Grand Wailea Maui, A Waldorf Astoria Resort Review

Posted on March 22, 2020 by in HHonors, Hilton Honors, Hilton Hotels, Hotel Deals, Hotel Loyalty Programs, Hotel Reviews, Travel Deals, Travel News

The Grand Wailea Maui is the ‘Grande Dame’ of Wailea resorts that control the area south of Kihei on the island of Maui. While the area beaches are all publicly accessible by the way of the beautiful public beach walk – there is a never-ending line of resorts that open into the beautiful waters of Maui.


When we arrived the check-in area had long lines but just two attendants working the line slowly. There is a massive concierge and tour desk right across the lobby but at rates of $700++ who would like to wait for check-in for 30 minutes in a long (but orderly) line? Well, that seems to be the plan of the Grand Wailea. Check-in itself was quick and knowledgable with the attitude you get at high-end restaurants in San Francisco. The person checking us in made it feel they did us a favor to give us a room – indeed a big favor! Again there was nothing technically wrong with the check-in but it does not get much colder and less ‘Aloha’ Attitude than that.

In general, the resort looks enormous (it is!) and really old (it is!). It also looks really beautiful with perfectly manufactured gardens that open towards the even prettier beach. The Grand Wailea indeed has the best. spot along the coastline with a wonderful beach and clear water lagoon that rarely gets too much surf. No other can match this in Wailea. Also, next door is the Shops at Wailea and more strip malls offering a good amount of eateries, coffee shops, and shopping.


Our room looked much nicer than I expected. It was big with a huge bathroom that comes with a fantastic shower (a little low on the pressure though). It felt more like a rather new Intercontinental than a Hilton. It was great!


I wasn’t a fan of the bed – it was comically soft – I felt I disappeared into the mattress. I prefer (extremely) hard mattresses instead. There also was an odd space between the headboard and the bed itself which made it tough to find a comfortable position initially. My other pet peeve is slow (or unreliable Internet) – on day one the Internet was slow just under 10 Mbit which is ok for a Holiday Inn Express but I expected more with a 5 Star Hotel charging $700++. On day two it was much faster but also much more unreliable with connections breaking every 30 minutes.

The resort offers a complimentary (one plate) breakfast for Hilton Diamonds in the breakfast area. You do not get to choose any items from the buffet but are presented with a set plate. I found the options of very low quality – no Starbucks would get away with it (I’m not a fan of the Starbucks pastries at all).


I found most of the employees to be indifferent at best – oblivious at worst. Like many other Hiltons on Hawaii, the Grand Wailea is a ‘mass tourism machine’ and I can see how hard it is for employees to stay sane with the attitude many tourists show. Still, I find the high price tag should demand a better service.

The outdoor areas are clearly the main draw – the pool area is well done and avoids crowds by separating the area into many smaller pools that do not form huge bottlenecks.

I’m a big fan of the beach area right underneath for its clear water, beautiful sand bottom and lovely body surfing waves (at times). Keep in mind that it is accessible without charge for anyone. The Grand Wailea. provides beach towels and a sun bed and umbrella free of charges for hotel guests (as long as there is capacity). Boogie boards and snorkel gears can be rented right there but aren’t cheap at $20 a day (for a boogie board for instance).

In sum the Grand Wailea shares many characteristics with the Hilton Hawaiian Village Waikiki Beach Resort (Review) and the Hilton Waikoloa Village, Big Island resort. It has a beautiful location, great outdoor areas along the beach and decent rooms. However, the lacking staff attitude, the long lines, the unappealing food and the general feeling of crowds make it more ‘downmarket’. I’d come back for $200 a night but felt the $700 room rate provided no value at all.

About the author: Torsten is a serial entrepreneur who started almost a dozen ventures on four continents. Torsten's love for travel has brought him to 130+ countries and travel with most of the world's airlines. You can reach Torsten at [email protected]

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