8 Night Luxury Hawaiian Resort vacation for FREE!

Aloha! I recently spent 3 nights on the beautiful island of Kauai followed by 5 nights on ever-growing Hawai’i (Big Island) and it was a very memorable vacation as my flights, 8 night stay at the Grand Hyatt Kauai and Hilton Waikoloa Village Hawai’i costed me effectively under $40 out of pocket. While there was a bit of planning and timing involved, it was an amazing and relaxing experience overall.

Booking my flights for $39

I booked my flight on Hawaiian Airlines and they are a transfer partner with American Express. That gives card holders the opportunity to transfer Membership Rewards points to Hawaiian Airlines 1:1 with a tax offset. At the time of transfer, there was a 25% promo which meant I had the opportunity to transfer at 1:1.25.

In my case, I was looking to book three flights: One to Kauai, Kona and back to Seattle between October 28 to November 5 and the total cost for multi-city tickets was $900 in main cabin. This was initially a buzzkill as these were really expensive flights.

Thankfully, the same legs costed a total of 47,000 Hawaiian miles + $16.8 in taxes/fees. I ended up transferring 38,000 Amex MR points at a 25% promo. This effectively netted me a 2.3 CPP value on my points – which is slightly lower than what I was able to get last year for my direct roundtrip flights to Maui.

Free 3 night stay at Grand Hyatt Resort Kauai

I am a Hyatt Globalist and have benefitted greatly by having status with said brand. I wanted a great stay and experience with as many included amenities as possible. The Grand Hyatt Resort is one of the best resorts on the island of Kauai and it also offers a Club Lounge which meant I could get free breakfast, snacks and dinner on the property thanks to my Globalist status in addition to free valet parking ($52/day) due to booking a reward stay.

Redemption rate

Accordingly, I booked a standard stay for 3 nights for 75,000 World of Hyatt points – most of which I earned from my Chase World of Hyatt Visa Credit Card and additional cards I opened at the tail end of 2022 to restock points.

I was upgraded to an oceanfront room upon check in thanks to my status and the same stay would’ve costed a whopping $4,482.07 (and still not included access to the club lounge).

As this was my birthday trip, the hotel had provided us with wine, snacks and drink coupons for our stay which was a lovely gesture.

Surprising turn of events

On day 2 of our stay, we had to file a noise complaint because of some renovation work nearby which caused us minor disturbance during the day (and it stopped immediately) and management issued us a $100 property credit and 30K points. We took advantage of the $100 credit to rent tubes to float on the lazy river and have a Hawaiian taxed (i.e. overly expensive) dinner on our last night. I was also enrolled in a Hyatt bonus offer that gave me 3000 WoH points on 3 night stays. We effectively spent 42K points for three nights.

All in, I had an unexpected ROI of ~11CPP on my Chase/WoH points.

Unfortunately, this property now charges 30K points per night vs the 25K/night I redeemed which, adjusted for newer rates, still would net you 5.1CPP – an amazing value if you ask me given the size, location and activities on the property.

Free* 5 night stay at Hilton Waikoloa Village, Hawai’i

I have Gold status at Hilton thanks to my American Express Platinum card and had over 600K Hilton Honors points thanks to the Hilton Honors Surpass and Business credit cards I had opened in the past year along with a few well timed transfer bonuses from AMEX and this seemed like a good opportunity to redeem them.

The average cost per night was $450+ taxes and fees for a standard room at the Palace Tower which is the older of the two towers at the resort – which also shares its land with the Hilton Grand Vacations Ocean tower. After factoring in resort fees and taxes, I was potentially looking at a bare minimum of $2,700 for 5 nights. While there were other resorts in Waikoloa village like Marriot – which I actually stayed at when I visited Hawai’i back in 2017 with my parents – who at the time paid $1400 for three nights and costed roughly $2500 for 5 nights in 2023, I did not have the required points and the properties were much smaller with fewer amenities to offer.

Redemption rate

One great benefit of booking 5 nights using Hilton Honors points (as covered in my Maldives bookings articles) is that the 5th night is free and you are exempt from paying resort fees or taxes on the booking. Standard reward rates for the property were 75K HH points and I only needed 300K HH in total. The stay yielded 20K HH points from the spend on property for a net 280K HH redeemed.

Just on the room itself, the ROI on the HH points was close to 1.1CPP which is pretty fair considering the average redemption rate is 0.5-0.7CPP.

Credits and optional costs

I was upgraded to the newer and nicer Makai tower with bigger and modern rooms a week prior to check in however it was a resort facing view. Resort view rooms in Makai tower typically start at $475+ taxes and while we did get a five night stay for free, we opted to take a $40/day upgrade to an ocean facing room for 4 nights (since we checked in really late on the first night).

In addition to that, since we were renting a car, we also had to pay a $48/night self-parking fee – which you can honestly avoid if you just do day rentals with National at the hotel (which bypasses the parking fee) – you do have to return the keys at 4pm though. Hyatt does not charge parking on award stays but Hilton does.

Thanks to my Hilton Gold status, I had a daily $18/person F&B credit which honestly wasn’t a lot but covered the cost of burritos, wraps and sandwiches from the marketplace at the Makai tower which came in handy on day trips or breakfast. Everything else on the property is overpriced and honestly not worth it. We mostly ate local.

Final Thoughts

Now that the my stays and flights were covered, I was able to really enjoy my vacations as I had more money leftover in my budget towards experiences – most of which I put on a recently applied Chase card which has a 120K point Sign on Bonus – which I will redeem for travel in 2024!

So, when are you planning your trip to Hawaii?