How We Take Our Family to Hawaii for Almost Free

Once upon a time, taking my family to Hawaii felt like a dream. Hawaii was for rich people, and we ain’t rich.

But back in late 2019, during a major Southwest sale, I realized we had just enough points to fly our family to Oahu. We were a family of five at the time, but one of our kids was still a lap child, so we only needed four tickets. I thought I was BALLIN’.

We redeemed basically every Southwest point we had, found a cheap Airbnb, packed our bags, and in early 2020, before the world caught on fire, we took our dream vacation to Hawaii. When we got there, I almost immediately remember thinking, This cannot be a once-in-a-lifetime vacation. I’ll sleep in a tent on the beach if I have to, but we HAVE to come back. We have to see the other islands too!

Fast-forward to 2026, and we’ve now been to all four major islands, some more than once. We’ve done those trips for a fraction of what they would have cost us otherwise.

How? I learned how to strategically open credit cards, meet the minimum spending requirements using expenses we were already going to have, earn the welcome bonuses, and redeem those points and miles for flights, hotels, rental cars, and other travel expenses. Then, when it made sense, we did it again.

So the question I get ALL the time is, “How do I do this too?” And usually right behind it is, “How long would it realistically take me to earn enough points for a Hawaii vacation?”

There are a lot of variables, of course, but if I had ZERO points today and Hawaii was my goal, here’s the general strategy I’d consider.

A Crash Course: How I’d Use Points for Hawaii

Flights: I’d Start With Southwest

If Southwest serves your home airport and your Hawaiian destination, it would absolutely be one of the first programs I’d look at. Southwest award prices vary based on the flight, date, demand, and cash price, so there isn’t one set number of points you’ll always need. But I’ve seen some fantastic award pricing between the western U.S. and Hawaii, especially when Southwest runs a sale.

Another HUGE reason I like Southwest for families is the Companion Pass. A Companion Pass lets you designate one person to fly with you on Southwest for just the taxes and fees whenever you book an eligible flight, whether you paid for your own ticket with cash or points. More on that here.

Lodging: Hyatt, Marriott, or Flexible Points

Next up: where are you going to sleep?

If you love a traditional resort experience, I’d look at hotel programs like World of Hyatt and Marriott Bonvoy, especially when their credit cards have elevated welcome offers. I’d also consider flexible points that can be transferred to hotel programs. For example, eligible Chase Ultimate Rewards points can currently transfer to both World of Hyatt and Marriott Bonvoy.

If you prefer vacation rentals instead of hotels, I’d look at flexible rewards such as Capital One miles. Eligible Capital One Venture miles can currently be used to cover qualifying travel purchases made within the previous 90 days, and Capital One also allows certain vacation rentals to be booked through Capital One Travel.

Rental Car: Don’t Forget This Part

Yes, I’m putting the rental car in the Hawaii budget. Do you technically need one on every island and for every itinerary? No. But if it’s your first trip and you actually want to explore, I highly recommend budgeting for one.

Please don’t fly all the way to Hawaii and never leave the resort unless that is genuinely the vacation you want. There is WAY too much beauty outside those resort walls.

Again, flexible rewards like Capital One miles can be really useful here because qualifying rental-car purchases can be covered with miles. And don’t sleep on Atmos Rewards, the loyalty program shared by Alaska Airlines and Hawaiian Airlines. This surprises a lot of people, but Atmos Rewards points can be redeemed for more than flights. The program currently allows you to redeem points for hotels and rental cars, too.

Okay, But How Long Would This Actually Take?

Here comes everyone’s favorite answer: it depends.

Your timeline depends on how much your household normally spends each month, how many people you’re traveling with, how long you want to stay, what kind of accommodations you want, which cards you’re eligible for, the welcome offers available when you apply, and how aggressive or conservative you want your credit card strategy to be.

For a family of five like mine with roughly $4,000–$5,000 per month in normal expenses that can responsibly be paid by credit card, I think building a Hawaii points strategy over approximately six months can be realistic in the right circumstances.

But I would never promise that someone can earn an entire nearly free Hawaii vacation in exactly six months. Availability changes, welcome offers change, award prices change, and most importantly, you should never spend extra money or carry credit card debt just to earn points.

That’s actually what I love most about this hobby: it isn’t one-size-fits-all.

Your strategy doesn’t have to look like mine. Maybe you want to move quickly, or maybe you want to earn points slowly over a year or two. Maybe your priority is free flights while you’re perfectly happy paying cash for a cute Airbnb. You can build a plan around your family, your spending, and your travel goals.

Bottom Line

The whole point of this is to show you that taking your dream vacation is absolutely possible—and it can cost WAY less than you probably thought. Maybe even close to free! If Hawaii is on your bucket list, visit my Best Offers page to see the cards and offers that can help make your dreams a reality. And if you’re still staring at all of this thinking, “Okay, but where do I actually start?” send me a message. I’m happy to help you figure out which direction makes the most sense for you.