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

ByHarry

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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.

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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!

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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.

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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!

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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:

  1. 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.
  2. 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.
  3. 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).
  4. 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.
  5. 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.
  6. 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!
  7. Go into Hilton Honors and find the property: Grand Wailea, A Waldorf Astoria Resort.