Wailea, HI Homes for Sale with Pool

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  /50

  $999,000

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  2777 S Kihei Rd Unit 218, Kihei, HI 96753

  Maui Kamaole boasts gorgeous ocean views stretching toward the West Maui Mountains, perfectly positioned for breathtaking sunsets, and is ideally situated between the complex’s two stunning pool areas and outdoor BBQ areas. The spacious floor plan offers generous living space along with three separate lanais, perfect for embracing Maui’s indoor-outdoor lifestyle. The condo is being sold fully

  Claudia Garcia Maui International R E Srvs

  2777 S Kihei Rd Unit 218, Kihei, HI 96753
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  $4,900,000

  $300K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,808 Sq Ft

  4000 Wailea Alanui Dr Unit 2802, Kihei, HI 96753

  An absolutely exquisite property in every way, Residence 2802 at Wailea Point boasts a fabulous location with breathtaking ocean, island, beach and coastal views facing iconic Molokini Island and stretching from the South Maui coastline to Lanai Island. This upper floor plan features soaring ceilings and an open, airy design. The elegant mitered glass bay windows majestically frame the already

  Dave Wagner Wailea Point Realty, Inc.

  4000 Wailea Alanui Dr Unit 2802, Kihei, HI 96753
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  $2,500,000

  Open Sun 9:30AM - 6PM $195K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,902 Sq Ft

  3142 Waiea Place, Kihei, HI 96753

  Wailea Kai is one of the closest communities to the beach! 3 BR 2.5 BA with a pool and easy walking distance to Keawakapu Beach. This recently updated home offers a unique living style with the master on the main level and 2 bedrooms tucked away separately with a jack & jill bath, all 3 with vaulted ceilings. The master has a large lanai that overlooks the pool and lawn area. A major remodel of

  Terence Alling Coldwell Banker Island Prop-Ku

  3142 Waiea Place, Kihei, HI 96753
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  $2,495,000

  • 3 Beds
  • 3 Baths
  • 1,802 Sq Ft

  209 Holokahiki Ln Unit 103, Wailea-Makena, HI 96753

  Welcome to Makalii one of Wailea’s newest luxury residences known for its mid-century modern design. This spectacular condominium (7C) is located on the upper row and is situated in the only building that that faces north, overlooking the Wailea Blue Golf Course with wonderful ocean/sunset views.The orientation of this building provides exceptional privacy and an abundance of natural light from

  Leslie Smith Hawaii Life (W)

  209 Holokahiki Ln Unit 103, Wailea-Makena, HI 96753
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  /45

  $2,550,000

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft

  24 Kai Malu Dr Unit 3-A, Kihei, HI 96753

  Experience elevated island living in this beautifully appointed condominium at Lai Loa Wailea, one of South Maui’s newest luxury communities. Purchased new in 2024, this fully furnished ocean-view residence offers an exceptional blend of modern design, refined finishes, and effortless lock-and-leave ownership in the heart of Wailea. Thoughtfully designed for both full-time and second-home living,

  Ryan MacLaughlin Island Sotheby's International Realty(W)

  24 Kai Malu Dr Unit 3-A, Kihei, HI 96753
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  $1,999,000

  $200K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft

  3161 Mapu Place, Kihei, HI 96753

  Welcome to your private tropical oasis in serene Maui Meadows. This remarkable and rare property spans over a 0.52-acre corner lot, offering a true resort-style experience with lush tropical landscaping that provides exceptional privacy and tranquility. This unique estate features three distinct dwellings, making it ideal for multi-generational living, rental income opportunities, or a private

  Jordan Smith Island Sotheby's International Realty(W)

  3161 Mapu Place, Kihei, HI 96753
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  $14,750,000

  $1M PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,803 Sq Ft

  19 Malukai Ln Unit 4, Kihei, HI 96753

  Step into a world of refined elegance and beachfront luxury in Maluhia at Wailea—a sanctuary within Wailea’s most exclusive beachfront enclave. Tucked behind the gates of this community of just 14 bespoke estates, this 4,800+ sq. ft. home is a fusion of contemporary sophistication and the raw, natural beauty of Hawaii. There are four exquisite bedrooms, including a lavish primary suite on the

  Josh Jerman Hawaii Life (W)

  19 Malukai Ln Unit 4, Kihei, HI 96753
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  /29

  $9,395,000

  • 3 Beds
  • 4 Baths
  • 3,666 Sq Ft

  144 Halau Place, Kihei, HI 96753

  Set behind the gates of Wailea Golf Estates, this like-new contemporary estate captures the essence of modern Hawaiian luxury. Spanning over 5,000 square feet of indoor-outdoor living, this single level home is designed as a seamless pavilion between architecture and nature, where walls of glass dissolve into tropical gardens and panoramic Pacific vistas. Also available to the qualified buyer is

  Mark Waite Compass-W

  144 Halau Place, Kihei, HI 96753
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  /19

  $490,000

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 719 Sq Ft

  2747 S Kihei Rd Unit B306, Kihei, HI 96753

  Top-floor corner unit in the highly sought-after “B” building at Kihei Shores—offering added privacy, excellent airflow, and no units above. This 2-bedroom, 2-bath residence features high ceilings and a bright, open feel, enhanced by fresh interior paint and new flooring in the main living and bedroom areas. The functional layout includes a spacious living area, private lanai, and AC. Originally

  Kokua Realty Kokua Realty LLC

  2747 S Kihei Rd Unit B306, Kihei, HI 96753
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  /50

  $3,589,000

  $206K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,742 Sq Ft

  24 Kai Malu Dr Unit 102 (3B), Kihei, HI 96753

  La’i Loa Luxury with Outstanding Ocean View! Wailea’s Newest Development and your golden opportunity to have it all is here! This gorgeous Turnkey Residence in La’i Loa comes with over $400K in luxury furnishings and decor - everything you need to begin the Maui life you’ve earned. Perfectly situated within the community, you will enjoy the pinnacle of island luxury in this exquisite turnkey

  Dale Richardson Hawaii Life (W)

  24 Kai Malu Dr Unit 102 (3B), Kihei, HI 96753
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  $2,750,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,574 Sq Ft

  197 Holokahiki Ln Unit 8A, Wailea, HI 96753

  Experience modern island living at Makalii 8A, a 3-bed, 3-bath contemporary townhome tucked away in a quiet corner of the complex, featuring refined new construction in the heart of Wailea Resort. This first offering is fully furnished, turnkey, and presented in immaculate condition. Thoughtfully designed with clean architectural lines and subtle mid-century influences, the residence offers 1,574

  Nancy J. Callahan Coldwell Banker Island Prop(S)

  197 Holokahiki Ln Unit 8A, Wailea, HI 96753
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  $11,745,000

  $750K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,814 Sq Ft

  3550 Wailea Alanui Dr Unit 801 (F2), Kihei, HI 96753

  Andaz Residences Unit 801 (F2) offers a rare opportunity to own one of the coveted private villas at the Andaz Maui Wailea Resort. Ownership combines the privacy of an oceanfront home with full access to the exceptional amenities of the Andaz Hotel including pools, spa, fitness center, beach service, concierge, and award-winning dining. These exclusive residences rarely come to market. This

  Anne Bakoulis Coldwell Banker Island Prop(S)

  3550 Wailea Alanui Dr Unit 801 (F2), Kihei, HI 96753
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  $1,000,000

  $250K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 680 Sq Ft

  2936 S Kihei Rd Unit 213, Kihei, HI 96753

  OWN PRIME MAUI REAL ESTATE! Kihei Surfside 213 is a direct oceanfront 1-bedroom, 1.5 bath condo in one of South Maui's most sought-after complexes—perfect for a vacation rental investment or personal enjoyment. This unit offers spectacular views of the Pacific Ocean and the West Maui Mountains. The open layout is light and airy, with large windows that bring the ocean right into your living

  Heather Zidell Compass-W

  2936 S Kihei Rd Unit 213, Kihei, HI 96753
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  $3,750,000

  • 3 Beds
  • 3 Baths
  • 3,839 Sq Ft

  3919 Waakaula Place, Kihei, HI 96753

  Imagine the possibilities! Framed by sparkling ocean, pool and sweeping panoramic views, while perched within one of South Maui's most prestigious enclaves, this 3-bedroom, 3-bath residence in Wailea Golf Estates offers a rare combination of privacy, elegance, and effortless island living. Relax and recharge with EV charging and the opportunity to add your own personal touches, making this a

  Geoffrey Cook Century 21 Island Homes

  3919 Waakaula Place, Kihei, HI 96753
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  $5,900,000

  • 4 Beds
  • 3 Baths
  • 3,059 Sq Ft

  19 Halapa Place, Kihei, HI 96753

  Experience practical elegance in this thoughtfully designed single level custom Wailea home, completed in 2021. Enjoy the magnificent & expansive ocean views, perfect for sunsets & whale watching (during whale season). Perfectly positioned at the top of Wailea in The Ridge at Wailea, a coveted neighborhood with just nine lots. This 4 bedroom, 3 bathroom home with a separate home office blends

  Sherrie Stinger Coldwell Banker Island Prop(S)

  19 Halapa Place, Kihei, HI 96753
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  $1,349,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  155 Wailea Ike Place Unit 78, Kihei, HI 96753

  Stunning ocean view, overlooking the Wailea Blue Golf Course, this gem is beautifully positioned in one of Wailea’s most sought-after resort communities—Grand Champions. This 2-bedroom, 2-bath, 1,056 sq. ft. condo is adjacent to Wailea Blue Golf Course hole 15. This second-floor residence features high vaulted ceilings, an expansive walk-in master closet, and a spacious shower designed for two.

  Sara Romvari Romvari Realty Ltd

  155 Wailea Ike Place Unit 78, Kihei, HI 96753
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  $2,395,000

  • 4 Beds
  • 3 Baths
  • 1,894 Sq Ft

  3236 Pikai Way, Kihei, HI 96753

  Welcome to 3236 Pikai Way, an exceptional single-level residence nestled within the exclusive gated enclave of Wailea Kai, just across the street from the golden sands of world-famous Keawakapu Beach. Situated on a quiet private cul-de-sac in Little Wailea Kai, this beautifully maintained 4-bedroom, 3-bath home offers the perfect blend of luxury, privacy, and effortless island living. Designed

  Keoni Fursse Kokua Realty LLC

  3236 Pikai Way, Kihei, HI 96753
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  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  2777 S Kihei Rd Unit 207, Kihei, HI 96753

  Spectacular ocean view from this very private lanai on the front row of Maui Kamaole. Updated kitchen with bamboo cabinet doors, granite counter tops & newer black appliances. Both bathroom shower walls have been re-tiled. New water heater. Beautiful Murphy bed in the guest bedroom. This has not been used as a vacation rental, but it would make a great one! Maui Kamaole offers 2 pools, 2 hot

  Roger Pleski Coldwell Banker Island Prop(S)

  2777 S Kihei Rd Unit 207, Kihei, HI 96753
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  $639,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  2575 S Kihei Rd Unit H101, Kihei, HI 96753

  1 bedroom, 2 bathroom condotel unit available for sale at the popular Maui Banyan in South Kihei, across from Kamaole Beach Park II. Fully furnished including a full kitchen, washer/dryer in the unit and private lanai. Currently in the Aqua-Aston hotel pool. Great on-site amenities to relax and enjoy Maui's resort lifestyle.

  Kay Mukaigawa Engel & Volkers Honolulu

  2575 S Kihei Rd Unit H101, Kihei, HI 96753
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  $749,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  2575 S Kihei Rd Unit H207, Kihei, HI 96753

  What a fantastic deal. This condo has been upgraded in 2023 with superior upgrades and professional decor. Must see to appreciate. 2 pools, 2 tennis courts, 2 BBQ areas, garage parking. 2 pets under 20#. Low maintenance fees and excellent location in South Kihei. Beach access in minutes, restaurants of all levels within walking and short drive distance. H2 zoning offering security of STR

  Kevin Eliason Maui Paradise Properties LLC

  2575 S Kihei Rd Unit H207, Kihei, HI 96753
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  $925,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2575 S Kihei Rd Unit G101, Kihei, HI 96753

  Steps from the sand and perfectly positioned in South Kihei, Maui Banyan G101 offers an easygoing island escape right across from the beach and within walking distance of restaurants, shops, and local favorites. This inviting ground-floor corner condo features 2 bedrooms, 2 bathrooms. The condo is Hotel Zoned and perfect for personal or vacation rental use with space for up to 6 guests, making it

  Daniel Kisiel Hawaii Real Estate Executives Inc

  2575 S Kihei Rd Unit G101, Kihei, HI 96753
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  $900,000

  $275K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  2575 S Kihei Rd Unit Q104, Kihei, HI 96753

  This South Kihei condo will check off most everything on your wish list! Welcome to Maui Banyan Q-104, a fully furnished first-floor 2 bed, 2 bath condo in this highly desirable, Hotel-Zoned community—perfect as a primary home, vacation retreat, or high-performing, legally permitted short-term rental (the complex is NOT on the Minatoya List). The flexible lock-off floor plan allows the unit to be

  Dennis O'Donnell Romvari Realty Ltd

  2575 S Kihei Rd Unit Q104, Kihei, HI 96753
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  $1,250,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2575 S Kihei Rd Unit P310, Kihei, HI 96753

  Live Life to the fullest in your new lovingly remodeled condo, with wonderful heated pools, jacuzzies, tennis court, and BBQ at the pool cabana area to enjoy. What an added advantage to be located directly across the road from one of the Best white sandy beaches in Kihei; Kamaole 2 Beach park, where you can do all the fun beach activities; kayak, stand up paddle or just soak up the sunshine. Also

  Marilyn Steinmetz AOK Properties LLC

  2575 S Kihei Rd Unit P310, Kihei, HI 96753
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  $18,900,000

  $1M PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,834 Sq Ft

  5417 Makena Rd Unit 2, Kihei, HI 96753

  Experience the best of South Maui living in this exclusive Makena Sunset residence, ideally located directly across from Maluaka Beach, Makena, Maui. Enter through a private gated entry to one of only four homes in this intimate and highly sought-after neighborhood. Enjoy the ultimate island lifestyle with the beach just steps away for snorkeling, swimming, and sunsets. This spacious home

  Robert Merriman Discovery Makena Realty LLC

  5417 Makena Rd Unit 2, Kihei, HI 96753
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  $1,150,000

  $49K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  2575 S Kihei Rd Unit T207, Kihei, HI 96753

  Beautifully remodeled 2-bed, 2-bath hotel zoned condo located in the desirable Maui Banyan, directly across the street from the world-famous Kamaole II Beach Park. This south-facing second-floor unit enjoys added privacy with lush palm views from the lanai and cooling island breezes. The interior features a modern, ocean-inspired design with updated cabinetry, sleek finishes, and a stunning

  Jeanne Dunn Corcoran Pacific Properties

  2575 S Kihei Rd Unit T207, Kihei, HI 96753
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  /19

  $29,900,000

  $9M PRICE DROP

  • 5 Beds
  • 6 Baths
  • 9,176 Sq Ft

  5050 Makena Rd, Kihei, HI 96753

  Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living.

  Robert Merriman Discovery Makena Realty LLC

  5050 Makena Rd, Kihei, HI 96753
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  $2,749,000

  • 2 Beds
  • 3 Baths
  • 2,183 Sq Ft

  4955 Makena Rd Unit F102, Kihei, HI 96753

  Welcome to Na Hale O Makena, one of South Maui’s most private and low-density luxury communities. This beautifully appointed 2-bedroom, 2.5-bath residence offers the ease and comfort of desirable ground-level living with no stairs/elevators to enter, creating effortless access throughout the home and lanai. Tucked within lush tropical landscaping, the property enjoys an exceptional sense of

  Max Blair Coldwell Banker Island Prop(S)

  4955 Makena Rd Unit F102, Kihei, HI 96753
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  $620,000

  $145K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  2575 S Kihei Rd Unit H210, Kihei, HI 96753

  Welcome to Maui Banyan H-210, a beautifully maintained 1-bedroom, 2-bathroom condo located in one of Kihei's most sought-after resort communities. One of the advantages of owning at Maui Banyan is that this property is HOTEL ZONED. This designation provides peace of mind for owners, as it ensures greater flexibility for vacation rentals and is NOT impacted by Bill 9, yet the pricing is comparable

  Malia Miller Coldwell Banker Island Prop-Ku

  2575 S Kihei Rd Unit H210, Kihei, HI 96753

Showing Results 161 - 188, Page 5 of 5