It's near blasphemy to say, but for our money the 450-room Kea Lani outranks the neighboring Four Seasons as the loveliest resort on the island. Sure, boldface names flock to its more stylish, more lavish next-door neighbor, but to us the Fairmont feels friendlier and less pretentious—a more grown-up sort of luxury. There are no bad rooms among the 413 spacious, feng shui–styled suites. Some have panoramic ocean views and all have balconies. And if you want to splurge, the 37 two- and three-bedroom oceanfront villas (upward of $3,200 a night in high season, including rental car) will feel like your own private beach house. Your villa's stark-white Mediterranean-style architecture may seem out of place at first, but you'll have no complaints about the private courtyard plunge pool, great service, or palm-shaded setting. Villas also include an outdoor grill and full kitchen, but since KO restaurant—which serves a menu culled from the food traditions of Hawaii's plantation workers—significantly upgraded the Kea Lani's dining options, you'll be less likely to fire up the grill yourself.

The Four Seasons Maui is like a second home for the celebrity A-list crowd (Maui is an easy hop from L.A.). Perhaps inspired by the rave reviews of its sister properties on Lanai, the Wailea resort received a $50 million face-lift in 2007 that replaced the luxurious but grandmotherly decor in the 370 rooms and freshened the public spaces. The updated guest rooms combine the best of traditional Four Seasons—European luxury bedding and spacious marble baths—with energizing textiles in the reds, blues, and greens of the Hawaiian landscape. The idea was to create more harmony between the stunning beach views (available in 80 percent of the rooms) and the inner sanctum, now with HDTV and wireless. Of course, the pool area—with its cutthroat jockeying for first-come, first-served cabanas—is even more of a see-and-be-seen spot, with new plush lounge beds and towels. Spago is still fun for cocktails, but there's also the newer Duo restaurant, which serves a combo of aged steaks and fresh local seafood. And while the spa is less renowned than the one at the Waldorf-Astoria Grand Wailea next door, we think it's the best in Wailea because of the quality and diversity of treatments. The quality of service was never in question, yet that's improved as well. When you are a guest here, this is definitely a place where everybody on staff knows who you are.

Hana's lush beauty has been protected from overdevelopment by the daunting two-hour drive in or out on the twisty Hana Highway, and aficionados swear it's the last authentic place on Maui. This sprawling luxury ranch takes full advantage of the unspoiled setting: The eight one- and two-bedroom oceanfront Sea Ranch Cottages sit out where the land suddenly drops into the sea. The wooden houses have high, beamed ceilings, an enclosed garden off the modern bathroom, and interiors done up in vintage Hawaiian designs. There are amenities for guests at nearby Hamoa Beach, a pool that overlooks the ocean, and a state-of-the-art spa with open-air treatment rooms. An additional four Maui Bay Cottages sit closer to the main building, with views over Hana Bay or the garden, and for complete privacy, the turn-of-the-century Plantation House has two bedrooms and is a 10-minute walk from the hotel's main building (there's a shuttle service too). Attention, honeymooners: September is an adult-only month.

Everyone knows about Mama's Fish House restaurant in funky Paia. Now, these ten idyllic cottages nestled in a coconut grove in Kuau Cove, a small stretch of north shore beach, have also become too popular for their own good. Families and pairs of couples should book one of the four two-bedroom units, which each have a full kitchen for $475 per night—a much cheaper option than staying on Maui's west coast. If you can reserve one, that is. (Book as far in advance as possible; Mama's has been referring guests to the nearby Paia Inn because they are always sold out.) Staying here means that you can get takeout from Mama's restaurant and are a stone's throw away from adorable Paia Town. But the best perk is that there's not a resort in sight—just unobstructed views of the most magnificent windsurfing and surfing waves on Maui.

Napili Kai's quarter-mile white-sand crescent is arguably the prettiest beach on the island, but some might be put off by the resort's well-preserved '70s plantation-style decor, with lots of rattan, in all 163 rooms. Practical amenities such as a laundry facility (with free detergent) and bath products made from local coconut, ginger, and papaya are a nice touch for the core clients (many of whom are quite wealthy but interested in value) who return year after year with children and grandchildren. Most of the employees have worked here for more than 20 years, which adds to the sense of deep-rooted comfort. The restaurant menu includes fresh, healthy fare, but everybody's favorite is a stack of melt-in-your-mouth macadamia nut–and-banana pancakes with coconut syrup. The Masters of Slack Key concerts also take place here weekly.

The modern incarnation of the Paia Inn opened in 2008 in the cutest former plantation town in all of Hawaii. It's a welcome addition to Maui's hip north shore—home to Owen Wilson and Laird Hamilton—where there were previously few hotels. Owner and architect Michael Baskin designed the five rooms with Asian-inspired teak furniture, European bedding, perhaps a few too many colorful paintings by local artists, and the usual tech perks (flat-screen TVs, free Wi-Fi). Scones from Anthony's—the surfer mainstay located across the street—accompany coffee in the lounge each morning, and the restaurant's low-key menu of sandwiches and smoothies is available for room service. The little stretch of beach right in front of popular surf break Tavares and Paia's many shops, cafés, and restaurants are a two-minute walk away. (You can park the car and not move it until you leave.) Reasonable rates (starting at $169 per night), and a location that dials you into local life, make it easy to overlook the only potential downside—the intimacy of this historic two-story building means that sounds from other guests can occasionally intrude. On the upside, it's also easy to make friends with fellow travelers.

Pure Maui dials you into your destination by prescreening rental villas and your needs and desires, lining up a staff to match. The agency's 25-plus standout properties include the to-die-for '70s party house on a marine preserve, Ahihi Bay Hideaway, and the Kanaha Beach estate in the millionaires' enclave of Spreckelsville. Pure Maui can arrange chefs, massage therapists, mountain biking or hiking tour guides, fishing or dive boat captains, surf instructors, yoga or hula masters—even a life coach (or would that be a vacation coach?). If ordering up your holiday à la carte is too overwhelming, tweak one of the company's fitness, family-friendly, or romantic packages to suit your wants and needs. Once you arrive, the staff acts as your personal concierge and can make changes to your itinerary, in case you'd rather sleep in than take that four-hour waterfall hike. And if there's something you want to try that's not on the list of services (stand-up paddling, perhaps?), Pure Maui will do its best to make it happen. Celebrities love this outfit for its discretion—especially now that paparazzi hide in the bushes in Maui too—but it's also dedicated to taking you off the beaten track. (And the staffers are as ridiculously good-looking as they are qualified.)

This 570-room resort reopened in December 2007 after a much-needed Hawaiian make-under. The $180 million renovation added a spa, refreshed the public spaces, and replaced the dated and out-of-place preppy guest-room decor with contemporary furnishings in simple dark wood, muted tropical prints, and some wacky lamps. The Banyan Tree restaurant has also been spruced up, and its menu of Pacific Rim dishes with a molecular-gastronomy twist puts it in the running for the title of Maui's top restaurant. The Ritz-Carlton's location in remote Kapalua—the community beyond Lahaina, Kaanapali, and Napili—is both the worst and best thing about it. (Kapalua is a 45-minute drive from the Kahului Airport, but a mere five minutes from the West Maui Airport, which serves inter-island flights only.) To occupy those who don't want to just lie on the beach, there are two 18-hole golf courses, a historic pineapple plantation, a 10,000-square-foot three-tiered pool (with a 20,000-square-foot sundeck), six tennis courts, and an adventure center with a two-mile-long series of zip lines. Lahaina and Kaanapali are close by, as is the famous surf break of Honolua Bay—not really a swimming spot, but if the surfers are out, it's a prime location for spectators.

Located on the same stretch of sugar-sand Wailea beachfront as the Four Seasons and the Grand Wailea, the Marriott may be the best deal on the island. Thanks to a multimillion-dollar renovation completed in 2006, gone are the stale, dated interiors that practically screamed budget. The extensive face-lift has delivered an almost all-new resort, with sophisticated island decor in beige and brown tones, structural changes to improve the lobby, a new restaurant—the second location of Lahaina's popular foodie hangout, Mala Wailea—and a spa and fitness center. It still doesn't have the cachet of its five-star neighbors, but the Marriott is a poor relation no longer. If the view is a priority, spring for an oceanfront room—spending the same amount next door will only get you windows onto the Four Seasons's gardens.