Award Yourself A Hawaiian Vacation

Award Yourself A Hawaiian Vacation–The Best Award Stays In Hawaii   

Hawaii will always hold a special place in my heart. I fell in love with Hawaii on my first trip to Maui in 2002. We were greeted with leis and I learned how to properly carve and serve a pineapple. By the way, you will never taste a sweeter pineapple than a real Hawaiian pineapple.

Both my then boyfriend and I loved Maui so much that, when we got engaged there was no doubt in our minds about where we wanted to get married and spend our honeymoon. We were married in a sunset ceremony on a tiny beach near Wailea, one of the most beautiful areas of Maui.

With Southwest announcing its plans to begin flights to Hawaii, now is the perfect time to start planning another trip to paradise. You can use your companion pass for two for one flight to Hawaii and there are many ways to use points for free hotel stays.

There are so many options in Hawaii, from the grand dames like Grand Wailea, Hilton Waikoloa Village, and Fairmount Kea Lani. Or, more off-the-beaten-path accommodations in places like Hana. There are options for great redemptions using hotel points for all the big chains, and you can spend as little as 12,000 points a night or as much as 80,000 points.

First, decide what is most important to you in a hotel redemption. For me personally, location is the main deciding factor. When I'm visiting an island paradise like Hawaii it’s all about the beach! I want to stay by the ocean and I'm willing to spend more points to be right on the beach.

Related: How To Fly To Hawaii For Free Using Travel Rewards

You'll get the best bang for your buck (or points, in our case) by staying at a lower tier hotel, such as Hyatt Place Waikiki Beach for 12,000 pts/night. You can also use Chase Ultimate Rewards portal to book a non-chain hotel pretty much anywhere on the islands.

Let’s look at some of the best point values and best redemption options for hotels in Hawaii.


  • Hyatt Regency Maui Resort and Spa–20,000 pts/ night
  • Marriott’s Maui Ocean Club–Molokai or Maui & Lanai Towers, Marriott’s Maui Ocean Club–40,000 Marriott pts/night or 14,000 SPG pts/night


  • Grand Hyatt Kauai Resort and Spa 25,000 pts/night
  • Sheraton Kauai Resort 12,000 SPG pts/night
  • Koloa Landing, Autograph Collection 40,000 Marriott or 14,000 SPG pts/night
  • Wyndham Koloa Landing at Poipu Beach Wyndham Grand Resort 15,000 pts/night
  • Hilton Garden Inn Kauai Wailua Bay 30,000–40,000 HHonors pts/night


  • Hyatt Centric Waikiki Beach–20,000 pts/night
  • Hyatt Regency Waikiki Beach Resort and Spa–20,000 pts/night
  • Hyatt Place Waikiki Beach–12,000 pts/night
  • Waikiki Beach Marriott Resort & Spa 40,000 Marriott pts/night or about 13,400 SPG pts/night
  • Courtyard Waikiki Beach 35,000 Marriott pts/night or about 12,000 SPG pts/night
  • Sheraton Princess Kaiulani 12,000 SPG pts/night or 36,000 Marriott pts/night
  • Hampton Inn & Suites Oahu/Kapolei 40,000 HHonors pts/night
  • Hilton Hawaiian Village Waikiki Beach Resort 60,000 HHonors pts/night

Big Island

  • Sheraton Kona Resort & Spa At Keauhou Bay 10,000 SPG pts/night
  • Hapuna Beach Resort 12,000 SPG pts/night
  • Hilton Waikoloa Village (select rooms) 50,000 HHonors pts/night
  • So as you can see there are many options for a great Hawaiian getaway without breaking your points bank. You can maximize your hotel points by taking advantage of stay four nights get 5th night free perk. Both Marriott and SPG have this option and Hilton offers this perk to their elite members.

Flexible currencies, non-chain hotels, and condos

I'm personally a big fan of flexible currencies such as Chase Ultimate Rewards points. Chase has a few cards that earn Ultimate Rewards points. The most popular are Chase Sapphire Preferred, Chase Sapphire Reserve and Ink Preferred.

You can use Ultimate Rewards points to book many non-chain hotels and vacation rentals in Hawaii (including on the beach!). You can also transfer Ultimate Rewards points to many hotel partner programs. If you have Chase Sapphire Reserve and you are using Chase travel portal, your points are worth 1.5c/point. If you have Chase Sapphire Preferred, Chase Ink+ or Chase Ink Preferred the points are worth 1.25c/point. The price in points will directly correlate to the dollar price of the hotel, so your redemptions will vary depending on the time of the year and the type of property you choose.

Click Here to get more details on this card and compare to other travel rewards cards!

This might be a good option if you like to stay in condos, non-chain hotels or a bit off the beaten track. For example, you can book Travaasa Hana hotel in Hana, Maui for about 70,000 Ultimate Rewards pts/night. Not cheap, but if you have your heart set on staying at a one of a kind luxury property in an amazing setting like the town of Hana there aren’t a lot of other options.

You can also use cards like Capital One Venture or Barclaycard Arrival Plus to “erase” your travel purchases. Check with your credit card what they code as travel and book your accommodations. Just book and pay for the hotel like you normally would then log into your online account and “erase” the charge with your miles.

Tell us about your great Hawaii redemptions. Where you stayed, what points you used and how you optimized your Hawaiian vacation.

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10 thoughts on “Award Yourself A Hawaiian Vacation–The Best Award Stays In Hawaii   ”

  1. This is really cool. Thanks for this write-up. I hadn’t heard of Southwest’s big plans. Looks like Hawaii 2019 here we come.

    Did you find these hotels via or maybe from some other source we should all learn about? With my typical skepticism, I did cross check a few of them with Awardmapper and even followed through to verify the actual lodging sites confirmed that data and sure enough you really can do Hawaii quite reasonably.

    • I like a dose of healthy skepticism myself :). Awardmapper is a great tool. Sometimes I think first about where I am going and then look at hotel options and sometimes I see that there’s a great redemption opportunity and build my itinerary around it. Chase Travel portal doesn’t have all hotels options but they have enough and it might sense to use your UR points to book your accommodations. Keep in mind, if you are going during peak season hotels might run out of “standard” rooms so you either will have to spend more points or won’t be able to book at all so always book well ahead of time for Christmas, Spring break etc. if you can.

      Rumors are SW will start flying in a few months from CA first. Hopefully they’ll add more flights soon!

  2. Great article! I am glad to learn I could use Chase UR to book accommodations in Hawaii. I am not planning on going there this coming year, but it is definitely on the bucket list.

  3. I just used British Airways miles on Alaska Airlines for the flights from San Diego to Kona 25k mi.+$11 each, book by phone. Then my husband and I both got the SPG cards and the signup bonus covered two nights at Westin Hapuna Beach and 5 nights at Sheraton Kona. Now we are 2 mos away, so I will get the Cap1 Venture card to erase the car rental, which was booked with AutoSlash. Easy peasy free vacation!

  4. Hi ChooseFI,
    Thanks for the wonderful podcast because it encourage and motivate me to save in hoping to retire the next 10 years if I reach my number. Do you have any tip for booking a Disney cruise. My family is planning to go next summer.
    Thanks for all your guiding light.

    • If you have one of the Chase cards check Chase Ultimate Rewards travel portal for cruises. You might want to call them to see if they have Disney cruises too.

  5. Hi
    We have accumulated alot of points with several cards over the past year. I am on the east coast trying to book a trip to Hawaii. I tried going to delta to find a flight like you described. I don’t see anything called a “level 1 saver flight.” The cheapest flight is 180,000. Are there certain dates or locations I need to fly from on the west coast? Does the miles change when I call Korean air?

    • Cheri,

      The biggest challenge with Delta is finding saver level award space. Delta eliminated their award chart and now displays fares according to supply/demand. If you see 180K flight, that means there’s no saver level awards. In order to book through Korean Air, a saver level award should be available. Are your dates flexible? What kinds of points do you have? Check out awardhacker website to see what other options you have and post your question in the group, you’ll get a lot of responses with people sharing their experience. Feel free to tag me too.

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