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.
Sunset at Grand Wailea
Open-Air Lobby
Lobby Bar with a beautiful ceiling
Famous wedding chapel at Grand Walea
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.
Terrace room with two queen beds are quite spacious, hotel would even put in a roll-away bed upon request.
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.
Activity table is ready for kids at Camp Grande.
Rides in the Fishpipe cost additional.
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.
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!
Conclusion
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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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
There is great Costco right at the exit to the airport. My plan has been to stop there to pick up snacks, sunscreen, drinks and other items before I head out to the resorts. There is also a good Safeway in Kihei for smaller amounts of perishables and at last Foodland for poke.
I haven’t been to GW in many years now. I was thinking about it but I hate the new room refresh. I really dislike the blah corporate same o same o room furniture.
Expensive parking and resort fees are the main reasons we skipped the Grand Wailea as well as Marriott Wailea Beach Resort and stayed at the Wailea Marriott Residence Inn where the room is also as spacious if not more, free breakfast, no resort fee, only $20/day for parking and no crowd.
Stay at the Grand Hyatt Kauai instead, especially when kids are traditionally in school. While the swimming complex is less extensive that at the Grand Wailea, they have 4 pools (including a TWO-ACRE saltwater pool with most parts that are 5 to 9 feet deep) and a water slide. They even have a Camp Hyatt for the little ones days and evenings. Trust me.
Just finished 4 nights at the GH Kauai and 2 free credit card nights at the Fairmont Kea Lani 3 resorts down. My advice – Take the short drive into Kihei for meals like we did. Grab sandwiches for lunch at the 808 Deli, and great local dinners at Antonio’s for fresh pasta or Café O’Lei. Yelp is your friend!