A little luxury at the Grand Wailea (or when using points + cash pays off)

As anyone who’s been there or looked into going there knows, Hawaii isn’t cheap. Even though I found a cheap flight, I knew the trip to Hawaii would not be an inexpensive one. Trying to stay on somewhat of a reasonable budget, we booked a cheap 2.5 star hotel for the first few nights of the trip. Since we planned to be out exploring most of the time, we figured why bother wasting money on expensive lodging? But for the end of the trip, we wanted to splurge a little to get a little taste of resort luxury.

Although I’ve been hoarding my points over the past few months as I work towards hacking a European trip for my family, I had a decent stash of Hilton points that I knew I wouldn’t need so I checked into what options might be available on Maui. Currently, the only Hilton on Maui is the Grand Wailea, a Waldorf Astoria resort. As most know, Waldorfs aren’t cheap, and this place is no exception. For the dates we were going to be there in mid-February, the lowest price room was going for just under $600. Even looking at the points, they were asking for a whopping 80,000 per night! No way I would waste all those points on one night. But scrolling through the rate options, I noticed that they had a points and cash option available. They were asking 32,000 points and $150 per night for the lowest level room.


Points and cash example for sample date

Let’s do the math on this for a minute. Let’s say that the points and money option split the cost in half between the points needed and half the actual cost of the room, which might be your logical deduction. If that were true, this room should have been 40,000 points and almost $300 for a night. Instead, they were asking for 32,000 points and $150. What?! Sold! With all my extra Hilton points laying around, 32,000 was a drop in the bucket and $150 for a night in a luxury hotel on Maui is just unheard of! To top it off, that $30 resort charge per night they mention in the image above isn’t tacked on if you book the room on points OR on points and money. Another win!

So of course I booked it. But was it worth it? Oh, yes.


Looking out to the ocean from the hotel

After a few days of budget-friendly lodging, we pulled into the resort and dropped the rental car with the valet. The Grand Wailea doesn’t have a self-park option, so be prepared to pony up the $30 for valet parking. Despite the cost, the convenience was welcomed, as we were quickly ushered into the open air lobby and towards the check-in desk.


Entrance to the open air lobby

I had booked us in the lowest price room, but was pleasantly surprised to be told that we had been upgraded to a renovated ocean-view room. I have Silver (low level) status with Hilton because of my Hilton Citi credit card, which may have been the cause for the upgrade. Whatever the reason, I was pretty excited. A balcony overlooking the ocean at a Walforf Asotria in Maui for $150 a night? Not too shabby.

After check-in, we were greeted by a woman dressed in traditional Hawaiian garb, offering up leis. The women were given beautiful fresh flower leis picked from trees on property and the men received the more masculine dried macadamia nut leis.


Lei and welcome packet

The room was nice, although not quite as luxurious as I might have expected. Neutral-colored carpets and walls gave it a rather bland look, but it was fresh, clean, and modern, so I really didn’t have a complaint. The bathroom was huge. In fact, it was likely bigger than our previous hotel room. There was a large soaking tub and a separate walk-in shower, with a huge vanity and room to spare.


Looking out to the balcony from our room

Of course, the highlight of the room was the balcony and view overlooking the ocean. Off in the distance, we could see Molokini crater where we had snorkeled the day before. We thoroughly enjoyed a $65 room service breakfast out on the balcony on our last morning. Yes, $65. And it was amazing.


View from our room

The grounds of the Grand Wailea were impeccable, with beautiful landscaping and details. Being a huge resort, there was a never ending supply of things to do and places to eat or drink. The pool complex was huge, with a number of different options geared towards children or adults, including several waterslides and a water elevator, taking people from the lower pool to the top of the waterslides without having to get out and walk.


Grand Wailea grounds

Although almost every minute of the stay was wonderful, the day of check out left me truly impressed. We had a late flight out that night, around 11pm, and had decided to just lounge at the resort until it was time to leave. The bellhops took our bags to store for the day and we were told we could keep our room account open until we left, allowing us to charge incidentals to the room throughout the day without having to worry about carrying around cash. I loved being able to do this, although I’m sure they do it because it ultimately works out to their advantage, with $15 cocktails and ample poolside service.


Mmm… $15 Maui Mule

Regardless, it was a relaxing way to wind down our vacation and I sure can’t complain about convenience, even if it did hit my wallet a bit.

After lounging most of the day away, we had hoped to change clothes and maybe get a little less stinky before dinner and the almost 20 hour flight back to the east coast. We stopped by the bellhop stand to get our luggage and were directed to the front desk to request a key for the hospitality suite. Hospitality suite? Yes! I was just hoping for a bathroom to change in, but instead we were given the key to a mystery suite. Walking up to the room, we looked at each other in surprise as the entrance had double doors. You know you’re in for something special with double doors.

The suite was huge! It had a full size living and dining room area along with a walk-in kitchenette. There was a newly renovated bathroom with a huge shower stocked with piles and piles of toiletries and towels. The balcony off the suite wrapped all the way around and overlooked the ocean. This was the craziest place I’ve ever been offered for freshening up and it was all ours for 45 minutes.


The hospitality suite

All cleaned up, we opted for dinner in Bistro Molokini, a relatively affordable restaurant (well, at least compared to the others) with wrap around windows offering stunning views of the sunset. It was a great way to end our stay.


Our view from dinner at Bistro Molokini

We were sad to say goodbye to the Grand Wailea, but they had one little finishing touch for us. As we pulled out of the resort in our rental car, I looked down to see two ice cold bottles of water sitting in the cup holders. The valet must have put them in before delivering the car to us. It was a small gesture, but little things like that are what make a luxury resort truly luxurious.


One last sunset at the Grand Wailea

For $150 a night, I’d say that was a pretty damn good value. Of course, we ended up spending more than double that on food and drinks, but we’ll just disregard that fact. The moral of the story is to always check out those points and cash options. They might just be a better bargain than using points or cash alone and they might just give you an amazing taste of luxury for a night or two.




  1. I would love to stay at one of the luxury resorts in Hawaii but it has been 2 star hotels and hostels on my last two visits (and my upcoming one). One day I will definitely splurge :)

    • I wish I could afford it for more than one night, and even then it was only because of the points and cash option. I can’t imagine how people dish out $600/night for a week or more!

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