If Only I Could Take My Family to Hawaii


Our if only… series continues with a frequent reader thought. “If only I could take my family to Hawaii for free or at a reduced cost.”  We get it. Taking a family all the way to Hawaii and then having to get lodging is expensive. Once you get there, you still need a rental car and then food is expensive. Wouldn’t it be awesome to use points and miles for your flights AND your lodging? We are here to tell you that you can do it! And we just did it last May when Alex paid all of $55 for a trip to Maui for her family of six!


If you want to take your family to Hawaii, you need a plan and you need to start about a year out from when you want to go if you want flights and lodging. If you can fly Southwest to take your family to Hawaii, it will probably be your cheapest option. Especially since you will get free checked luggage. I recommend you take some snacks in an extra bag for your family because food is expensive no matter which island you choose.

If you can get the Southwest Companion Pass before you go, that will save on flights too. I would for sure try and get a Southwest personal and business card as getting one of each of these cards is the easiest way to get the pass.

You can also use credit cards that earn you Ultimate Rewards because they transfer to Southwest. Read our article on how to get flights to Hawaii for more suggestions. It will probably take you six months and two signup bonuses to earn enough points and miles for flights.


Sometimes, it makes sense to get an Airbnb for family lodging. In this case, you may want to get the Capital One Venture X card. For the first year, you get an Airbnb or VRBO credit of $200 which will help. You also will earn 100,000 Venture Miles after spending $10,000 in six months. This could “erase” $1,000 of your Airbnb expense charged to your Venture X card. Just this one card and the $200 credit could pay for your lodging at an Airbnb.

Hyatt has some amazing properties on the Hawaiian islands so one of the World of Hyatt credit cards is another good option. Marriott also has great properties in Hawaii so a Marriott Bonvoy credit card or two could help. Just be sure you are signing up when the welcome offers are high.

Reader Success Stories

We have a couple of reader success stories where people have shared how they took their families to Hawaii. Learn from trips that Trent and Cami took. You can also read about some of our stories to Kauai and Maui.

Bottom Line

Never again say those words, “If only I could take my family to Hawaii”. It’s totally possible. Start mapping out a plan to do that today. We are glad to help you with that plan. Can’t wait to see pics of you and your family on the beach!!

sun coming through clouds on water

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