When I first started planning our visit to Oahu, we were only supposed to stay there for two nights. My main goal was exploring the island of Kauai, which is one of my favorite spots in the whole world. But then, Hawaii has morphed into a stopover on the way to Japan.
Since we are scheduled to fly from Honolulu to Osaka, it made the most sense to base our entire stay on Oahu. As much as I tried to rationalize splitting our four nights between Kauai and Oahu, it would probably push my poor husband over the edge. And in the end, we really wouldn’t do either island justice.
Plus, the more I researched Oahu, the more it appealed to me. There is truly something for everyone here. See Nancy’s post for top ten family activities on Oahu. We have only spent a few hours on the island during a layover and didn’t really venture beyond Pearl Harbor. It’s time to change that.
Now I just needed to decide where we would stay. I have narrowed it down to three possible options, and hopefully my reasoning will help those of you going through the same type of dilemma.
Last year I wrote a post with reasons why I should/should not splurge on Aulani. I won’t rehash the whole thing, but let me summarize. Basically, there is no way I would ever pay $600 per night to stay in Aulani. Obviously, I would never tell someone how they should spend their money. How obnoxious would that be, right? But the regular price tag for me personally is a deal breaker.
Nancy’s photo of Aulani
However, the rate becomes somewhat palatable when booked through DVC rental store (between $325-$375 per night). For this price you get free Kids Club, tons of activities, a family-friendly beach and so on. Of course, you also get crowds and a fairly cramped room to share with your kids.
But the biggest issue for me was the location. Originally, I was planning to stay in Aulani for two nights and only visit Pearl Harbor. With four nights, there are other things I want to do on the island. I have my heart set on Kualoa Ranch, and that’s an hour one-way drive from Aulani. Ditto for Hanauma bay.
We could stay in Aulani for two nights at the end of the trip and focus on amenities, but that just complicates things. And this trip is already complicated enough, with Japan addition and all. We will be staying in at least six different places as it is.
Plus, honestly, while I have no doubt my kids would love Aulani, I’m not sure my husband and I would. And if I’m paying $375 per night for hotel, I better be sure I will love it. We are not Disney fanatics, so this is just another crowded resort. If my kids don’t know about Aulani, they won’t know what they are missing.
As much as I try to make my kids happy during trips, the adults always get priority. Why? Because we are the ones paying! Don’t tell the mommy-shaming police.
And so, Aulani was out.
From a points collector perspective, this area makes the most sense. It has the highest concentration of hotels and is fairly central to most of the activities on the island. Plus, there is a beautiful beach right there. As a bargain hunter, you will have a tough time here, but there are a few deals to be had. Namely:
It costs 15,000 Hyatt points, so it’s eligible for renewal certificate from Hyatt co-branded credit card.
It costs 12,000 Hyatt points per night, and you get free breakfast.
It costs 15,000 Wyndham points per night, though availability is scarce. You get a condo unit with a separate bedroom, plus sofa bed in the living room. IMO this is the biggest points bargain in Waikiki, but good luck finding award availability.
The cost is 15,000 Wyndham points per night. You get a studio unit, with a king bed and a sleeper sofa. Award availability is very good, unlike the other Wyndham property on the list.
It costs 40k IHG points, so it’s eligible for annual renewal certificate.
Not exactly dirt cheap, but! For 70k Hilton points you can get a 1-bedroom suite with two queen beds and a sleeper sofa. There is also free breakfast and evening reception. All in all, this is a solid value for families, especially if you are swimming in Hilton points or have a few weekend certificates to spare. It’s also listed as a resort, so you can utilize your $250 credit from Amex Aspire card.
As someone who is not swimming in cash, I found Waikiki area to be quite appealing because it would allow me to utilize hotel points instead. I had some Wyndham currency and a sizable Hilton stash that would come in handy. The problem? I would have to spend my long-awaited Hawaii vacation in crowded Waikiki beach, sharing it with thousands of other tourists.
The more I researched Waikiki, the more I knew this was not the right place for us. I’m sure we would have fun, but there had to be a better option, even if it meant paying cash.
The other day, I was talking to my husband about our previous trips to Hawaiian islands. I was reminiscing how we had to stay in super cheap studio rentals on someone else’s property because that’s all we could afford. His response: “That was my favorite part!”
Our tiny cottage that cost only $65 per night all-in
The thing is, I really liked it too. We were in a local neighborhood, away from all the fancy resorts. But it allowed us to experience a slice of real Hawaii before AirBnB was cool. We were never really the cool kids, we just couldn’t afford anything else.
No money for luau, but we got to watch the hula dance for free from a nearby restaurant (Hula hacking?)
Even though our financial situation is better these days, staying in a local area still holds the most appeal. So, I knew what I had to do.
I wanted a Kauai-esque experience on Oahu, and this led me to Kailua, located on the East side of Oahu. While birds-eye view of Waikiki area looks like this:
Here is the town of Kailua:
It doesn’t hurt that Kailua beach is one of the best in the world. I found this photo of scenery in a neighboring town of Kaneohe, and asked my husband what it reminded him of:
He said that this was definitely a photo of Kauai. Nope!
There was a problem, however. It’s not that easy to stay in Kailua, not legally anyway. Tourists won’t get arrested for renting from an illegally-operated AirBnB owner, bit there are a lot of other issues. Oahu has just passed a new law meant to curtail the proliferation of illegal vacation rentals, so you may pay for a place only to find that it’s no longer operating when you get there.
How to know for sure if your vacation rental is legal or not? Look for NUC (nonconforming use certificate) number in the listing, which is one of new law’s requirements.
This is a complicated issue, and I can honestly see both sides. But for me personally, it was a no-brainer to comply with local laws for ethical reasons. Fortunately, I was able to find a legal vacation rental located within a short walk from Kailua beach. There aren’t that many in the area, but they do exist, mostly bed-and-breakfast type as well fancy oceanfront properties.
The price of the one I found on Homeaway.com was $300 per night all-in, a whole lot more than $65 we paid back in the day. Still, the unit has two bedrooms with A/C, a kitchen, plus washer and dryer. There are no resort amenities, but there is a spectacular beach within walking distance.
More importantly, it will help us experience Oahu the way I want to experience it. Kailua is within a thirty-minute drive to the airport, Kualoa ranch and Pearl Harbor, so it’s pretty convenient for what we want to accomplish in the area.
The point of the post is not to trash Aulani or Waikiki area. I haven’t stayed in either one, so not really qualified to give an opinion. If our stay in Hawaii was longer and if we didn’t plan to fly to Japan afterwards, I would totally consider Aulani.
Likewise, if my financial situation didn’t allow splurging on a vacation rental in Kailua, I would burn my points on a Waikiki hotel and wouldn’t think twice. These are first-world-problems, amigos.
But Hawaii is special to me and worth the splurge despite my middle-class status. Maybe I’m just being nostalgic, but staying in a local neighborhood (again) feels right. I would rather save my hotel points for an airport stay or a road trip where I just need a place to sleep. I’m sure my kids would prefer pools and other amenities of a hotel, but that’s what our local Florida getaways are for.
Readers, where do you usually stay while visiting Oahu?
Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.