We were not chasing a $399 Hawaii deal since we live here, nor were we shopping for flights or hotels. We clicked the TravelZoo headline because it looked like the kind of promotion designed to pull people into something else, and we wanted to see exactly how that process worked from the inside. On the surface, it was framed with round-trip flights (basic economy with a stop), three nights at a 4-star Waikiki hotel, and all taxes and fees. It sounded just plausible enough to test rather than dismiss. Well, to be honest, we were skeptical but curious. And we wanted to report to readers.
Before we could even test the deal, we had to sign up for Travelzoo’s new Club, the latest twist for the failing legacy travel deal company. That meant paying the $1 trial fee for 30 days and handing over our credit card for the $50 auto-billing later. We then went looking for the $399 Hawaii vacation they were promoting and quickly discovered that the price itself did not exist anywhere on the site.
Where the $399 deal goes missing.
The first thing that stood out was how hard it is to even locate the Hawaii deal Travelzoo is promoting. It does not appear on the Travelzoo homepage after you sign in, it does not show up under beach destinations, and it is not featured anywhere despite being the headline of a national press release.
To find it at all, we had to search Hawaii specifically and click through to a booking page run by Great Value Vacations, which makes clear that Travelzoo is acting as a storefront rather than the company actually selling the trip at all. That extra layer already undermines the impression of a simpler, headline-driven offer.
After reaching that booking page, the advertised $399 price still never appears at any point in the process. We searched month by month and date by date across every date offered during spring, summer, and fall, and did not find a single $399 option. We even checked further for all West Coast cities offered, but again, no $399 anywhere.
What the pricing calendar actually shows.
The real pricing calendar tells a very different story than the marketing language suggests. The lowest price we found was $499 per person from Los Angeles, where that price appeared on only six dates total, with two in April and four in May.
Checking all available dates makes the gap between the headline and reality impossible to miss. March pricing starts at $574, April drops to $499 on just two dates, May offers $499 on four dates, June jumps to roughly $849, July shows no availability at all, August prices start at $774, September comes in at $624, October $649, and November rises again to $699.
Most of the calendar sits well above the advertised price, often by hundreds of dollars. The $499 figure is the rare exception, not the norm, and even that is $100 higher than what Travelzoo is advertising to get people to put up their credit card to enter behind the door.
That difference matters because the $399 number is doing all the work. It is the hook that gets people to click, sign up, and enter payment information before they have any realistic sense of what the trip will actually cost. You don’t get to look at the offer, dates, airports or anything before putting your credit card on the line.
How the membership charge takes over.
To see the deal, you must join the Travelzoo Club, which offers a 30-day trial for $1. During that signup, your credit card is captured immediately, and unless you cancel, the membership automatically converts to a $50 annual charge.
The refund window is tighter than it looks and is one of the most important details in this entire setup. You have 14 days from the start of the trial to request a refund on the annual fee, which means half of the trial period is gone before your ability to undo the charge is set to disappear.
During the signup process, we found nothing obvious explaining how to cancel, where to cancel, or what steps are required to avoid the $50 charge. We will almost certainly cancel before the end of the trial, and are hoping not to end this with a credit card dispute. We’ll report back on how that process actually goes.
What you are actually getting for $499.
The Hawaii package itself is fulfilled by Great Value Vacations, not Travelzoo. The trip includes round-trip airfare from Los Angeles to Honolulu with one stop each way on Alaska Airlines in basic economy, plus three nights at the Outrigger Waikiki Paradise Hotel in a standard room.
The included flights had a stop in Seattle in both directions, which would make for an extremely long day flying from Los Angeles. There was an option to upgrade to nonstop, however.
The Outrigger Waikiki Paradise is a legitimate Waikiki property, formerly the OHANA Waikiki East, located near the beach and the International Market Place. Calling it a four-star hotel is generous by our standards, but it is a solid mid-tier option that many Hawaii visitors will recognize.
Recent guest reviews consistently praise the hotel’s location and staff but mention small rooms, tiny bathrooms, and occasional maintenance issues, including inconsistent hot water. That profile fits mid-range Waikiki hotels, but it may not be the four-star experience guests expect, as the marketing implies.
Our recent Google price check shows standard rooms at the resort starting at $158 per night before resort fees and taxes. The TravelZoo package includes a waived resort fee that normally runs $40 to $50 per night, plus tax, creating real savings on the hotel portion if you can make the limited dates work.
At $499 per person for two travelers, the total package price comes to $998. A reasonable breakdown puts basic economy airfare in the $350 to $400 range per person, leaving roughly $100 to $150 per person for three nights of hotel.
Why this still feels like a trust issue.
Travelzoo is not really selling a Hawaii vacation here. Instead, it is selling a paid membership to its massive legacy email list built during a very different era of online travel. The company is under clear financial pressure, with its stock trading in the mid-$5 range after falling sharply from $26 in the past year, which helps explain why this push is happening now.
This feels less like a comeback and more like a liquidation of trust, using a price that does not exist to pull people into an auto-billing membership. The deal has limited value on a few dates, but the promise that initially drew people in simply wasn’t real.
If you clicked the $399 Hawaii headline, paid to join, and went looking, did you find something different from what we did, and did you see a clear way to cancel once the clock started ticking?
Photo Credit: © Beat of Hawaii. Sunrise on Waikiki Beach.
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