Booking Hawaii: Part 3 – Hilton Hawaiian Village and Tending Reservations

Also see: 

I’ll go ahead and tell you the moral of this story: tend to your reservations.

After booking 4 flights to Honolulu, then adding my little brother into the mix, the final piece of the puzzle was to book the hotel rooms.

Step 1: The paid stay

When I visited Hawaii in 2013, my main takeaway was how much I’d like to go back to the Hilton Hawaiian Village and sit on my butt for a solid week. Poetic, right?

Yes, Maui was fun, and I loved the topography of the volcanic Big Island, but I’ll be damned if I didn’t love being in that resort. As schmaltzy, white-bread, and basic as it sounds.

Hilton Hawaiian Village

Just, yeah, gimme that!

My mom hasn’t traveled much. She’s barely flown. I asked if she wanted to island hop a bit, but she said she’d rather get to one spot in Hawaii and take it all in. Of course I knew just the spot…

Her husband (my stepdad) has limited vacation days, so she said they could stay 4 nights.

4 nights? Ding ding ding – Citi Prestige.

I decided to put my name on the room, add my Mom as a guest, and book it with Citi Concierge.


~$910 for 4 nights in Hawaii

That’s about ~$228 per night. Not bad, considering I’ll also earn a boatload of Hilton points, hopefully score an upgrade for them, and get a $20 dining credit each day I’m there (for being Diamond).

I immediately plugged the confirmation number into TripBam and settled into the knowledge that Hilton would probably have a sale at some point between booking and arrival.

(Here’s my write-up on TripBam.)

Sure enough, the rack rate fell to ~$200 per night.


Love it when rates fall

So I called Hilton and had them apply my new room rate to the same confirmation number. This is key.

Because all Citi sees is the confirmation number. And they have no idea what portion of the final charge is for the room and what’s for food and drinks. And I’m sure I’ll be adding plenty of Mai Thais to the rooms. 😉

My total charge fell to ~$1,046, but I’ll still get the original ~$269 credit. That brings my room rate down to ~$194 per night – a savings of ~$133 for making a quick 5-minute call to Hilton.

I used this same strategy at the Hilton Tokyo and can confirm I still got the original credit.

This is the importance of tending to your reservations – watch them and stay on top of it! $100 here, $100 there… it all adds up.

In the end, I’m paying ~$777 to bring my Mom and stepdad to Hawaii with me (flights were free). Happy to do it.

Step 2: The award stay

I’m staying 5 nights, so I’ll take advantage of Hilton’s 5th night free on award stays.

The Hilton Hawaiian Village is 50,000 Hilton points per night. But with the 5th night free, all 5 nights cost 200,000 Hilton points AKA 40,000 Hilton points per night. That’s pretty legit.



Booking this was as easy as plugging in the dates and pressing “Book.”

There were technically no award nights available, but I love the soft perk of Hilton giving Diamond guests enhanced award availability.

Between the Citi Hilton Visa (you can still get 75,000 Hilton points and no annual fee) and Hilton stays, it was easy for me to rack up the points. In fact, I already have 100K more, just from staying at Hiltons here and there.

Why I like Hilton

Hilton points get a bad rap, but consider this.

I can stay 1 or 2 nights at a mid-range Hilton and have nearly enough points for an award stay at a Hilton Category 1 (with 1 night) or Category 2 (with 2 nights).

1 night got me a Category 1 award stay

1 night got me a Category 1 award stay

2 nights got me a Category 2 award stay

2 nights got me a Category 2 award stay

Now look at this 3-night Hyatt stay:



An OK start toward one night at a Hyatt Category 1, I suppose.

But SPG takes the cake:



A night at the Aloft Winchester got me a staggering 270 Starpoints. This is why I don’t care about Starpoints. Man, they give you NOTHING for staying at their hotels!

I also did a proper analysis of Hilton Vs Hyatt status and found Hilton Diamond status to actually be more rewarding than Hyatt Diamond status. And I’ve scored some very nice upgrades this year with Hilton.

So I’m hoping lightning will strike twice and get me and my family an upgrade in Hawaii!

Bottom line

As per usual, this was some seriously geeky stuff.

I hope I’ve outlined my thought process for how and why I booked the hotel stays like I did. And showed how useful it is to stack money-savers like 4th night free with Citi Prestige and lower rates found on TripBam.

While we’re here, can I just say Citi Prestige has saved me over ~$2,500 so far year? And I have 2 more stay credits on the way. I won’t be surprised if I easily surpass $3K in savings with this card.

It’s not a piece of crap until July 23rd, 2017 – maybe. Depends on how much I’ll use the 4th night credit.

At any rate, it will be useful for at least another year, so I’ll pay my $450 and get $250 back after December. I can say with confidence this card is definitely worth $200 until next July.


So the next step is to get there and enjoy Hawaii. Can’t wait to post about it.

This is the first mother-son-family trip I’ve ever taken and I’m so excited. The beauty of combining good deals with points!

Have you booked a stay like this? Any other tips to add to the mix? 

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About Harlan

Just a dude living in Memphis, traveling, and working toward financial independence.

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  1. Why wasn’t the 4th free night 1179/4 for $295 when they only rebated $269? I thought until next summer they cut the total in half and rebate that.

    In other news, just got off the phone with Citi, and they approved me for the Prestige card 😀

    • Oh nice!

      They only give you back the cost of the 4th night. It’s the exact amount, not an average. So that credit is right.

      You will love the Prestige! 🙂

  2. With the upcoming changes to the Prestige, I’d be interested in seeing how using TripBAM impacts the credits! Thanks for the info! 😀

  3. I’ve been trying to figure out how to combine the Prestige 4th night free with a Fairmont 3rd night free certificate. It seems your example might provide a template.

    Please advise whether you think the steps below would work:

    1) Book 4 nights at Fairmont using Citi Concierge
    2) Call Fairmont to apply 3rd night free certificate
    3) Charge food/drink to my room such that final billing at checkout exceeds original discounted billing quoted by Citi Concierge

    • Very good! I think that would work nicely. I’ve heard of this working before – and I don’t think you need to exceed the amount quoted by Citi, actually. I just do that because I’m paranoid lol.

      You can also do this with SPG promotions and 4th night free (or even 5th night free promotions). Basically, as long as it’s a paid rate, it’s fair game to get a free 4th night.

      Let me know how it goes!

    • I’ll get more back from Citi Prestige. And I’d rather have 3X Citi TY points that what the earning rate is with an Amex card. No question.

  4. I was also at the Hilton Hawaiian village in 2013! I went back this year in March and hate how they got rid of the free breakfast with Gold/Diamond status 🙁

  5. Could you point me to some info that explains this part in a little more detail?
    “There were technically no award nights available, but I love the soft perk of Hilton giving Diamond guests enhanced award availability.”

    • @drew maltby sometimes when you search for award availability on the Hilton site it’ll say that none are available, but if you are a Diamond member it’ll actually show availability (you have to be logged into your Hilton account while searching), just one of their small perks of being a diamond member! When I was booking my trip in February to the Conrad at Koh Samui for this year November it was giving me a different pricing vs when I logged in as a Diamond member and searched it said something about Diamond Member special service no-minimum stay required and charged me much less points

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