Refine Search
Map
Sort by
$2,399,000
3 Beds ⋅ 3 Baths ⋅ 410693 MLS ⋅ Fee Simple Tenure
Welcome to Wailea Kai, where privacy, luxury, and effortless island living come together in one of Wailea’s most desirable gated communities. This immaculately maintained 3-bedroom, 2.5-bath residence feels both refined and relaxed, with soaring vaulted open-beam ceilings, abundant natural light, dark bamboo flooring, mahogany doors and cabinetry, granite countertops, and plantation shutters throughout. The open-concept living area flows seamlessly through expansive sliding glass doors to a lush tropical backyard and patio, creating an inviting indoor-outdoor setting for alfresco dining, entertaining, or unwinding beneath the Maui sky. The well-appointed kitchen features stainless-steel appliances, generous storage, a pantry, and casual dining nook, while split-system air conditioning throughout provides year-round comfort. Upstairs, the entire level is devoted to the spacious primary suite—a private sanctuary complete with a sitting area, walk-in closet, ensuite bath, and its own lanai. Just moments from Wailea Kai’s dedicated community park and an easy stroll to world-renowned Keawakapu Beach, the best of Maui’s coastal lifestyle is right outside your door, with white sand, turquoise water, and unforgettable sunsets just minutes away. Wailea’s acclaimed dining, luxury shopping, championship golf, tennis, and resort amenities are also close at hand. This private Wailea residence offers a comfortable setting for enjoying the beauty and convenience of life in one of Maui’s most sought-after communities.

30 Waikai St, Kihei

Listing courtesy of Romvari Realty Ltd.

$3,850,000
3 Beds ⋅ 4 Baths ⋅ 410561 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
Discover elevated luxury at Villa T-1, the best priced property and sole end-unit available today at Ho’olei. Boasting the community’s largest floor plan—the sought-after Hibiscus layout—this spacious split-level townhome blends 3,076 sq.ft. of exquisitely refreshed interior space with approximately 700 sq.ft. of covered lanai for seamless indoor-outdoor living. Positioned in a coveted front-row location, you are steps away from Ho’olei’s world-class amenities, featuring a lagoon-style pool with a dramatic 19’ waterfall, swim-in grotto, dual spas, fitness facility, and poolside entertaining pavilion. Just moments from Wailea Beach, fine dining, championship golf, and shopping, this beautifully furnished residence offers exceptional privacy, a place to call home in Maui, alongside a stellar, proven rental track record.

24 Hoolei Cir Unit T-1, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$3,500,000
3 Beds ⋅ 2 Baths ⋅ 410112 MLS ⋅ Fee Simple Tenure
Every once in a long while, a home feels less like a property and more like a discovery. Rebuilt from studs in 2019, this better than new single level, no steps Wailea retreat pairs effortless accessibility and wide 36" doorways with the quiet polish of a private resort. Light filled interiors, soaring eight to twelve foot ceilings, and walls of Fleetwood glass open seamlessly to nearly a thousand square feet of lanai living. No expense spared with the choice of long lasting durable and as well as beautiful Monier tile roof, copper downspouts and gutters with French drains throughout. The finish level is exceptional, with large format Italian porcelain floors, a Poggenpohl kitchen with SubZero and Miele, and spa inspired baths featuring Toto washlets and Dornbracht fixtures. The primary suite opens directly to garden views, a shimmering saltwater pool and spa, and an outdoor shower wrapped in teak, while a thoughtful split bedroom layout offers guests true privacy. With owned photovoltaic, upgraded electrical, central air, remote sunshades, xeriscape landscaping, and copper landscape lighting, all just moments from Keawakapu Beach, Wailea's best shopping, and world class golf and tennis, this is turnkey Wailea living at its most refined and effortless. Outfitted with DWR (Design Within Reach) high-end furnishings, 39 Hoawaa is a turnkey residential experience.

39 Hoawaa Way, Kihei

Listing courtesy of Maui Luxury Real Estate LLC.

$999,500
2 Beds ⋅ 2 Baths ⋅ 409449 MLS ⋅ Fee Simple Tenure ⋅ Wailea Fairway Villas BLDG.
Best Value in Wailea! Come fall in love with this beautifully remodeled Wailea Fairway Villas second floor unit. Attention to detail is evident throughout from the abundance of recessed LED lighting to the built-in closet organizers in each bedroom, the 3 split A/C system, built-in storage cabinets, and even a Pulse Showerspa shower system. Freshly painted with a warm and inviting color palette which creates a comfortable and relaxed feel. You will love sitting outside on the private lanai surrounded by lush tropical foliage. A rare added bonus is the insulated attic which provides an abundance of storage. This is an amazing opportunity to own in a quiet Wailea complex with fantastic amenities, close to world famous beaches and shopping. Unit comes tastefully furnished and turnkey. Call your favorite realtor today.

3950 Kalai Waa St Unit U202, Kihei

Listing courtesy of Berkshire Hathaway Maui Prop-W.

$1,100,000
1 Beds ⋅ 1 Baths ⋅ 409361 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekahi I BLDG.
This charming, private ground-floor 1-bedroom, 1-bathroom end-unit is flooded with natural light and has been meticulously maintained. From the spacious living area, kitchen, and extended tiled lanai, you'll enjoy beautiful views of the lush garden. The unit perfectly blends indoor and outdoor living, with direct access from the kitchen that's ideal for alfresco dining. It's like stepping into your own "Secret Garden of Maui." When it's time for the beach and some sun, this unit offers a short 4 minute stroll down to Maui's famous Keawakapu beach. The kitchen boasts stainless steel appliances, including a wood-clad refrigerator, warm-toned ceramic tile countertops, and a full-height backsplash. The natural wood louvered sliders and bi-fold doors enhance the unit's rich and inviting atmosphere. The bedroom offers access to a private garden lanai, creating a peaceful retreat. The custom bathroom features a floor-to-ceiling tiled, glass-enclosed shower with decorative seashell accents. A Murphy bed adds versatility, providing a second sleeping area. Wailea Ekahi is known for its lush tropical landscaping, mature plantings, and a variety of amenities, including multiple pools and tennis courts. The Keawakapu beachfront pool and gathering pavilion are truly exceptional. Nearby, the renowned Shops at Wailea offer fine dining, shopping, and art galleries. Wailea also provides world-class opportunities for golf, tennis, diving, snorkeling, horseback riding, hiking, and is close to luxurious spas.

3300 Wailea Alanui Dr Unit 25C, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,025,000
2 Beds ⋅ 2 Baths ⋅ 409215 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Welcome to your serene escape in the heart of paradise! Grand Champions unit #10 is a 2-bedroom, 2-bath condominium with a lock off option creating multiple living or rental arrangements_ Located on the top floor with soaring ceilings enhances the sense of space and elegance, making the condo feel even more inviting. The open concept living space has a fully-equipped kitchen, dining and living area that leads to the large private garden view lanai. There is a king size bed in the primary bedroom, a queen size bed in the second bedroom and a queen sleeper sofa in the living room. Grand Champions has 2 swimming pools, spas and 6 BBQ's in the complex. This fully furnished turn key unit is nestled within the lush, tropical landscape a tranquil garden view, ensuring peace and privacy while being just minutes away from world-class beaches, golf courses, shopping, and dining. Make Grand Champions #10 your home or your home away from home and enjoy all that Maui has to offer!

155 Wailea Ike Pl Unit 10, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$1,435,000
2 Beds ⋅ 2 Baths ⋅ 409160 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
Discover the perfect blend of comfort, style, and location at Palms at Wailea #1207. This beautifully updated 2-bedroom, 2-bath ground-level condominium enjoys a prime position within the complex, nestled along the serene inner greenbelt. The spacious lanai opens directly onto the lush greenbelt, creating a seamless indoor-outdoor living experience ideal for relaxing or entertaining. The unit offers a peaceful, private setting while being just a short stroll to the resort-style pool, hot tub, and BBQ area. Inside, contemporary upgrades enhance every space — both bathrooms were tastefully remodeled in 2023, and new flooring installed in 2024. The primary bedroom features a split AC system for cool comfort year-round. Fully furnished and ready to enjoy, this turn-key residence is located within the exclusive Wailea Resort, minutes from world-class beaches, championship golf, fine dining, and boutique shopping. Palms at Wailea #1207 delivers the ideal Maui lifestyle — private, modern, and perfectly positioned in one of Wailea’s most desirable communities.

3200 Wailea Alanui Dr Unit 1207, Kihei

Listing courtesy of Hawaii Life (W).

$1,250,000
2 Beds ⋅ 2 Baths ⋅ 408354 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekolu BLDG.
Relax and Enjoy Ultimate Privacy! Enter your new Wailea place of peace, serenity and tranquility. This 2 Bedroom 2 Bath Vacation Rental Condo has been beautifully renovated and it is nestled in a lush tropical and private setting in Wailea. Surrounded by vibrant greenery and swaying palm trees, this condominium offers a peaceful retreat where you can relax and unwind. The interior is thoughtfully designed with wonderful modern updates that blend comfort with style. Enjoy breathtaking glimpses of the ocean from your private covered lanai, a sanctuary that creates the perfect backdrop for your morning coffee or serene evening sunsets. The condo's atmosphere of complete tranquility is ideal for relaxation, while this prime location places you just moments from the World Class Beaches, shopping, and dining that make the Wailea Resort a world renowned destination. This vacation rental offers the ultimate getaway for those looking to experience the beauty and tranquility of Maui in a luxurious, private setting. Don’t hesitate - this is the beautiful hideaway you have been dreaming of!

10 Wailea Ekolu Pl Unit 1603, Kihei

Listing courtesy of Hawaii Life (W).

$1,275,000
2 Beds ⋅ 2 Baths ⋅ 407528 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
Enjoy the Wailea lifestyle from this ground-floor, fee-simple 2-bedroom, 2-bath condominium at The Palms at Wailea, one of the most affordable fee-simple, vacation-rentable two-bedroom condominiums currently available in Wailea. Just a short walk to Keawakapu Beach Park and the Wailea Beach Path, and minutes from The Shops at Wailea, championship golf, tennis, luxury resorts, spas, and exceptional dining, this South Maui location places many of Wailea's most popular attractions within easy reach. Offering approximately 1,242 square feet of living space, this residence features a spacious primary suite with an ensuite bath and separate soaking tub, comfortable living and dining areas, and a kitchen with a convenient pass through to the oversized lanai. The oversized lanai opens to a spacious lawn, creating a more open feel and a comfortable outdoor setting. A short set of stairs from the parking area leads to the residence, which enjoys an elevated setting while offering the convenience of ground floor living. Currently operating as a Maui short-term vacation rental, this well-cared-for residence is furnished and equipped for continued vacation rental use from day one. The Palms at Wailea offers beautifully maintained tropical grounds, a resort style pool and spa, barbecue areas, and an onsite vacation rental management company for owners who prefer the convenience of an onsite team.

3200 Wailea Alanui Dr Unit 1605, Kihei

Listing courtesy of Island Sotheby's International Realty(W).

$1,045,000
2 Beds ⋅ 2 Baths ⋅ 403638 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
This lovely remodeled and cared for 2 bedroom/2 bathroom Grand Champions unit speaks of Hawaiiana and is being sold 'Turn Key' Furnished. Unit #140 is upper-level with vaulted ceilings and lives large. The sheer scale and volume of space adds a sense of elegance and comfort to the living experience. Vernal and serene truly describe the setting. There are peaceful, green and pastoral views from the unit with a small southwest ocean view from the glass railing surrounded lanai area. There is a lovely, high quality, richly textured and patterned carpet throughout. Additionally, there are three zones of split-system climate control. There is an abundance of natural wood cabinetry complimented by the granite countertops in the spacious stone-like tiled floor kitchen. The stainless-steel appliances contrast nicely with the wood cabinetry and full height stone & glass tiled back splash. The light filled primary bedroom faces south and affords an abundance of peaceful lushly landscaped views and fresh air. The primary bathroom has a cherry wood vanity, dual porcelain undermount sinks and a six-inch tall granite backsplash. The primary shower area features floor to ceiling stone-like tiles and a custom 'Bird of Paradise' tile design. The beautifully appointed guest bedroom features two corner windows allowing for lots of natural light and includes 8 ft tall mirrored closet sliders. The en-suite guest bathroom features cherry cabinetry along with lovely granite countertops and an onyx tiled backsplash. A functionally efficient feature is that the washer & dryer are located in the exterior lanai closet thus not taking up extra space and eliminating noise and humidity. The richly landscaped entrance to Wailea's Grand Champions Condominium, where one is greeted by a fabulous water feature filled with magnificent mosses, sets the tone for the entire quiet enclave. Additionally, there are two pool area facilities featuring spas, BBQ’s and changing rooms. The complex is surrounded on three sides by the Wailea Blue Golf Course and is located conveniently to world class beaches, dining and shopping.

155 Wailea Ike Pl Unit 140, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.