Grand Wailea vs Four Seasons

The Grand Wailea and Four Seasons hotels are two of the finest establishments on all of Maui.

It’s also no coincidence that they’re located less than half a mile from each other, in the Wailea region of Maui. This is one of the hottest areas for tourism, with a variety of hotels and resorts competing for you to stay with them.

In this comparison review, we’ll be taking a close look at the vacation experience the Grand Wailea and Four Seasons hotels can provide for your stay.

Beach at sunset on Maui.


There isn’t much difference between the Grand Wailea and Four Seasons in terms of their location, except for a couple of key features in the surrounding areas.

The Grand Wailea is located slightly closer to the Wailea Blue Golf Course. If golf is something you’re interested in, it’ll be a lot easier to travel with a set of clubs from the Grand Wailea.

On the other hand, the Four Seasons is a little closer to the Wailea Point Village, allowing better access to local stores, cafes and restaurants.

But, in general, neither of these locations is necessarily better than the other, it’s simply a case of deciding which is better for you, based on what kind of vacation you want to experience.

Rooms and Suites

Having a comfortable place to relax and sleep at night can make or break a vacation. That’s why it’s important to decide which hotel has the best options available, before booking.

The Grand Wailea

The Grand Wailea has a great variety of suites, all decorated with unique style, meaning no two suites look the same.

Most of the suites at the Grand Wailea sleep a decent number of people, with options for a variety of party sizes.  Many of them have their own separate bedroom and living areas, giving you plenty of space to relax in privacy.

Some of the high-end suites even come with their own luxury kitchen and garage, making it feel more like a home than a hotel.

Even the more basic guest rooms feature gorgeous views of the ocean, garden or mountains. The best aspect of the Grand’s accommodation options is that there’s a variety of sizes and prices available, but all their rooms and suites are very well equipped and decorated.

Four Seasons

At the Four Seasons, we find a similar story. A very healthy range of rooms and suites are available, with different sizes of each depending on your party size. The Four Seasons also provides options for ocean, garden or mountain views.

The suites at the Four Seasons also feature all of the same amenities with certain accommodation types as the Grand, making it very difficult to split the two.

The only significant difference between the hotel accommodations is that the Four Seasons doesn’t provide any options with a kitchen or garage, encouraging you to visit their restaurants instead.

While almost all of the accommodation options at the Grand and the Four Seasons are just as good as each other, the high-end suites at the Grand provide a slight edge over the competition.

Four Seasons outside areas in Maui.


Enjoying delicious food and drink is probably one of the best parts of any vacation and both the Grand Wailea and Four Seasons have plenty of options to keep you well fed.

The Grand Wailea

At the Grand, a variety of food options are available in their on-site restaurants or as room service.

With everything from seafood and steak from the colorfully named, Humuhumunukunukuapua’a, to tacos and poke bowls at the Aloha Trick Pony Food Truck, it’s unlikely that you’ll ever run out of food and drink options at the Grand.

The Grand Wailea also provides some exciting dinner side entertainment in the form of their weekly luau, making meal times even more enjoyable.

Four Seasons

At the Four Seasons, a similarly diverse range of food options are also available at a great variety of locations.

The Four Seasons boasts the only oceanfront restaurant in Wailea with Ferrero’s Italian Bar e Ristorante. Similarly, the Californian and Hawaiian fusion restaurant, Spago, features legendary chef, Wolfgang Puck’s exquisite menu.

As well as the wonderfully classy dining experiences available from the Four Season’s restaurants, they also provide plenty of options for room service and more casual beachside cafes.

Overall, it’s pretty tough to decide which of the Grand Wailea or Four Seasons provides the best dining options but we have to give it to the Four Seasons.

It’s clear that they’ve invested heavily in providing the highest quality food you can get on the island.

While they don’t have the benefit of dinner side entertainment like the Grand does, the immense quality and choice of cuisine puts the Four Seasons out in front for this category.


Both the Grand Wailea and Four Seasons offer their guests plenty of things to do during their stay.

We’ve already mentioned the dinner side weekly luau at the Grand but they also provide cultural tours of the area and activities that will immerse you in Hawaiian culture.

The Grand’s other activities include beach yoga, garden tours, Maui adventures (including whale watching) and scuba diving. If that isn’t enough to keep you entertained, they have a spa, fitness center, and swimming pools.

Over at the Four Seasons, it’s a similar story. They provide complementary daily activities including a putting green, croquet lawn, games room, and many more. The hotel has a top class spa and fitness center, and even has its own salon and barber.

There certainly is a lot to do at both hotels, so you’ll never be bored wherever you go. However, we think the edge goes slightly to the Grand Wailea.


Whether you choose to stay at the Grand Wailea or the Four Seasons, we can guarantee it’ll be a vacation that you’ll remember for a lifetime.

Here’s the final breakdown of the best hotel in each category:

  • Best location: Both
  • Best accommodation: Grand Wailea
  • Best dining: Four Seasons
  • Best activities: Grand Wailea
  • Best overall: Grand Wailea (though it is a very close contest!)
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