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Hawaii on a Budget

Traveling to Hawaii can cost and arm and a leg, and most people choose to splurge because they think it is a once in a lifetime trip. Most likely, you’ll love it so much you’ll want to go back right away! There are ways to save without sacrificing luxury. Research is important if you want to ensure you are getting the best price for each component of your trip. 

In the words of LOST’s Jack Sheppard: “We have to go back!!”

I try to take advantage of airline miles and credit card points so that AT LEAST one of these will be free or almost free during a trip: LODGING, CAR RENTAL, and/or AIRFARE. For example on past trips I have gotten:

  • Minivan car rental on Big Island for 1-week retail price ~ $450: free with Thank You Points
  • Airfare RT from NYC to Kona and Maui back to NYC (open-jaw flight) retail price for 2 ~ $1850: free with United miles
  • 4 nights at the Andaz Maui Wailea retail price ~ $2000+: free with Hyatt certificates
  • 10 day compact car rental on Maui retail price ~ $430: paid $32 and the rest with Thank You Points
  • RT flights direct form NYC to HNL retail price for 2 ~ $1900: free with Hawaiian Airline miles

I have yet to hit the trifecta of free lodging, airfare, and car rental all one one trip. I almost got it for our Maui 2013 trip, but the airfare miles requirement was higher than normal, so I used a coupon for 25% off and paid for the flights on Hawaiian Airlines. (This coupon was part of my benefits when I signed up for the Hawaiian Air Visa Card from Bank of America).

For whatever components of a trip that I cannot get free, I will look for the best price possible. That may mean staying in condos instead of hotels, and learning to use websites such as Priceline and Hotwire. Sometimes package deals at Expedia and Travelocity etc. are ok, but I find that I can usually get a better deal by ensuring part of my vacation is free, and then booking the rest on my own.

Disney’s 5-star Aulani resort on Oahu. We rented DVC points in order to stay in a 1-bedroom condo at half the price of what it would normally cost


I have learned throughout my frequent trips, the benefits of staying in a condo or vacation rental as opposed to a resort. I like to have conveniences such as a washer/dryer, dedicated parking spot, full or partial kitchen etc. all at prices well below a regular resort or hotel. We don’t usually seek out the fanciest condos, but we do value a nice, clean, renovated space, as well as a good location. I use VRBO, HomeAway, FlipKey, and AirBnB to name a few sites where you can seek out condos by owners. Oftentimes, larger condos will offer amenities similar to a resort: multiple pools, gym, even an on-site restaurant and/or a spa. 

We do love a good luxurious 600+ thread-count-sheet-clad bed and room service so we don’t mind being pampered at a luxury resort for a few days. A split stay is great for a trip a week or longer! A few examples of this are:

  • Maui 2009 – 4 nights Maui Coast then 3 nights Ritz Carlton Kapalua
  • Maui 2010 – 3 nights Outrigger Aina Nalu then 3 nights Marriott Wailea
  • Oahu 2011 – 1 week in a Waikiki condo from ($85 a night!) then 2 nights at Disney’s Aulani in Ko Olina
  • Oahu 2013 – 1 week in the same Waikiki condo then 3 nights at the Turtle Bay Resort on the north shore
  • Maui 2013 – 4 nights at the Andaz Maui, and then 1 week at the Honua Kai condo resort

There are a few caveats to a split-stay: I would only do this if it is cost-effective. Some condos require minimum of a week’s stay and many involve cleaning fees too. So break it down to see how much it would cost on a daily basis. Also, some people might be annoyed at having to repack and check into a new hotel. I actually enjoy experiencing new lodgings and spaces so to me that is just part of the adventure.

the living-dining area of our 3-BR condo at the Hali’i Kai on the Big Island


Poolside at the Hali’i Kai on the Big Island, booked via VRBO. We got a 2 BR luxury townhouse for less than the price of a 4-star hotel.

Priceline can also offer excellent deals, but once again this requires some research and patience. This worked out for me during our 3-night stay at the Marriott Wailea in Maui in 2010. The cheapest room was going for $325 a night on their website. Via priceline, I got the same room for $100 a night. It took a few tries to get it, bidding over several days but it was a pretty sweet deal!

Poolside at the Marriott Wailea


convertible on maui

I have not experienced this myself but during peak seasons some visitors have been unlucky enough to have been told at the counter that there are no more rental cars available! So book a refundable rate early and then recheck up until your trip so that you at least have a backup.
Priceline: If I don’t get my car rental for free I usually use Priceline. Yes there are rules to bidding and it can take a few days to get your price, but in the end it’s worth it. Sometimes you cannot get a deal until close to your departure date so I would always have a backup plan that I can cancel just in case. Costco has some of the best prices for cars in Hawaii and the good news is that they are usually refundable. So I’d book and recheck all the time, the prices oftentimes go lower so you can cancel and re-book at the lower rate.
Discount Hawaii Car Rental: I have not used them yet but a lot of people recommend them – they are known to have great prices and a good cancellation policy.
Hotwire: once in a while Hotwire will come up with a great rate that I can’t pass up. They are not refundable but if the price is low and I don’t want to deal with Priceline bidding then Hotwire may be a good option.



View of Ala Moana beach park (oahu) from the air while flying to big island

Airfare is rather tricky because there are constantly fare sales and fare wars that can drive prices all over the place. I can’t really tell you WHEN and HOW FAR OUT to book your flights because they may change and even I would like to know when to book myself. If you happen to have any tips, please feel free to leave them in the comments!

I once purchased what I thought were “cheap” flights direct RT from NYC to Oahu on Hawaiian Airlines – plus I had a coupon which gave me an additional 25% off. I thought it was a great deal, until 2 months later when the flight prices dropped drastically. When combined with that coupon, I would have saved probably an additional 180 dollars per ticket. I called up Hawaiian air and asked about a price difference refund of any sort, and they didn’t really have one. They said the change fee would offset any of the cost difference, so I didn’t do it. However, they did offer me free checked bags for the both of us on the RT flight. (200 dollar savings) which is I guess more than adequate. Other airlines such as Alaska Air are a little better in terms of price changes and won’t charge a fee.

My best way to save on Airfare is to try and get your flights for free!

I’d find out what airlines fly to Hawaii from your nearest airport, sign up for their miles-earning programs/credit cards and do my best to boost my miles through everyday spending, and shopping through their portals where you can get 10x even 20x miles. I’m not a super expert on this but I try my best based on our budget. It’s a very lucrative business and there are a lot of bloggers/websites which explain this in more detail.

I flew Steve and I from Newark to Maui, then Kona back to JFK for 80k United miles total. I had some miles in my United account but it was all made possible by a 50k point signup bonus from my American Express Membership Rewards card – which I transferred into United Miles. Nowadays, United is no longer a partner to transfer miles to from American Express but Hawaiian Airlines is!

My particular airline favorites to Hawaii from New York are United and Hawaiian Air, mainly because they have the most availability, as well as having direct flights. JetBlue also partners with Hawaiian as well, so JetBlue is a good airline if you fly it a lot. If you live on the west coast, you will have even more options!

Also sign up for a bunch of travel newsletters. I like Travelzoo, as it gives me a heads up as to what fare sales are going on and I begin my research from there. One of my favorite sites is Beat of Hawaii which will notify users of any upcoming sales, and new airline routes to the islands.


I hope you find these tips helpful, they have surely saved us a bunch over the years! I find we’d rather go to Hawaii on a moderate budget more often than have an extravagant trip only every few years. Using these tips helped us travel to Hawaii more frequently, and stay longer – all while keeping a nice balance between budget and luxury. 

Check out my Cheap Eats Maui series!

October 16, 2013 - 12:38 am

Ellen - Wow-that’s a lot of work but so worth it. Great insider tips. Still waiting for hubby to take me to Hawaii one day!!!

October 16, 2013 - 12:51 am

Su-Lynn - Yeah it is a little bit of work but once you narrow your destinations you want to go then look at only airlines and hotels that have good points there, it shouldn’t be too bad. Yes! You guys should go. It’s so fun.

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