Top 5 splurge-worthy stays in Hawaii

Estimated reading time: 2 minutes


Finding the Aloha State's most heavenly hotels

Sometimes it’s fun to splurge on a trip (like, really go for it for a moment, a night, or a week). I’ve done this a few times in the name of investing in experiences over things.

To maximize my travel budget and end my vacations on a high note, I often check-in at a posh property for the last few nights of a getaway. Hawaii is my go-to destination to add a few extra stars to my stays, given its sure-thing weather, palm tree perfection, rock star-status hotels, and legacy of curated escape.

With this I give you the splurge-worthy, 5-star life, Aloha edition.

oceanfront bungalow mauna lani bay hotel + bunglaows

THE ISLAND OF HAWAII: Mauna Lani Bay Hotel & Bungalows

Without naming names, let’s just say that a number of travelers—the types who have private jets—touch down at Mauna Lani Bay Hotel & Bungalows regularly. While the hotel has numerous rooms and suites fit for fabulous frequent fliers, the Bungalows provide that extra dose of wow-factor with their 2,700-square-feet of living space sprawled across two bedrooms, two master baths (complete with TOTO Toilets, and rain showers cascading into a tropical garden), a kitchen, and a wet bar. Couple this with a private pool and jacuzzi, and sunset views over the Pacific, and you may want to move in (or become BFFs with a private jet owner).


MAUI: Four Seasons Resort Maui at Wailea

As a regular stop on celebs’ travel itineraries, the Four Seasons Resort Maui at Wailea is a staple stay for those who like the finer things in life: haute-couture art, chic poolside treats, customizable beds, and the option to “posh” your drinks (insider tip: Add bubbles to put some sparkle in your “spirit”), and suites with a personal assistant. In a meticulously planned move, the property just “poshed” itself transforming everything from the presidential suites to the pool cabanas making it an even more exclusive place to see, be seen, and be unseen on the Wailea coastline.   

four seasons resort lanai at manele bay

LANAI: Four Seasons Resort Lanai

Don’t walk, fellow luxury lovers, RUN to the Four Seasons Resort Lanai, an off-the-beaten-path hideaway catering to those who want to explore Hawaii’s private island paradise in style (spoiler alert: It’s only a 35-minute ferry from Maui). Like its luxe sibling in Maui, this  Four Seasons also underwent a recent multimillion dollar renovation upgrading every fit and finish to it-status. Case in point: their pool is actually a lagoon, their room keys are actually waterproof wearables (so you don’t lose your key while playing in the waves), and their restaurant, NOBU LANAI, is actually the world’s only NOBU to source greens from its own on-site garden.

halekulani oahu

OAHU: Halekulani

As one of the Aloha State’s most sought-after stays since 1907, this Waikiki legend offers a throwback to the warm and welcoming hospitality that has made the tropical paradise famous (in addition to the gorgeous beaches, that is). Inside the 453-room hotel, Halekulani‘s rooms are beautifully decorated with plush white-on-white textures to highlight the technicolor shoreline meeting each guest’s gaze. At the cusp of this coastline, don’t miss House Without A Key, the hotel’s outdoor restaurant preserving a time-honored tradition: cocktails, live music, and hula under their century-old Kiawe tree. Visit at the day’s end to drink in one of Hawaii’s most dreamy scenes with a Mai Tai in-hand.

koa kea hotel & resort

KAUAI: Ko`a Kea Hotel & Resort

With 121 rooms, this boutique-style hotel recalls retro Hawaii with its tiki architecture and modern Hawaii with its upscale amenities (think: In-room Nespresso). Located on the sunny South shore of the Garden Isle, Ko`a Kea Hotel & Resort is the island’s closest hotel to the ocean, and ups its own ante brining the surf to turf with its saltwater pool. Since breakfast is the most important meal of the day, beeline for the hotel’s Red Salt restaurant to nosh on local favorites: macadamia nut- and banana-topped topped Belgian waffles and lemon-pineapple soufflé pancakes to get some Vitamin T (tropical) before you even hit the beach!

Viewfinder Tip: Get smart about splurging on hotels in Hawaii. Many of these resorts offer fourth-night-free promotions in shoulder season.

What stay in Hawaii would prompt you to spend a little extra?

Want more Hawaii inspiration? Check out Expedia’s Discover Your Aloha page and create a personalized itinerary of Hawaiian experiences.

[All photos courtesy of hotels mentioned. Lead photo of Mauna Lani Bay Hotel & Bungalows’ pool]

Expedia compensates authors for their writings appearing on this site, such compensation may include travel and other costs.

This author has either a relationship with, or received other compensation (which may include monetary or in-kind compensation) from, the product or service providers that are the subject of this post.

Trip Styler

Trish Friesen chose an unlikely profession given her fear of flying and propensity toward car, air, boat, train, and chairlift sickness. Thanks to Gravol, Sea-Bands, and cruise ship stabilizers, the reluctant—yet enthusiastic—jetsetter packs her bag once every two weeks to swim with sharks in the Great Barrier Reef or to sample the latest libation in Portland. Trish unpacks her suitcase in Vancouver, Canada, Eh! where she’s the editor-in-chief of, a travel lifestyle website for aspiring jetsetters. Find her moonlighting on Expedia, Fodor's, Jetsetter, and as a travel expert on TV while circumventing the globe with her entourage: a MacBook Air, an Olympus camera, and the biggest carry-on she can fit on the plane.

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