the bonus and 6,000 from x3 spend from the lowest tier Hilton Honors card).
- You can simply purchase the remaining Hilton Honors points that you need to get to 440,000 points (you will need to purchase at least 47,000 points to get to this amount from 393,000 points). Go into your Hilton Honors account and navigate to the option to purchase points, or you can simply click here.
Once you finally have 440,000 points, you will be able to book your stay for 110,000 points per night! It gets even better because you will have at least Silver status with Hilton by holding one of their co-branded credit cards. This will give you the “fifth night free” benefit, meaning that by booking 4 nights with points, you will get an additional free night, completely for free! This means you will have a total of 5 free nights!
Go into Hilton Honors and find the property: Grand Wailea, A Waldorf Astoria Resort.

Here you can see on the calendar for June 2025, as an example, that there is a ton of availability for a standard room of 5 nights in a row! Select one of the dates in any month, costing 110,000 points per night, that will work for your own travel schedule:

From here you will want to choose a standard room, either a Terrace View – 1 King Bed or Terrace View – 2 Queen Beds.

Finally, you will be able to book your stay for only 440,000 points! Your free night will automatically be applied. Additionally, the wonderful thing about redeeming rewards nights is that the $55.00 USD resort charge per night is completely waived! If you happen to get the Hilton Aspire card, you can actually redeem an additional night (free standard reward night benefit) on top of your 5 night stay, making it a 6 night stay!

Total Cost

The total cost to implement the credit card welcome bonus method is estimated with the following fees you should expect:

No annual fee from the Hilton Honors Credit Card.
$150 annual fee from the Hilton Honors Surpass Credit Card.
$550 annual fee from the Hilton Honors Aspire Credit Card.
Any additional points purchases (costing 0.5 cent per point if you purchase at least 5,000 points). You will likely need to purchase up to 48,000 points, costing $240, depending on what option you used in step 5. We will break down Hilton Honors point purchases in more detail when we discuss the next method.
Any other additional annual fees if you have a partner or fellow traveler apply for additional Hilton Honors credit cards to earn the welcome bonuses. You will not need to purchase any additional Hilton Honors points if you used this method. Instead, you will simply pool points to reach the 440,000 points required.

When we add up all of the fees that you will be required to pay, the total will come out to less than $1,000 on the higher end. If we compare this to what you would be required to pay when booking the same property on the same dates and same room type with cash, you can see that the total cost of this would be a whooping $5,393.16! You will effectively get over an 80% discount if you were to use this first method!

It would cost **$5,393.16** to book 5 nights at this property of the same room type using money!

These are some disclaimers to note when talking about credit cards:

NEVER carry a balance on any credit card! We do not (and never will) advise you to go into credit card debt for this strategy!
Keep in mind your financial situation when going for a card member bonus. Please only spend on purchases that you would have otherwise made already! We would recommend saving this strategy for an already planned big future purchase that you are able to put on a credit card (wedding costs, tuition, furniture, etc.).
Always follow the terms and conditions of American Express. Keep your cards open for at least one year before making any decision to cancel. Attempting to “game” the system will blacklist you from American Express.
Keep in mind of American Express “pop-up jail” (American Express may inform you that you will not qualify for another sign-up bonus when applying past your first Amex credit card). This is Amex’s way of suppressing the amount of rewards offered to you, and usually time will resolve it. You may have to adjust this strategy for the longer-term if you run into this issue.

FAQ Section

How to Combine Hilton Points Between Two Accounts?: You will need to pool points between you and your travel partner to stack the total amount of points to use the fifth night free benefit! Pooling points is completely free, and for this reason, we don’t reccomend “gifting points” as previously recommended due to the change of having a fee now associated with gifting points.
How to Earn “Fifth Night Free” Benefit?: The fifth night free benefit is available to Hilton Honors Silver, Gold, or Platinum status. The Hilton Honors American Express card will give you automatic Silver status while the Hilton Honors Surpass American Express card will give you automatic Gold status! Additional ways of earning the required Hilton Honors status is through:
- Holding the American Express Platinum card (complimentary Gold status)
- Having T-Mobile Magenta status (complimentary Silver status)
- Requesting a status match with Hilton Honors (for Gold status) if you have a similar status tier with another loyalty program (good for 90 days).
Why is the Point Redemption Much More Expensive?: This method will only work with standard rewards nights. If you see dates costing more than the specified point redemption amount, this means that a standard rewards night is not available at the property on the specified date. Having four people on the reservation will probably be much more difficult to find standard rates versus only having two people on the reservation.
Unable to Purchase Hilton Points?: You will be able to purchase Hilton points after 90 days of opening a Hilton Honors account (free to sign up) or 30 days with qualifying account activity (booking hotel stays, earning Hilton Honors points, or redeeming Hilton Honors points)
Do Hilton Points Expire?: Hilton Honors points do expire after 24 months of inactivity (be sure to either reserve nights, earn points through Hilton spend or Hilton Honors credit card spend, or redeem your points to keep your points from expiring)
Do Hilton Free Night Certificates Expire?: Hilton reward night certificates will only be good for one year. You may have the option to extend the rewards night for up to two weeks past the expiration date via customer service chat. Additional extensions may be granted if you directly call customer service, but these are not the standard. Keep this in mind when having to hit your minimum spend for the credit card sign-on bonuses because you will need to take account of time with the expiration dates of your rewards nights.
How to Redeem Hilton Free Night Certificates?: You will need to call Hilton Customer service to redeem your rewards nights, and they will be able to merge any separate reservations that you booked with points.
Why Do I Have a Different Amex Hilton Honors Welcome Bonus?: American Express welcome bonuses are also usually targeted, so your welcome bonus offers may be different. It may take some time to be able to implement this strategy. If you are lucky, sometimes cards will include a free night certificate in addition to the large point bonus that you receive after hitting the minimum spend!
Why Don’t I Qualify For a Second Hilton Honors Welcome Bonus?: To qualify for an additional sign-on bonus, be sure to apply for the lowest tier Hilton card first, then apply for the mid-tier (Surpass) second, and finally the high-tier (Aspire) last. American Express has a family card sign-up bonus restriction, meaning that if you have received a higher sign-on bonus from one of the cards in that “family” (Hilton Honors co-branded credit cards) you no longer qualify for a sign-on bonus from a lower-tier card. Additionally, see the disclaimers above regarding Amex “pop-up jail”.