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My family’s two-week Hawaii vacation this month started with three-night stay at the famous Grand Wailea, a Waldorf Astoria resort located in Wailea area of Maui. This wasn’t our first visit to the resort, but it was the first time me here as a Hilton Diamond member. Just like prior visits, my feeling about the resort is mixed between love and hate.

Grand Wailea is absolutely gorgeous

There is no doubt that Grand Wailea is a beautiful resort, from the lobby, to the grounds, the pools and the beach! I will let the pictures speak for themselves.

a water fountain in a park with palm trees and a gazebo

Sunset at Grand Wailea

a large room with a large chandelier and a large table

Open-Air Lobby

a large building with a fountain

Lobby Bar with a beautiful ceiling

a building with a garden and palm trees

Famous wedding chapel at Grand Walea

a beach with palm trees and umbrellas

Stunning beach

Check-in was a breeze

We arrived at the resort around 3pm, just a little before check-in time. I didn’t see any separate check-in line Hilton Elite members, but luckily there was only one person ahead of me so the wait wasn’t long. Noting that I was Hilton Diamond member, the nice lady at front desk apologized that they were unable to upgrade my standard room because the hotel was sold out. But she offered the four of us free buffet breakfast for the entire stay. Resort fee was waived because my room was booked using 80,000 Hilton points per night.

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Nice remodeled rooms

We were given a room on the 8th floor in the Molokini Wing, which was quite a hike from the lobby. We had to pass all the shops and Café Kula before reaching the elevator. The room had been remodeled since our last visit. It was quite spacious with two queen-size beds, a desk with two chairs, a 6-drawer dresser with a giant TV above. The bathroom had only one sink, a private toilet area, a separate shower and bathtub. Our room faced the parking lot and the hotel next door, but it did have a nice view of the hills as well.

a woman sitting in a chair in front of a television

Terrace room with two queen beds are quite spacious, hotel would even put in a roll-away bed upon request.

a balcony with a view of palm trees and a city

Our balcony has a nice view of the rolling hills, even though it overlooks the parking lot and the hotel next door.

Crowded family friendly resort

Grand Wailea is a very family friendly resort, with several pools, slides, lazy river, water elevator, and many  watersports keeping kids and adults entertained. The downside of course, the resort is really crowded. Chairs are stacked against each other in both the pool and lawn area to accommodate the crowds.

a table with white tables and white umbrellas

Activity table is ready for kids at Camp Grande.

a large inflatable ball in front of a fence

Rides in the Fishpipe cost additional.

a group of people in a pool

Crowds awaiting for the water elevator!

Everything is expensive here

I really hate how everything is so expensive here in Grand Wailea: valet parking is $30 a day; resort fee is another $30 a day; bottled water is $3 each, a bag of popcorn is $6, breakfast buffet $35 for age 12 and older, and so on. Café Kula probably has the cheapest price for all three meals a day, but you get bored with it quickly. Our dinner at Bistro Molokini was $120 for four people including tips, and we didn’t even order dessert or drinks! We had dinner one night at Humuhumunukunukuapuaa and it was super expensive. Yes we did venture out of the resort to eat, it didn’t really save that much money since the entire Wailea area is just expensive.

a building with a thatched roof over water

The famous restaurant at Grand Wailea – Humuhumunukunukuapuaa

Somehow in the three nights we stayed, we racked up enough charges to take advantage of the Amex Offer for $200 statement credit for Hilton Hawaii properties. I guess any form of savings helps!


Yes I do love the Grand Wailea. It is beautiful here. But I also hate how crowded it gets and how expensive everything is here. Will I come back again? I am not sure, but I do like the Wailea area more than the other parts of the island. If you have tips on how to save at Grand Wailea, I would love to hear.


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