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Apartments for Rent in Wailea, HI with Pools

11 rentals available
  • 2 Bedroom 2 Bathroom Condo - Hawai‘i Charm Meets Modern Comfort in the Heart of South Kihei

    $3,200
    2619 South Kihei Road, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    2 bed
    Amenities

    Pool, Elevator, Clubhouse, Bbq/grill, Internet access, and Carpet

  • Makalii at Wailea 101 - 9A

    $6,998
    185 Holokahiki Lane, Wailea, HI 96753
    (808) 329-5300

    1 unit available
    3 bed
    Amenities

    In unit laundry, Dishwasher, Garage, Gym, Pool, Air conditioning + more

  • 2757 South Kihei RoadUnit 602

    $3,950
    2757 South Kihei Road, Wailea, HI 96753
    (808) 425-9997

    1 unit available
    2 bed
    Amenities

    In unit laundry, Dishwasher, Parking, Walk in closets, Pool, Air conditioning + more

  • Modern Elegancy at Makali'i in Wailea - Furnished 3 Bedrooms / 3 Bathrooms

    $7,500
    173 Holokahiki Lane, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    3 bed
    Amenities

    In unit laundry, Dishwasher, Garage, Stainless steel, Gym, Pool + more

  • Featured Unit 1
    Best market deals
    These units are the best deal in town.
  • Experience Elevated Island Living in Wailea – Expansive Golf Course and Ocean View Furnished Luxury Townhome

    $6,500
    3950 Kalai Waa Street, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    3 bed
    Amenities

    Granite counters, Parking, Recently renovated, Stainless steel, Gym, Pool + more

  • Kanani Wailea - Furnished 4 Bedroom 4.5 Bathrooms - World Class Amenities in Wailea Maui

    $9,000
    14 Poailani Place, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    4 bed
    Amenities

    On-site laundry, Pet friendly, Garage, Gym, Pool, Air conditioning + more

  • Modern Elegancy at Makali'i in Wailea on the edge of Makena - Furnished 3 Bedrooms / 3 Bathrooms

    $9,500
    161 Holomoana Way, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    3 bed
    Amenities

    In unit laundry, Patio / balcony, Dishwasher, Stainless steel, Gym, Pool + more

  • 2026 Kai Malu in Wailea? Nicely Furnished 3 bedroom 2.5 bathroom -Ocean Views and Fine Amenities Available 1/15/26 to 12/15/26

    $6,900
    156 Kainui Loop, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    3 bed
    Amenities

    Granite counters, Garage, Stainless steel, Gym, Pool, Air conditioning + more

  • Modern Elegancy at Makali'i in Wailea – Finely Furnished 3 Bedrooms / 3 Bathrooms

    $10,000
    137 Holomoana Way, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    3 bed
    Amenities

    In unit laundry, Dishwasher, Garage, Gym, Pool, Air conditioning + more

  • Modern Elegancy at Makali'i in Wailea on the boarder of Makena - Finely Furnished 2 Bedrooms / 2 Bathrooms

    $7,000
    172 Holomoana Way, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    2 bed
    Amenities

    In unit laundry, Dishwasher, Stainless steel, Gym, Pool, Air conditioning + more

  • Featured Unit 1
    Luxury apartments
    Top units for an elevated lifestyle.
  • Kihei Shores -Furnished 2bed/2bath - Underwater Artistry Condo - Complex Pool and Jacuzzi

    $4,000
    2747 S Kihei Rd, Wailea, HI 96753
    (808) 875-8988

    1 unit available
    2 bed
    Amenities

    In unit laundry, Dishwasher, Parking, Recently renovated, Stainless steel, Pool + more

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Frequently Asked Questions

City Guide for Wailea, HI

Wailea Beach earned the moniker of "America's Best Beach" in 1999. Take that, Florida!

Located on Maui's southern coast, the community of Wailea is known primarily as a vacation destination for those seeking sun, sand and surf. It's a resort area that offers amenities like restaurants, shopping, championship golf courses and acres of beach. Wailea's coastline is especially attractive; so attractive, in fact, that in 1999 Stephen P. Leatherman, a professor at Florida International University whose interest in coastal areas has earned him the nickname "Dr. Beach," used criteria like sand softness and water temperature to declare that Wailea had "America's Best Beach." (Since then, other shorelines have taken over the "best beach" crown, but it's a safe bet that Wailea's coastal area remains just as desirable as it was in the days of Pokemon and Y2K). View Wailea City Guide