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I Booked a $4,200 Luxury Vacation at Hawaii’s Grand Wailea Resort for FREE Using Hilton Honors Points (So Can You!)

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I Booked a $4,200 Luxury Vacation at Hawaii’s Grand Wailea Resort for FREE Using Hilton Honors Points (So Can You!)

Jasmin BaronI Booked a $4,200 Luxury Vacation at Hawaii’s Grand Wailea Resort for FREE Using Hilton Honors Points (So Can You!)Million Mile Secrets Team

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INSIDER SECRET:   Using Hilton Honors points for a bucket-list resort stay is already amazing.  The icing on the cake is having the Hilton Honors Aspire Card from American Express for its resort credit and Diamond elite status.

Collecting Hilton Honors points is a key strategy for getting free hotel stays among travel enthusiasts.  The best use of Hilton points totally depends on your travel style, whether you enjoy fancy resorts or prefer stretching your points at more moderate hotels.

I’m usually in the latter camp, but recently made a big splurge and booked 5 nights at the ultra-luxurious Grand Wailea – A Waldorf Astoria Resort in Maui for my family’s upcoming Hawaii vacation.  Using Hilton points I’ve earned from the Hilton Honors Aspire Card from American Express and other Hilton cards, plus benefits like the $250 Hilton Aspire resort credit and having Hilton status that gets us the 5th night free on award bookings, we’re getting a stay worth ~$4,200 – for free.  

That’s not something I’d normally be able to pay cash for, but here’s where miles and points truly shine – by making memories and having experiences you might not otherwise be able to afford.  The kids are absolutely ecstatic about the resort’s multiple pools and waterslides (“It has a water elevator, Mom!”), lazy river, and incredible beach, and they’re at the perfect age to enjoy it.  Sure, it cost a chunk of Hilton points, but … if not now, when?

Even if you’re brand new to the miles and points hobby, you can easily plan a similar trip when you earn Hilton Honors points with travel credit cards.  I’ll take you step by step through the process.

With Hilton Honors Points and Perks From the Hilton Aspire Card, My Family Will Soon Enjoy a Stay Worth ~$4,200 at the Luxury Waldorf Astoria Grand Wailea for Free

You Can Use Hilton Honors Points to Book the Grand Wailea in Hawaii (Or Any Epic Hilton Hotel)

I’ll use my experience booking the Waldorf Astoria Grand Wailea as an example, but you can apply most of the same principles to just about any other Hilton hotel award stay.

Step 1.   Earn Hilton Honors Points (I Did It With Welcome Bonuses and Spending on Hilton Credit Cards)

If you’re already collecting Hilton points, great!  But if you’re starting from scratch, you’ll want to begin by setting up a Hilton account (free to join and only takes a couple of minutes).

Once you’ve done that, it’s time to start earning Hilton points (scroll down to the next step if you’re unsure of how many you’ll need).  There are 4 AMEX Hilton cards (3 personal, 1 business) that earn Hilton points directly, and all of them currently have higher than normal welcome bonuses.  This makes it a good time to apply because AMEX only lets you earn the intro bonus on a particular card once, per person, per lifetime:

Card Name Welcome Bonus & Minimum Spending RequirementsOur Review
Hilton Honors Aspire Card from American Express

150,000 Hilton points after spending $4,000 on purchases within the first 3 months of opening your account. Terms Apply.Read our Hilton Aspire review
Hilton Honors American Express Ascend Card

125,000 Hilton points after spending $2,000 on purchases within the first 3 months of opening your account. Terms Apply.Read our Hilton Honors Ascend Card review
Hilton Honors American Express Card
75,000 Hilton points after spending $1,000 on purchases within the first 3 months of opening your account. Terms Apply.
Read our Hilton Honors Card review
The Hilton Honors American Express Business Card125,000 Hilton points after spending $3,000 on purchases within the first 3 months of opening your account. Terms Apply.Read our Hilton Business Credit Card review

My favorite of the bunch is the AMEX Hilton Aspire, which is in my wallet right now (but I’ve had a couple of the other cards too).  The Hilton Aspire benefits and perks include:

  • A weekend night award (at participating Hilton hotels) when you open your card, then every year on your account anniversary
  • Automatic Diamond Elite status (100% bonus points on paid stays, upgrades to a suite when available, executive hotel lounge access, etc.)
  • Priority Pass Select airport lounge access (bring 2 guests for free)
  • Up to $250 annual airline fee credit
  • Up to $250 annual Hilton resort credit at participating resorts
  • Up to $100 property credit at Conrad and Waldorf Astoria hotels per stay of 2+ nights
  • Terms Apply

While the $450 Hilton Aspire annual fee (See Rates & Fees) might seem like an insane amount of money to spend on a credit card, I promise it is well worth it if you like Hilton hotels (as you’ll see later)!

There are other ways to earn Hilton points indirectly with credit cards.  For example, Hilton is an AMEX transfer partner, so if you have one of the cards below, you can transfer your AMEX Membership Rewards points to Hilton at a 1:2 ratio:

Card Welcome Bonus & Minimum Spending Requirements
The Business Platinum® Card from American Express

Up to 75,000 Amex Membership Rewards points

50,000 Membership Rewards points after spending $10,000 on purchases in the first 3 months of opening your account, plus earn an extra 25,000 Amex Membership Rewards points after spending an additional $10,000 on qualifying purchases within the first 3 months of opening your account. Terms Apply.
The Blue Business℠ Plus Credit Card from American ExpressNo welcome bonus
The Platinum Card® from American Express

60,000 Amex Membership Rewards points after spending $5,000 on purchases within the first 3 months of opening your account. Terms Apply.
American Express® Gold Card35,000 Amex Membership Rewards points after spending $2,000 on purchases within the first 3 months of opening your account. Terms Apply.
American Express® Business Gold Card
35,000 Amex Membership Rewards points after spending $5,000 on purchases within the first 3 months of opening your account. Terms Apply.
Business Green Rewards Card from American Express5,000 Amex Membership Rewards points after your first purchase on the card within the first year of card membership. Terms Apply.
Amex EveryDay® Preferred Credit Card from American Express
Card Image Not Available
15,000 Amex Membership Rewards points after spending $1,000 on purchases within the first 3 months of opening your account. Terms Apply.
Amex EveryDay® Credit Card from American ExpressCard Image Not Available
10,000 Amex Membership Rewards points after spending $1,000 on purchases within the first 3 months of opening your account. Terms Apply.
The information for the Amex EveryDay Preferred Credit Card and Amex EveryDay Credit Card has been collected independently by Million Mile Secrets. The card details on this page have not been reviewed or provided by the card issuer.

Transferring to Hilton is not the best way to use AMEX points, because you’ll typically get more value with other partners.  However, if you’re a few points short for an award stay, it’s a good way to boost your balance.  You can also check out our post on how to earn Hilton Honors points for other ways to top off your account.

Step 2.   Find and Book Your Award (and Get Your Bag of Tricks Ready!)

Search for Available Award Nights

Once you’ve got a nice stash of Hilton points and are ready to travel, it’s time to search for an award.  Read our full guide on how to use Hilton Honors points for step-by-step instructions if you’re new to the process (it’s not terribly different from searching for a paid hotel stay).

Knowing how many points you’ll need is a bit tricky because the Hilton award chart no longer exists.  Instead, you’ll have to search for hotels and dates you’re interested in to check out the award price, or use the Hilton Points Explorer tool to see the minimum and maximum number of points you’ll pay for a standard room at a particular hotel.

Top-tier Hilton resorts like the Grand Wailea charge 95,000 Hilton points per night for a standard room, but most Hilton locations cost less than that.  The least you’ll pay is 5,000 Hilton points per night, but there are very few hotels at that level.

Booking award nights can be a bit of a challenge if you’re traveling as a family.  Standard award rooms are typically suited to a maximum of 4 guests (and overseas, just 1 or 2 people) so you might have to jump through a few hoops to find the room you need.  When I started my award search at the Grand Wailea for our party of 5 (3 kids, boyfriend, and self), there were no standard award rooms available – although they were happy to offer me a premium room award (suite) for a whopping 604,000 Hilton points per night.

Nope!  Hilton Did Kindly Remind Me a Party of 5 Would Exceed the Maximum Occupancy Limit for Many Hotels

Here’s where a few hotel award booking tricks came in handy.  I got rid of one of the kids from the booking (don’t worry, they’re still coming!) and searched for 2 adults and 2 children instead.  Voila!  Standard rooms appeared at 95,000 Hilton points per night.

If You Can’t Find the Award Room You Want, Try Reducing the Number of Guests to See What You Find

Here was another stumbling block – despite the fact an award became available for 4 people, the standard award room at the Grand Wailea is a “Terrace View King” with one king bed.  While my kids are little enough to pile into bed together, the 5 of us certainly weren’t going to be crammed into a single king bed.

A Room With One King for 4 People? Not Sure That’s Gonna Work

There’s a sofa in the picture.  Frustratingly, the room description made no indication if it was actually a pull-out couch.  And (unlike some other hotels) there was no mention of maximum guests per room.

No Mention of a Pull-Out Couch … Hmm

So I picked up the phone and gave the Grand Wailea a call directly – first, to find out if that was a sleeper sofa, and second, to ask if it would be a problem having 3 kids in tow instead of two.  The agent assured me that it was indeed a sofa bed, and that it was no problem at all to have 3 kids in the room – the rooms are super spacious and lots of families have no trouble making a one king room work for them.  She also made a request on the file for a Diamond upgrade because we were a larger family.

Big caveat here:  Not all hotels are so flexible (especially outside of North America).  Some set a very firm limit as to the number of guests allowed and enforce it strictly, so be sure to do your research if you’ve got a larger group.

Book Your Room and Take Advantage of Your 5th Night Free (With Elite Status)

Having any level of Hilton status allows you to get the 5th night free on award stays of 5+ nights.  All of the AMEX Hilton cards come with automatic elite status (Diamond with the AMEX Hilton Aspire, Gold with the AMEX Hilton Ascend and AMEX Hilton Business, and Silver with the AMEX Hilton Honors), so having one of these cards is a terrific way to make your Hilton points go further.

I’ve got Diamond status from the Hilton Aspire, so instead of paying 475,000 Hilton points for a 5-night stay at the Grand Wailea (95,000 points X 5 nights), I only spent 380,000 Hilton points (95,000 points X 4 nights + 5th night free).  Here’s what the booking looks like:

Getting the 5th Night Free With the Hilton Status From My Aspire Card Meant I Saved 95,000 Points

This same idea works whether you’re booking an inexpensive Hampton Inn or fancypants Conrad hotel.  A few rules to keep in mind:

  • Only standard room (not premium room) award bookings are eligible
  • Paid stays and Points and Money bookings don’t qualify either
  • You can’t combine a weekend night certificate with points and still get the 5th night free (trust me, I tried – I’ll save my Aspire weekend night for another time)

The final tally?  For 380,000 Hilton points we’re getting 5 nights (average 76,000 points per night) which, if paid with cash, would have cost nearly $4,200.

Room Rates at the Grand Wailea Are Over $800 a Night With Tax (and Sometimes Even More) – I’ve Never Paid That Kind of Money for a Hotel Room

If you like to keep track of such things (I prefer not to focus on points value but some do!), we’re looking at ~1.1 cents per Hilton point, which is much higher than the average Hilton points value of 0.5 cents per point.  I’m not complaining. 🙂

You might have noticed a couple of items in the screenshot above.  The Grand Wailea charges a mandatory resort fee of $40 per night, which is included in the final cash cost.  However, Hilton does not add resort fees to award stays booked with points or weekend night certificates (however you will pay resort fees for Points and Money bookings).  So we won’t have to worry about that additional cost.

Where we will have to pay extra is for valet parking at $35 per night because we’re renting a car.  But we won’t pay anything out of pocket because having the Hilton Aspire makes this stay truly free.

Step 3.   Make the Most of Your Hilton Credit Card Perks

The Hilton Aspire Is Saving Us $250

This is why I recommend the AMEX Hilton Aspire if you’re planning a similar vacation.

Hilton Aspire cardholders get a $250 Hilton Aspire resort credit every account anniversary year.  It’s valid for room rate and room charges at eligible Hilton resorts, which includes hotel restaurants, spa treatments, and parking.  I’ll use my Aspire card to pay for room incidentals, which will cover the entire valet parking cost (with a few bucks left over for some mai tais and snacks by the pool).

The Diamond status that comes with the Aspire also gets you complimentary breakfast at Hilton hotels, executive lounge access at hotels that have one (free food, drinks), and upgrades up to a 1-bedroom suite if available.  Unfortunately, the Grand Wailea is a bit of an exception in that:

  • The “free” breakfast is actually a $30 credit at the hotel’s breakfast buffet restaurant, which is crazy expensive
  • Executive lounge access is reserved for guests in the exclusive Napua Tower, and,
  • Reports online suggest it’s rare to get an upgrade to the Napua Tower, even as a top-tier Diamond elite

So I’m not counting on using these perks for our stay.  But if you’re staying at most other Hilton hotels or resorts, it should be a no-brainer to get a free breakfast, lounge access (where available), and a better room.  Even Hilton Gold status (which comes with the AMEX Hilton Ascend and AMEX Hilton Business) entitles you to free breakfast at Hilton hotels.  Before I had the Aspire, the kids and I enjoyed a wonderful free breakfast at the Conrad Tokyo from having Hilton Gold status that would have cost $140, so it can be totally worth keeping one of those cards even if you only stay at Hilton a couple of times a year.

I’m Not Counting on Free Breakfast on This Trip, but My Family’s Sure Enjoyed It at Other Hilton Hotels

Earn Extra Discounts With AMEX Offers (Stacks With Aspire Resort Credit)

That’s not the only AMEX card perk to consider.  With any AMEX card, you’ll get access to AMEX Offers, which are targeted discounts you’ll get when you add an offer to your card and make a qualifying purchase.  This includes retail merchants, restaurants, services, hotels, and other travel.

You’ll often see offers for Hilton hotels (or specific brands) included in the deals, and right now is no exception.  On my Hilton Aspire card, I’ve got 2 that apply to our stay (I’m seriously thrilled):

So in the first case, if I spend $500 on my Hilton Aspire on room incidentals like valet parking, hotel restaurant meals, or activity fees, I’ll get $100 back from the AMEX Offer, plus another $250 back from the Hilton Aspire resort credit (you can stack both credits).  Net out of pocket cost for $500 worth of stuff would be $150 ($500 spent – $350 in credits).

In the second case, if we spent $1,000 on room charges (probably pretty easy to do at the Grand Wailea), I’d get $200 back from the AMEX Offer and $250 back from the Aspire resort credit.  In that case, the net cost would be $550 ($1,000 spent – $450 in credits).  Maybe we will book that luau after all!

Now if both the AMEX Offers above stack, that’d be – as the kids would say – totally lit.  (We’re taking bets on it at MMS;  I promise to report back).

Bottom Line

You don’t have to be wealthy to enjoy an incredible luxury resort vacation at a Hilton hotel like the Waldorf Astoria Grand Wailea in Maui, Hawaii.  My family is using Hilton Honors points to stay 5 nights in June, and getting a vacation worth almost $4,200 for free.

You can use the same strategies to do the same thing at just about any Hilton hotel, including:

I’d love to hear about how you’ve used your Hilton Honors points for incredible vacations (especially if you’ve stayed at the Grand Wailea).  Please share in the comments!

Curious now about Hilton points and the Hilton Honors loyalty program?  Here are a bunch of guides to check out:

And while you’re here, please subscribe to the Million Mile Secrets daily email newsletter for more tips, tricks, and insights into traveling for free.

For rates and fees of the Hilton Aspire Card, please click here

Hilton Honors Aspire Card from American Express

Hilton Honors Aspire Card from American Express

  • Earn 150,000 Hilton Honors Bonus Points with the Hilton Honors Aspire Card from American Express after you use your new Card to make $4,000 in eligible purchases within the first 3 months of Card Membership. Plus, enjoy a free Weekend Night Reward within your first year and every year after renewal.
  • Earn 14X Hilton Bonus Points when you make eligible purchases on your Card at participating hotels or resorts within the Hilton Portfolio.
  • Earn 7X Bonus Points for eligible purchases: on flights booked directly with airlines or, on car rentals booked directly from select car rental companies & at U.S. restaurants.
  • Earn 3X Hilton Honors Bonus Points for all other eligible purchases on your Card.
  • Enjoy up to $250 in Hilton Resort Credits on your Card each anniversary year, when you stay at participating resorts within the Hilton portfolio.
  • Enjoy complimentary Diamond status with your Hilton Honors Aspire Card.
  • $450 annual fee.
  • Terms Apply.
  • See Rates & Fees
Terms Apply | Rates & Fees

More Info

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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I just booked 5 nights in Washington DC and used free weekend night certificates both before and after for a total of three free nights with the fifth night free benefit, no problem. They can link the reservations to keep the same room.


Hi Brian – Thanks for sharing! Yes, you can tack the weekend night to the beginning or end of a 5-night points booking – so long as it’s an actual weekend night. It wouldn’t work for the dates we needed to stay because our 5 nights overlaps the weekend.

Just a heads up, we stayed at the Grand Wailea a month ago and the $30 credit has been changed to a ‘continental breakfast plate’ at the main restaurant. The plate includes fruit, muffin , croissant, and a very small parfait. Apparently this policy was just put into place. The out of pocket price for this would be $20 if you had to pay. The $30 credit was definitely a better deal.


Hi Julie – Great info, thanks! Was it a continental breakfast plate for each person in the room or just a maximum of 2?

Can’t wait to hear the trip report and see if you are upgraded or not. The Grand Wailea is a beautiful resort. Definitely on my bucket list!


Hi Sara – I’ll definitely report back!

I stayed at Grand Wailea first two days of December, six adults, two children in two rooms. Both husband and myself have the Aspire card and at the time AMEX offered $70 on $300 spend. At that time, the diamond breakfast benefit was $30 per room and could be used anywhere on property at any time during the day, just charge to your room and $30 a day credit posts on the statement. Cafe Kula sells a pretty good pizza, great for kids. Anyway, I asked for price to upgrade to Napua Club and was charged $150 per day per room, sounds high but full breakfast for 8, afternoon was just snacks, evening was not a full meal but could be for the kids, and chocolate time was well worth it, not to mention the bar avail from 4-9pm esp when mai tais etc sell for $18 at Grand Wailea. So even tho it was $600 for the lounge, we had the $500 resort credit from Aspire, and $70 AMEX credit when charging $300 to the room. Oh, we took the pizza up to the lounge and had our cocktails at the same time. The Napua Club rooms are facing the front of the resort, ocean view – well worth the up charge for us. If you are up before the breakfast is served, they have coffee, juice, and fruit on a table by the door. We each used one free night cert and 95,000 points. And on a side note, the Napua Club gave my grand children a Grand Wailea stuffed animal, I believe the choice was a whale or a turtle. You also can get your pool wristbands, sunscreen, and check out at the club, saves much time. The 2 queen bed rooms do not have a sofa so you may want to stick to the King bed with pull out sofa. If you have a later flight, after you checkout, the Club will give you gate keys so you can use the amenities till closing, and Grand Wailea has a hospitality room to shower and change. It was great fun, can’t wait to go back and will most definitely upgrade to the Napua Club.


Hi Debbie – Thank you SO much for sharing – it sounds like you had an incredible trip – and I love the angle of using the Aspire credits and AMEX Offer for the upgrade fee.

Will seriously consider paying for an upgrade now (still crossing fingers we’ll get one from Diamond, but who knows) if it’s the same price given everything you’ve suggested – I imagine it’s easy to blow through $150 a day between breakfast, drinks, snacks, and light meal for a group.

Did you find it was hard to keep track of the kids given the size of the resort?

We went during slow period and had no issues with keeping track of the kids, (si adults)even tho the first night was sold out we didn’t notice a hectic hotel at all. Also wanted to share, we bought body boards at Costco and gave them away to kids before leaving, many families do that, inflatables, body boards, sand toys.


Hi Debbie – Great (and thank you for the tip!)

I expect the OP loaded up on a number of Hilton Amex cards to have the points for the trip? Would be interested to hear what card(s) she plans to retain and which she will dump.


Hi Reed – I have the Aspire now and plan to keep it long term because of the benefits and ongoing earning.

Previously I’ve had the Hilton Business but it didn’t make sense to keep when I got the Aspire. And a for a few years I had the Hilton Surpass (no longer available – it became the Ascend).

Hi Jasmin,

Thanks for the great write up!

How long did it take for you to save up all of those Hilton points and what card bonuses did you get to get there?

I haven’t applied for any Hilton cards yet but would like to stack as many as possible. Can I get one of each card and stack the bonuses?




Hi Keola – Hard to put a firm timeline on it because I’ve had one Hilton card or another for many years and accumulate points from regular spending and paid stays, too. You can earn the bonus on each AMEX Hilton card just once. In the past ~14 months I’ve earned bonuses from the Aspire and Hilton Business so that was a big chunk right there. In fact, if you have a partner (Hilton lets you pool points for free), each could get the Aspire (150K points X2) and one could get the Ascend or the Business a little bit later – you’d have more than enough points right there for this particular trip (or any 5-night stay at a top-tier Hilton resort).