Wailea Area

(877) 875-5036 or (808) 573-1234
3550 Wailea Alanui Dr, Wailea
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This 15-acre beachfront resort setting was completed in 2013, making the Andaz Wailea’s newest resort. The buildings are modern in both style and décor while still embracing the resort’s beachfront location. Their modern lobby is where every guest is personally greeted with a lei. There’s even a large “sandbox” (actually a sand-covered floor area) to hang out in and dip your toes into while you wait for your room. 

Outside, the three cascading infinity pools ensure great ocean views no matter where you plop down, while the lagoon pool at the bottom gives keiki plenty of space to frolic. They pass out complimentary snacks in the afternoons. The relaxed atmosphere extends across the property, which doesn’t feel as busy as some of the other Wailea resorts, even when full.

(866) 540-4456 or (808) 875-4100
4100 Wailea Alanui Dr, Wailea
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Let’s start with the reaction that almost everyone has when they approach this resort: Wow, this is a really goofy looking place! The impression is one of Ali Baba and the 40 Thieves meets King Kamehameha. According to the resort’s story, the developer asked the architect to create something that blends with the land. This is the result, a mix of Hawaiian and Moorish design. (For those who missed the Moors in geography class, think Casablanca.) Once you get inside, however, you realize that everything about the resort screams money, as if the developer opened a vault and poured money onto the floor. The results are impressive. Everything feels expensive.

(800) 334-6284 or (808) 874-8000
3900 Wailea Alanui Dr, Wailea
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Oh, my, where do we start? We’re fearful of sounding like drooling stooges for the Four Seasons, but Four Seasons Resort Maui is our favorite resort in Wailea.

When you walk in, you can actually feel the tension falling from your limbs. It soon becomes evident why. Here, they did everything right. Four Seasons Resort Maui at Wailea is immaculate and lovingly cared for. The smallest details seem to have been anticipated. The grounds are impeccable. Not a dead leaf or blade of grass in sight. The staff here is the most professional we’ve seen and seem genuinely concerned about your happiness. There are two and a half employees for every room. (It’s getting harder and harder to find those half employees.

(800) 367-5246 or (808) 891-6200
155 Wailea Ike Pl, Wailea
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Though not at the ocean’s shoreline, this condo is still in dreamy Wailea, and the units are large and comfortable. Many have very nice touches inside. Upstairs units have high vaulted ceilings at this 3-story walk-up property. Many units have fine golf course views, and all have discounts at the South Maui golf courses and the Wailea Tennis Club.

The main rental agent, Destination Residences, has extra services such as private chefs, various food packages with local specialty items, fresh flowers, wines and spirits, special event cakes and rental cars available from $36 and up per day.

Housekeeping is done every three days. A few units have room safes. 1/2s (714–1,069 sq. ft.) are $159–$389, 2/2s (1,182–1,371 sq. ft.) are $209–$489, 3/2s (1,698 sq. ft.) are $279–$659.

(800) 888-6100 or (808) 875-1234
3850 Wailea Alanui Dr, Wailea
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Words that describe this place are: wow, huge, awesome, overwhelming, crowded, fun. Grand Wailea is indeed one of the largest resorts on Maui. They took every dream and whim that the designers could come up with and sprinkled in a half billion dollars or so (give or take a hundred million—I mean, who’s counting when it gets that high?). The result is an outrageous, exotic tropical playground.

When you drive up, you are greeted by a waterfall that would look natural along the road to Hana. (In fact, one of the tour companies shows this waterfall in their jungle tour of Hana brochure—shame on them.) Once you’ve checked in, you just gotta check out the pools. Imagine nine interconnected pools with a current running between many of them.

(877) 346-6534 or (808) 856-2000
146 Hoolei Circle, Wailea
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This gated 30-acre condo property is a series of buildings in three terraced rows on a hillside across the road from the Grand Wailea. (Their numbering scheme is so strange, it can’t be explained.) The views range from garden view at the front to full ocean view at the back of the property (though it is over the rooftops). Some of those back row views are quite spectacular from the huge lanais, which open up entirely into the living space via a sliding wall of glass (with optional sliding srreen) and Sub-Zero fridge.

The units are all enormous, 2-story three-bedroom units with 596–705 sq. ft. of lanais and their own internal elevator from the private garage level. The kitchens are huge and have top-of-line appliances and everything you need to cook up a gourmet meal. Each bedroom has its own ensuite bath.

(866) 970-4167 or (808) 874-0500
555 Kaukahi St, Wailea
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This is the forgotten 15-acre Wailea resort. Most who live in South Maui have no idea that this place even exists. Instead of an oceanfront location, they’re up the hill, affording sweeping ocean views. Molokini and Kaho‘olawe look incredible from up here, and most rooms take advantage of these views. They are an adult-only resort. There are many fitness classes available on site, even aerial silk yoga classes. Their fitness room certainly has one of the grandest views we’ve ever seen (it might even inspire you to work out longer). They have a free shuttle to take you around Wailea and to the beach where an employee will supply you with a chair, towels, umbrella and water. They also rent snorkel gear, SUPs, boogie boards and kayaks at the beach.

(800) 688-7444 or (808) 879-5800
3200 Wailea Alanui Dr, Wailea
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Built in the early ’90s, these condos are an odd-looking modular design with unusual but comfortable interior layouts. Most units are adequately furnished and clean, but some really should be updated for this price. Rooms can get hot in units that have A/C only in the bedrooms (some have added it elsewhere.) Outrigger charges extra for the full A/C units (if available)— $15 for a 1/2 and $20 for a 2/2 per night—so keep those windows open to grab some of the typical afternoon Wailea breezes.

Best ocean views are from buildings 11, 12, 14 and 15, and upper floors are better. They have different floor plans, and floor plan “C” has a bizarre twist in a few units. The bathtub in these units is a Japanese soaking tub, and it’s located in the bedroom right next to the bed.

(800) 367-5246 or (808) 891-6200
4400 Makena Rd, Wailea
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The location of this condo sure is amazing—right next to Polo Beach. In fact, because it’s so close to the water and also so close to where you park your car, it’s popular with folks who don’t want to walk much.

The building is shaped in a series of notches, so if you get an oceanfront unit, ask for one of the notches closest to the water. (The front notches are called Prime Oceanfront and are the priciest.) Layouts are pleasing with both living room and the master bedroom next to the ocean, so you get to live and sleep to the sounds of the ocean. Ocean view units are farther back, but the angle of the building allows for good views from most units. There may be some stairs in your unit.

(888) 859-8262 or (808) 879-1922
3700 Wailea Alanui Dr, Wailea
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This is the only major Wailea-area resort that’s not on a sandy beach. The property sits on a rocky, elevated stretch of shoreline, but two corners of it are adjacent to beaches (the lovely Wailea Beach to the south and Ulua to the north), and the sand is easily accessible with a short walk. The resort’s buildings are spread out over 22 acres of rolling green lawns that never feel crowded. Five pools, including an adults-only infinity pool (no talking on cell phones allowed) and an adventure pool with waterfalls and four waterslides. One of those is 325 feet long (currently the longest resort waterslide in Hawai‘i), and another is 240-feet. A real blast— great for kids and kids at heart.

Generous room designations: Many “garden view” rooms have ocean views, and many “ocean view” rooms would count as “oceanfront” elsewhere.

(866) 384-1366 or (808) 891-4500
3800 Wailea Alanui Dr, Wailea
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Finished in 2006, these luxury gated condos are so exclusive that you need a key to both get in and out of the resort and the elevators. It’s adjacent to the Shops at Wailea and the Grand Wailea Resort (you can access both with a provided key). It consists of eight buildings, including a 5-story building that contains the “penthouses,” and seven 2-story buildings housing the villas. Penthouses are farthest from the ocean, and views are best from the fourth floor or above. Villas A and B are closest to the ocean.

The contemporary Hawaiian-style buildings have lush, tropical grounds with lots of mature plants.

(800) 367–5246 or (808) 891-6200
3300 Wailea Alanui Dr, Wailea
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This is one of the less impressive Wailea condo properties, although room classifications are more than fair with decent ocean views from some of the so-called garden view units. Also, the 34 acres of grounds means that upper village units are a 10-minute walk from the beach. Even units closer to the beach may be a 5-minute walk. The rooms we saw were of good quality from the agent we list.

This complex is fairly popular with families, and amenities such as a BBQ on each lanai, paddle tennis (short tennis court) and shuffleboard confirm their target market. Their covered pavilion by the beach is great for families with kids. You have access to a kitchen there, so basically you don’t have to go back to the condo to eat.

(800) 367-5246 or (808) 891-6200
10 Wailea Ekolu Pl, Wailea
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This is an older condo property (built in the late ’70s), but it’s an excellent value. Although not oceanfront, you’re very close to several awesome Wailea beaches. Good distant ocean views, especially from the second floor. Units we saw were expensively furnished and very comfortable.

The main rental agent, Destination Residences, has extra services such as private chefs, various food packages with local specialty items, fresh flowers, wines and spirits, special event cakes and rental cars available.

Housekeeping is every third day. A few units have room safes. 1/2s (869–1,069 sq. ft.) start around $360, 2/2s (1,073–1,489 sq. ft.) start around $460. 2- or 7-night minimum. Note that in addition to the daily resort/service fee of about 10%, you are also charged a one time reservation fee.

(800) 367-5246 or (808) 891-6200
3600 Wailea Alanui Dr, Wailea
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Large, nicely furnished condos with an excellent location—this property works. This is what many people think of when they contemplate a condo in Wailea. Goodies here include a short stroll to sandy Ulua Beach, a cement beach path that connects you to other Wailea resorts and restaurants, and a BBQ on each lanai. They have a fantastic covered pavilion with plenty of tables and a full kitchen next to the beach, along with BBQs. There is also a paddle tennis (short tennis) court and a putting green.

The main rental agent, Destination Residences, has extra services such as private chefs, various food packages with local specialty items, fresh flowers, wines and spirits, special event cakes and rental cars.