I’ve been a Hilton superfan for years (proud Diamond member here!), and I can confidently say that the Grand Wailea, A Waldorf Astoria Resort, is my all-time favorite. Perched on Maui’s stunning Grand Wailea shores, this resort perfectly blends luxury, relaxation, and adventure. Even Paris Hilton herself has been going here as part of a family tradition since she was a young girl (fun fact: we even met her during our last visit)! Adam Sandler was there as well but we unfortunately did not see him. His movie with Jennifer Aniston, Just Go with It, was actually filmed at the Grand Wailea.
Don’t let the high room rates scare you off—there’s a way to experience this incredible resort without paying full price (or even a resort fee). I’ll share exactly how I made it work, along with everything you need to know about what makes the Grand Wailea so special, below.
Using Hilton Honors Points for the Grand Wailea
One of the highlights of my trips to the Grand Wailea is that I’ve been able to book my stays using Hilton Honors points. The ability to redeem points for a stay here is a testament to the value of the Hilton Honors program, allowing travelers to indulge in a world-class resort without breaking the bank. Not to mention you don't have to pay a resort fee when you book on points. I redeemed 110,000 points per night on a Garden Room view which was very spacious, had a spa-like atmosphere, and pretty good views no matter where you are in the resort. I've stayed here twice on points with my spouse. First Garden View room we had was a few floors up overlooking the chapel and ocean, and this year we had a room on the ground floor that walked out straight to the pool. Both rooms lived up to the hype for us. I was able to build up points for this by using my Hilton Honors American Express Surpass® Card which allows me to accrue points on groceries, gas, restaurants, etc. You get even more points when you use it on any type of Hilton spend.
Restaurants & Bars
The resort has a variety of bars and restaurants, offering everything from casual bites to fine dining experiences. You can eat and sip cocktails at the iconic Grotto Bar (bartenders Wayne and Tim are amazing), or enjoy a sunset dinner at one of the restaurants surrounded by water. We always ended our night at the Botero Lounge in the lobby area (which has an open roof) and Keoni was just simply the best bartender.
While the on-property options are incredible, those traveling on a budget will be pleased to know that there are fantastic dining alternatives just outside the resort. Hawai'i is pretty expensive in general compared to where I live, but it's good to know Maui’s local food scene offers plenty of opportunities to enjoy fresh, delicious meals without splurging. The Pint & Cork and Monkeypod Kitchen are two great options and are walkable from the resort. You can also check out nearby resorts and the shopping area down the street for more choices.
A Beach Lover’s Paradise
The Grand Wailea’s beachfront location is one of its most stunning features. The pristine sand and crystal-clear waters are perfect for relaxing or enjoying activities like snorkeling. We did a lot of snorkeling here and saw a few turtles and fish, particularly by the rocks. You can rent snorkeling equipment for $25 at the resort or purchase your own set at a local store. We opted for the latter so we could go snorkeling again elsewhere.
You can also walk along the sidewalk between the resort and the beach to see different areas of Grand Wailea as well as other resorts. A few spots offer good views of whales breaching and turtles swimming, especially in the early morning hours. Plus, a sunrise here is just so peaceful to watch.
Beautiful Pools & Poolside Dining
The resort’s pools are nothing short of spectacular. With options ranging from family-friendly pools with water slides to a serene adult-only pool, there’s something for everyone (view all options here). There are a few hot tubs as well in the adult-only area and outside the Grotto Bar (which is like a cave, which is really cool). It’s easy to spend an entire day enjoying the sun and water without feeling the need to leave the property. I learned that the poolside menus for food and drinks are different from those at the Surf Haus (which is by the pool), which is worth noting if you see something one day and are looking for it the next!
Rejuvenate at the Kilolani Spa
The Grand Wailea’s recently renovated Kilolani Spa elevates your relaxation level even more at this resort. Whether you’re indulging in a massage, facial, or one of their signature treatments, the spa provides a tranquil escape from the hustle and bustle of daily life. My husband opted for the hyrotherapy two-hour pass for $125 and said it left him feeling like a new person between the ice baths, sauna, steam room, and more. I need to embrace the spa more next time I go!
Conclusion
The Grand Wailea, A Waldorf Astoria Resort truly embodies the best of what Hilton has to offer. From its luxurious accommodations to its stunning location and endless amenities, it’s no wonder it’s my favorite Hilton property. And with Paris Hilton herself endorsing it as one of the best, you know it’s worth the visit! I've shared more pictures below for you to explore. Whether you’re redeeming points or splurging on a dream vacation, the Grand Wailea promises an unforgettable experience. If interested, you can view more of my favorite Hilton hotels and resorts by clicking here.
Looking for a travel guide of all the things to do in Maui? Check out my list on Benable.
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While I have Hilton membership I have not spent enough time to reach any kind of meaningful status level. But the Grand Wailea sure looks like a lovely spot to enjoy as a Diamond member. We stayed at the other end of Maui when we visited. So this would give us a very different experience.
This Hilton property looks amazing! I'm more of a Marriott girl myself, but I have like 100,000+ hilton points saved up. Using points to stay at pricey properties is definitely the way to go!
My husband and I have stayed at some awesome Hilton resorts. This is another one to add to our list.
Sunrise on the beach looks stunning. That would be a perfect place for yoga.
Looks like a great place to stay! Love Waldorf Astoria NYC