Airbnb: Hawaii Travel Plans Must Start With Hotel. It's True

Airbnb Says Hawaii Travel Must Start with Accommodation. Why It’s True

When you begin Hawaii travel planning, do you book the airline, hotel, or rental car first? Conventional wisdom says the first stop is an airline ticket. But that was pre-Covid, and now everything has changed. Brian Chesky, Airbnb’s CEO, said we have it all wrong this week. And we say he’s right. Here’s why.

Hawaii hotels or vacation rentals can cost 3x to 6x the cost of airfare.

Chesky said that we have our focus on flights wrong and that we should be going from Hawaii inspiration first, to Hawaii accommodations next, and then to airfare. Now Airbnb has a pointed view since they don’t sell airline tickets, but that being said, let’s compare the average cost of an airline ticket and accommodations to help evaluate his point.

According to Chesky, “I actually think the top of the funnel isn’t flights, it’s inspiring people where to travel to. That’s the first decision you make. Where should I travel?”

The common thinking was that airfares were so variable from day to day and season that we first needed to find airfare. We have been guilty of booking flights and not even noticing what the accommodations situation would be on arrival for days, weeks, or sometimes even months. Fail.

The cost of accommodations is a driving factor in Hawaii vacations.

Hawaii has the highest hotel accommodation rates in the U.S. In the last quarterly data, Hawaii led all other markets with average daily rates of $362. Miami and Phoenix followed Hawaii. For a 7-night average Hawaii vacation, including all taxes and fees, that’s likely to amount to $2,990 or more. And if you’re staying in South Maui, Wailea hotels are getting an average daily rate of $1,000, such that a 7-night stay with tax could amount to $8,260 or more.

Hawaii airfares remain relatively cheap.

Economy airfares to Hawaii remain very low, especially in the most competitive and highly traveled west coast markets. It is easy to score airfares of about $300 RT, including all taxes and fees, and sometimes significantly less. So looking at two people, the average cost might be $600. Or, being generous and considering less competitive markets, let’s double that, and say the price for two is $1,200. Thus the airfare is at most about 1/6 to 1/3 of the cost of accommodations.

How much do Hawaii hotel rates vary? A lot!

We did a few price comparisons to illustrate the situation. First, we looked at Andaz in Wailea. A high-end property that has highly variable rates. We found starting rates as low as $754 per night this fall. But if you move your vacation from the fall to January, some nightly rates are as high as $1,898. For the very same room. These before about 18% taxes and other fees.

We checked the Four Seasons Resort Wailea and found fall rates as low as $967. But switch to early 2023, and some of their nightly rates were as high as $1,898. For the very same room. Plus the taxes and fees.

We also checked the lower-cost, well-rated Aston Maui Hill (Condo) Resort. There, fall rates started at $490 a night. But in January, rates on those same rooms began at $1,098, or more than double. These rates, too, are before taxes and fees.

And it isn’t just that rates vary by season. They can also vary within any period just by the day of the week. Hotels, like airlines, now have dynamic pricing and they adjust their prices on a daily basis.

Bottom line – pick your accommodation before airfare.

Our travel planning has shifted towards accommodation-first planning and away from airfare-based planning.

Do you want to stay at Wailea, or would you be equally happy on the spectacular beaches of West Maui, for example?

The cost of Lahaina, Kaanapali, and Kapalua hotels is about half, on average, of Wailea hotel rates.

Oahu hotels have the lowest average daily rate of $244 for Q1 2022, which was only up just 6% compared with pre-Covid. This is one of the best values in Hawaii accommodations.

If you book on the hotel website rather than on Expedia or Booking, you might save money or provide some perks. It simply reduces the hotel’s cost.

Check into hotel packages for options including parking, daily breakfast, and included resort fees.

Hawaii is a great place to redeem travel points from loyalty programs or credit cards.

By all means, consider and check rates on Hawaii vacation rentals, which include a kitchen and can further help reduce food costs.


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9 thoughts on “Airbnb Says Hawaii Travel Must Start with Accommodation. Why It’s True”

  1. Surprised you barely mention vacation rental properties. Many times you can get a one or two bedroom condo for the same or less daily rate as hotels. Also, as you said, you can save big on meals if you desire. Even breakfast and lunch can be pricey. Dinner prices at restaurants have also gone through the roof so making dinner at a vacation rental a few times during your stay can save big money. For a group that needs multiple hotel rooms, vacation rentals are a no brainer IMHO.

  2. Aloha BOH Bros

    Might be off subject a little, but lots of reports out of Maui how there’s been a sudden drop off of tourism the last couple weeks more then normal for this time of year. On other sites there’s been many posts advertising fall & early winter vacation condos at discounted prices. Plus individuals who have non-refundable condos booked looking to unload them at below what they paid to cut loses.

    Have you seen any of this if so might be the Hawaii tourism bubble bursting.

    1. Hi Richard.

      There’s definitely softening of the intensity that we’ve had. Not sure that many are complaining about that at the moment, either residents or visitors. Flights vary from being mostly empty to being at full capacity.


  3. We only fly into Kona. Airline tickets on Alaska Airlines are realy stable and we use miles and the companion ticket. So that is reasonable. Rental cars are very high right so I book through Costco and cancel if the price drops. Cabins off the beaten path are reasonable and even the condos if book ahead on non holiday times. We buy food at Costco and eat out only a few times. We hike and snorkel for free not tours. Condos seem high but then look at everywhere else along a coast line around the world. Get the best deal available and save money other places in your life. Time keeps slipping into the future.

  4. We just discovered this. Got $105 Maui direct each way in Feb. was blown away by the hotel and condo prices post COVID. Ended up buying a timeshare resale at our fav place. Will save us $ in 3 years. Being that we come once a year, made sense. Never thought I’d buy one.

  5. Mahalo for this info. My spouse and I don’t travel that much and I tend to “bundle book” (airfare, hotel, car on one website) as it’s been less confusing for me. I’m thinking I might have to learn to embrace at least comparing separate booking to see if it’s a better cost! I’ve noticed that the hotel is by far the most expensive component now.

  6. If AIRBNB was a travel agency, they could offer Full Package. Air/Hotel/Car.
    Car rental is not mentioned in this article. which can be $150+day for a compact, Depending on the island.

    I agree, look at accommodations first. Honestly, I would use Oahu as a hub and stay outer islands 1-2 days. Housing must include kitchen and laundry.

    Mahalo for visiting.

    Local Resident

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