Wailea Homes with Pool

Wailea Homes with Pool

Welcome to Wailea, a stunning coastal community nestled in the heart of Maui, Hawaii. Known for its breathtaking ocean views, luxurious amenities, and world-class beaches, Wailea is the epitome of island living. This upscale neighborhood is characterized by its meticulously landscaped properties, upscale resorts, and vibrant cultural scene, making it a prime destination for those seeking both tranquility and adventure.

Wailea boasts some of the finest beaches in Maui, including Wailea Beach and Makena Beach, where residents can bask in the sun, snorkel in crystal-clear waters, or enjoy a leisurely stroll along the shoreline. The area is also home to renowned golf courses, upscale shopping at The Shops at Wailea, and a variety of dining options that cater to every palate, ranging from casual beachside eateries to gourmet restaurants.

For those dreaming of a home that embodies the essence of luxury, Wailea offers a selection of exquisite properties, many featuring private pools that allow for relaxation and entertainment in your own oasis. Imagine lounging by your sparkling pool surrounded by lush tropical landscaping, all while enjoying the gentle Maui breeze and the stunning sunsets that paint the sky in vibrant hues. With homes that seamlessly blend indoor and outdoor living, Wailea is perfect for both families and individuals who appreciate the finer things in life.

Whether you are looking for a permanent residence or a vacation retreat, Wailea is the ideal place to call home. Experience the magic of island living and discover the charm of this extraordinary community today!

Newest Wailea Homes with Pool

3200 Wailea Alanui Dr Unit 502, Kihei
$1,190,000
2 Beds ⋅ 2 Baths ⋅ 411174 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
PALMS AT WAILEA open-concept 2B|2B fully furnished condo features a private second-floor setting with an expansive double lanai surrounded by lush tropical foliage with a glimpse of the ocean; the perfect environment for Maui’s indoor-outdoor lifestyle. Filled with natural Maui light, it features beautiful tile flooring, two split-system AC systems, updated bathroom vanity, a seamless indoor-outdoor kitchen layout and a conveniently located assigned parking space. The exceptional location near Keawakapu Beach features beautifully landscaped grounds, a resort-style pool and spa nearby championship golf courses, tennis, pickleball, ocean activities, hiking, world-class resorts, fine dining and exclusive shopping at the Shops at Wailea and the Wailea Village. A rare opportunity offering an ideal blend of location, space, privacy, and value in the heart of the highly-desired Wailea Resort on Maui. Flexible options include vacation rentals, full-time residency or enjoyment as a second home.

3200 Wailea Alanui Dr Unit 502, Kihei

Listing courtesy of Compass-W.

155 Wailea Ike Pl Unit 151, Kihei
$950,000
1 Beds ⋅ 2 Baths ⋅ 411170 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Welcome to Grand Champions Unit 151, a beautifully renovated ground-floor one bedroom two bath condominium overlooking the first fairway of the Wailea Blue Golf Course. Enjoy spectacular year round Maui sunsets, tranquil golf course views, and a peekaboo ocean view from your private lanai. This tastefully updated residence features an open floor plan, stainless steel appliances and a queen Murphy bed for additional guests. This unit is being offered fully furnished and turn key, in a prime location ready for you to enjoy! Grand Champions offer two pools, spas, and BBQ areas surrounded by tropical landscaping. Ideally located in the heart of Wailea, minutes from world class beaches, golf, shopping and dining.

155 Wailea Ike Pl Unit 151, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3870 Wailea Ekolu Pl, Kihei
$4,250,000
3 Beds ⋅ 4 Baths ⋅ 411166 MLS ⋅ Fee Simple Tenure
3870 Wailea Ekolu Pl. presents a rare opportunity to own a luxury ocean-view home in Wailea Golf Estates, one of South Maui’s premier gated communities within the prestigious Wailea Resort. Positioned on an exceptional lot overlooking the ocean, this 3-bedroom, 3.5-bath residence captures panoramic views of Kahoolawe, Lanai, Molokai, and Molokini. Designed to maximize its breathtaking setting, the home features a functional floor plan, ensuite bathrooms in every bedroom, and seamless indoor-outdoor living. Enjoy Maui’s spectacular sunsets and seasonal whale watching from the spacious entertaining lanai, private swimming pool, and spa.The gated Wailea Golf Estates neighborhood is set among the scenic fairways of the Wailea Blue Golf Course, offering a desirable setting within one of Maui’s most sought-after resort communities. Ideally located just minutes from South Maui’s beautiful beaches, including Keawakapu Beach and Wailea Beach, the property also offers convenient access to championship golf courses, fine dining, luxury resorts, and upscale shopping at The Shops at Wailea. Whether seeking a primary residence or a private island retreat, 3870 Wailea Ekolu Pl. offers exceptional ocean-view living and the opportunity to enjoy the best of the Wailea lifestyle.

3870 Wailea Ekolu Pl, Kihei

Listing courtesy of Hawaii Life (W).

3600 Wailea Alanui Dr Unit 207, Kihei
$2,395,000
1 Beds ⋅ 2 Baths ⋅ 411159 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua I A BLDG.
Enjoy the expansive ocean view over the tropical landscaping from the living area, large covered lanai and the primary suite of this spacious 1 BD/2BA ground floor unit. Wailea Elua 207 is a well maintained condo which is being sold tastefully furnished. Additionally, this unit has been updated with a new AC unit, hot water heater & dishwasher as well as two recently replace sliding doors & screens. As an added bonus there is a large walk-in storage area just inside the entrance. The Wailea Elua community is one of the few low-density, beachfront properties in Wailea. Enjoy the two pools, heated spa, paddle/tennis courts, fitness center pavilion, beachside BBQ area, putting green and manned & gated entry. Wailea Elua Village is situated right on world-famous, Ulua Beach and on the 1 1/2 mile Wailea beachfront boardwalk. Just a short distance to five-star hotels, fine dining, and the Shops at Wailea, Wailea Elua units are zoned Hotel Resort and allow Owners the ability to use the property for Short Term Vacation Rentals (STVR) to generate income if desired.

3600 Wailea Alanui Dr Unit 207, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

10 Wailea Ekolu Pl Unit 1403, Kihei
$975,000
1 Beds ⋅ 2 Baths ⋅ 411151 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekolu BLDG.
Enjoy the relaxed island lifestyle at Wailea Ekolu #1403, an updated, fully furnished one-bedroom, two-bathroom condo offering ocean views and convenient ground-level living with no stairs. The thoughtfully appointed interior features two split AC units, one in the living room and one in the bedroom, providing comfort throughout the year. Two separate lanais extend the living space outdoors, creating inviting spots to enjoy the tropical surroundings, morning coffee, or sunset evenings. Ideally located near one of the community pools and BBQ areas, this residence offers easy access to some of Wailea Ekolu’s most desirable amenities. Owners have the opportunity to join the Wailea Golf Club membership, adding another way to enjoy the resort lifestyle. Set within the renowned Wailea resort community, Wailea Ekolu #1403 is conveniently close to beautiful South Maui beaches, championship golf courses, upscale shopping, and a variety of restaurants. Whether you’re seeking a Maui getaway, a comfortable island retreat, or a place to enjoy the best of Wailea, this property offers an appealing combination of comfort, convenience, and location.

10 Wailea Ekolu Pl Unit 1403, Kihei

Listing courtesy of Hawaii Life (W).

86 Poailani Pl Unit Unit 32, Kihei
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 411149 MLS ⋅ Fee Simple Tenure
Also listed as condominium MLS# 411148. Experience effortless Wailea living in this beautifully appointed 4-bedroom. 4,5-bath single-level ocean-view residence in Kanani Wailea. Offering 2,175 sq. ft. of thoughtfully designed living space, the home enjoys beautiful ocean views and spectacular Maui sunsets. The well-appointed kitchen features a Sub-Zero refrigerator and wine cooler, along with Wolf cooktop, oven, and microwave. Sold fully furnished and move-in ready, each bedroom features its own en-suite bath. Recent updates include new flooring throughout and a beautifully remodeled primary bath. A secure private courtyard welcomes you and provides separate access to the 3-bedroom, 3.5-bath main residence and the attached guest suite, offering added privacy and a comfortable retreat for family and friends. Enjoy the convenience of a lock and leave condominium in a single family home. Ideally located near Wailea's world-class beaches, championship golf, luxury resorts, shopping, and dining, this exceptional residence offers a wonderful combination of ocean views, privacy, and relaxed Maui luxury. This is a Residential Condo.

86 Poailani Pl Unit Unit 32, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3200 Wailea Alanui Dr Unit 1207, Kihei
$1,349,000
2 Beds ⋅ 2 Baths ⋅ 411145 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
Palms at Wailea #1207 offers a rare chance to own a beautifully remodeled, fee simple 2 bedroom, 2 bath residence in one of Wailea’s most coveted communities, at a price point that is increasingly hard to find for a 2BR/2BA in Wailea. With a ground level entry, there is no climbing to an upper floor; simply walk in to a bright, airy interior refreshed with a tasteful renovation beginning in 2023, featuring elegantly remodeled bathrooms, new flooring, an in-unit washer and dryer, and air conditioning for year-round comfort. Privately set along the tranquil inner greenbelt, the spacious lanai opens directly onto lush, meticulously maintained grounds, inviting you to unwind in the gentle trade winds. This intimate, Mediterranean-style community is surrounded by gardens showcasing more than a hundred varieties of palms, with a resort-style pool, hot tub, BBQ area, fitness center, and clubhouse just steps from your door. World-renowned Keawakapu Beach is a short stroll away, and the prestigious Wailea Resort places championship golf, fine dining, boutique shopping, and South Maui’s celebrated beaches at your fingertips. Fully furnished, impeccably maintained, and truly turnkey, #1207 is a private retreat to relax and experience the very best of Wailea living.

3200 Wailea Alanui Dr Unit 1207, Kihei

Listing courtesy of eXp Realty.

173 Holokahiki Ln Unit 10B, Kihei
$2,495,000
3 Beds ⋅ 3 Baths ⋅ 411084 MLS ⋅ Fee Simple Tenure ⋅ Makalii At Wailea BLDG.
Experience modern coastal luxury living at Makalii at Wailea #10B. Centrally tucked away from any road awareness yet only moments from Polo Beach and Fairmont Kea Lani, this 2021-built 3-bedroom, 3-bathroom townhome features the gated community's largest floor plan (1,802 sq ft interior / 2,535 sq ft total) and includes a private guest casita. The main level offers an open-concept living space, a gas kitchen, a guest suite, and two lanais with ocean and garden views, plus a hard-plumbed gas line for grilling. Constructed with low-maintenance premium materials that are sure to impress, the property includes an attached garage and additional driveway parking. Enjoy world-class community amenities, including one of Wailea’s most expansive infinity pools, ocean-view fitness center, hot tub, saunas, and steam rooms. Schedule your private showing today! This incredible opportunity will not last!

173 Holokahiki Ln Unit 10B, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3950 Kalai Waa St Unit A 101, Kihei
$1,024,730
2 Beds ⋅ 2 Baths ⋅ 411053 MLS ⋅ Fee Simple Tenure ⋅ Wailea Fairway Villas BLDG.
Experience effortless island living in this beautifully updated and fully furnished 2-bedroom, 2-bath ground floor end-unit townhome in Wailea. Enjoy open-concept living with engineered hardwood flooring, custom cabinets, custom blinds, quartzite countertops, accent lighting, full sized stacked washer and dryer, and a split A/C system. This tastefully appointed unit has also been recently painted. Residents of Wailea Fairway Villas enjoy outstanding amenities including a heated saltwater pool, reservable clubhouse with full kitchen, bbq grills, hot tub, and a fitness center. On site carwash area, bike racks, board/kayak storage are also available. Ideally located close to Wailea’s championship golf courses, pristine beaches, premier shopping and dining.

3950 Kalai Waa St Unit A 101, Kihei

Listing courtesy of eXp Realty.

4000 Wailea Alanui Dr Unit 1104, Kihei
$7,999,000
3 Beds ⋅ 5 Baths ⋅ 411043 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
Rarely does a front row Wailea Point residence become available with this level of thoughtful, high-end upgrading. Unit 1104 delivers unobstructed, front-row ocean views from one of Maui's most coveted oceanfront communities, framed by soaring high ceilings that flood the living space with light and amplify the sense of openness. Every detail has been considered. Polarized, mitered glass windows preserve the breathtaking ocean views without sacrificing UV protection while two new air conditioning units keep the home cool and comfortable year-round. The kitchen has been beautifully upgraded with natural stone countertops and a new GE Monogram refrigerator. A Samsung Frame TV adds a sophisticated, gallery-like touch to the living space. The main floor offers two generously appointed bedrooms and three fully remodeled bathrooms, thoughtfully designed for comfort and everyday living. Ascend the impeccably crafted staircase to a spacious master suite retreat, complete with its own private lanai and two full bathrooms — a rare layout offering separation, privacy, and space to unwind while taking in the same front row ocean views. A private single car garage (Garage 1104-G) is included in the sale. Wailea Point remains one of South Maui's premier gated oceanfront communities, offering resort-style amenities, meticulously maintained grounds, and direct access to the Wailea coastal path. Set on almost 30 acres of lush tropical landscaping with fewer than five residences per acre, it offers an unmatched combination of privacy and beauty. Residents enjoy 24-hour gated security, four swimming pools, spa, pavilions, fitness center, tennis and pickleball courts, barbecue areas, walking paths, and beautifully maintained gardens. The community is ideally situated between the Four Seasons Maui and the Fairmont Kea Lani, with world-class beaches, championship golf, fine dining, and luxury shopping just moments away. This front row residence combines unbeatable location with move-in-ready upgrades and thoughtful design - a rare opportunity for discerning buyers.

4000 Wailea Alanui Dr Unit 1104, Kihei

Listing courtesy of Wailea Point Realty, Inc..

155 Wailea Ike Pl Unit 136, Kihei
$800,000
1 Beds ⋅ 2 Baths ⋅ 411042 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Desirable top-floor unit in Grand Champions, ideally located in Wailea. Featuring high ceilings and an inviting floor plan, this unit offers a bright and comfortable living space. Relax on the private lanai and enjoy beautiful garden and mountain views, peek-a-boo ocean views, and partial golf course views. Grand Champions offers two pools, hot tubs, and barbecue areas in a beautiful setting along the Wailea Blue Golf Course. Conveniently located near Wailea's beautiful beaches, golf courses, The Shops at Wailea, acclaimed restaurants, and the Wailea Tennis Club, this residence offers the perfect blend of comfort, convenience, and relaxed Wailea living.

155 Wailea Ike Pl Unit 136, Kihei

Listing courtesy of Hawaii 5-0 Properties, Inc..

3150 Wailea Alanui Dr Unit 2601, Kihei
$1,275,000
1 Beds ⋅ 2 Baths ⋅ 411034 MLS ⋅ Fee Simple Tenure ⋅ Wailea Palms BLDG.
Experience the exceptional Wailea lifestyle from this beautifully appointed 1-bedroom, 2-bath residence at Wailea Palms. Thoughtfully remodeled in 2013 with an eye for quality, craftsmanship, and timeless island style, this turn-key 1,022-square-foot ground floor condominium offers a seamless blend of sophisticated interiors and relaxed outdoor living and is being sold fully furnished. The kitchen features stunning custom Koa cabinetry, granite countertops, stainless steel appliances and a wine cooler. Throughout the residence, 18-inch porcelain tile flooring, dimmable recessed lighting, solid South African mahogany interior doors, and matching South African mahogany ceiling accents create an elegant yet comfortable ambiance throughout. The open living area is designed for easy island living and entertaining, while custom Koa built in storage within the pony walls allow for an organized solution to keep clutter out of sight. Step outside to an impressive 473-square-foot tiled lanai, where indoor and outdoor spaces come together beautifully. A convenient kitchen pass-through opens to the lanai where a teak storage cabinet and stone countertop are complete with a mini-fridge. Electric outdoor shades provide added comfort and help temper the afternoon sun while you relax overlooking the peaceful south greenbelt with glimpses of the Pacific Ocean. This spacious floor plan and generous lanai make this residence equally suited to quiet mornings, sunset cocktails, or entertaining guests. Every detail reflects the relaxed elegance for which Wailea is known. Wailea Palms offers an inviting resort-style setting with beautifully manicured tropical grounds, fountains, an ocean-view pool and spa, air-conditioned fitness center, putting green, and on-site property management. Just a short stroll from the residence, the pool pavilion provides an ideal place to unwind and enjoy the exceptional Maui climate. Beyond the property, enjoy all that the Wailea Resort lifestyle has to offer, including world-class beaches, championship golf, tennis, exceptional dining, luxury shopping, and year-round outdoor recreation. This is a distinctive Wailea residence offering space, quality, privacy, and an enviable Maui lifestyle.

3150 Wailea Alanui Dr Unit 2601, Kihei

Listing courtesy of Carol Ball & Assocs.

Start Your Search

How much is your home worth?

Get instant property value now!