So you want to come to the island and experience the best of Maui. AWESOME.  Every traveler is different and has different tastes.  Hawaii has many options for you, and here are the insights.


I’ve seen many travelers request an all-inclusive resort recommendation. In short, they don’t exist on the islands at all.  If you want to be pampered and stay on the resort, just expect that you’re going to have to pay for your lodging and your food and entertainment separately.


Maui has some incredible (and I truly mean incredible) hotels to stay at.  You’ll want to think of the area you want to be in, what you want proximity to, and the amenities that matter to you.  You’ll find budgets will begin around $300 per night and go up sharply from there.  Lots of travelers request a hotel/resort that’s walkable.  That’s really not a thing on Maui, but there are a few exceptions in Ka’anapali.  Plan to drive short distances to get where you want to go… and believe me, you’ll appreciate your freedom.

As for my recommendation, The Grand Wailea has the island’s best pool and one of the best you’ll find anywhere. It’s great for kids, adults, and full relaxation.  Some of the rooms are a little tired, but you’re not there to be in your room.  The spa is famous around the island and elsewhere, and for good reason.  This resort is a bit expensive, but if you plan to be at the resort to truly unwind, it’s a good investment.

  • South Maui (Kihei/Wailea) has a very cool, low-key neighborhood vibe once you leave the resort, with lots of small businesses you’ll fall in love with.  Very sunny, amazing weather almost every single day.  Wailea is very elegant and is home to five large resorts, including the Four Seasons.  Shops in proximity.
  • Sugar Beach (Ma’alaea) is very beachy, and you’ll find some good options at lesser prices than other parts of the island. Very high wind, lots of sunshine, but not as much as South Maui.  Great for whale watching from your room.  You’ll need to drive 10-15 minutes to get to things in South Maui, but there are a few things to do in that area.
  • Ka’anapali/Nipili has an upscale vibe catering to visitors. Teeming with things to do, great snorkeling at Black Rock beach 80% of the time, and beautiful beaches, it’s popular for a reason.  This area is elegant like Wailea, but has a more resort-tourist vibe.  Shops in proximity.


There are lower priced options for visiting the island, including a Days Inn. They are harder to find on a Google search (the resorts with all the money to pay for advanced search engine optimization come up first), and my advice to you regarding motels is to pull up Google Maps (or click here) and search that way.


For me, the ultimate luxury is getting to have my cake and eat it too.  I like to spend my time away from my lodging, and spend my money in the small businesses in the area.  I like a pool, and I like comfortable amenities.  What’s great about this option is that you get a home away from home, with a kitchen.  For me, I do not like eating breakfast out.  Ever.  I like to do things that AirBnb’s and VRBO’s offer: make my breakfast, wash my clothes, visit the beach with chairs/towels/toys/umbrellas/etc. and feel like I’m at home.  And not pay a fortune for it.  I get to visit where I’m going more and longer and stretch my dollars.

That said, get the app you prefer and search by area and amenities.  Here are the amenities I can’t live without:

  • Pool
  • Hot tub
  • Kitchen
  • Laundry
  • Air Conditioning
  • Free Parking
  • 1 bedroom (not just a bed)
  • View

Many places include beach things like chairs, etc… and that alone saves you $$.  Wealth is not about how much you have, it’s about how much you keep.  For me, I like to live well, and keep as much money as possible for myself and for the things I care about (like supporting small businesses).