Get Set Hawai`i

Where To Stay – Hawai’i

One of my friends is headed to a wedding on Maui next month. He is looking for a place to stay that has location, charm, and an affordable price point.

Resorts & Hotels

If resorts are your thing, or if you win a raffle or contest—Kellyn, talking to you!—then relax and indulge. Places like Groupon Getaways, Hotwire, and TravelZoo offer cut-rate prices, especially on trip packages. Groupon Getaways is better for those who plan far in advance since dates are limited, while TravelZoo has both future planning and last minute options.

Hotwire is my favorite for last, last minute bookings (i.e. spontaneous weekend getaway where you’re booking things en route) and car rentals. Hotwire also has a mystery feature called Hot Rate Hotels where you can book 4 and 5 star places far below their typical price point. In this mode, you can review the general location (outlined on a map), amenities, see how others recommend it, and get a sense of the ‘class’ of hotel, but you cannot review actual pictures, the address, or the exact name. You are sent those specific hotel details as soon as you complete your booking. It’s a fun surprise box style of booking – I use it most for ski weekends or for good deals on airport hotels for one night layovers. is also a personal favorite since you earn a free night for every ten stays (the value of the free night is the average of the other ten) and they usually have the lowest posted prices along with sites like

In Hawai’i in particular, the Four Seasons is my favorite resort on Maui (in Wailea). On Oahu, I’d recommend The Royal Hawaiian Hotel (centrally located in ‘town’ aka Honolulu), Turtle Bay (north shore), and Ko Olina (leeward side which means the most reliable sun on the island; perfect for families or those who are afraid of the ocean, with their peaceful waveless and sharkless lagoons). On Kauai, I don’t think you can go wrong with any of the north shore, beachfront options.

Remember that if you want a daytime dash of the resort experience – i.e. mai tais out of a pineapple at a lush pool, beachy boutiques in a luxe setting, and amazing food – go for the day. Most resorts let you come in sans resort fee if you’re shopping and/or eating, and will often validate your valet parking as well.


Sipping a Mai Tai at the Maui Four Seasons.

AirBnB or VRBO

In Hawai’i, regardless of the island, I absolutely recommend staying in an AirBnB or VRBO rental. The best places and beach towns do not have hotels. Think Paia on Maui, Kailua or Haleiwa on Oahu, Hanalei on Kauai, and so on.

AirBnB or VRBO will not only give you prime location and walkability to beaches, shops, and food, you will also get a much more immersive, local experience and likely a much lower price point. I have rented various places in Kailua on my annual trips back (lived there when I did Teach for America) and every time I have had pools or beach access, clean and comfortable accommodation, and even a backyard pet tortoise once (Franklin, see below).

Want tips on how to select the perfect AirBnB or VRBO? Check out How To Pick Your AirBnB right here.


Franklin, our backyard turtle pet for the week, in Kailua.


Some beach yoga on Kailua Beach in Acacia swimwear.


View looking up from the backyard

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