FEATURED WAILEA, SOUTH MAUI STAYS

Vacation Rentals in Wailea, South Maui

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Showing 73 of 73 properties

  1. Wailea
    Palms at Wailea 303

    CONDOMINIUM

    Palms at Wailea 303

    Multiple Units

    Wailea, HI, Palms at Wailea 303 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  2. Wailea
    Grand Champions 139

    CONDOMINIUM

    Grand Champions 139

    Multiple Units

    Wailea, HI, Grand Champions 139 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  3. Wailea
    Wailea Beach Villa H102

    VILLA

    Wailea Beach Villa H102

    Multiple Units

    Wailea, HI, Wailea Beach Villa H102 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  4. Wailea
    Wailea Ekahi 25A

    CONDOMINIUM

    Wailea Ekahi 25A

    Multiple Units

    Wailea, HI, Wailea Ekahi 25A vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  5. Wailea
    Wailea Beach Villa I204

    VILLA

    Wailea Beach Villa I204

    Multiple Units

    Wailea, HI, Wailea Beach Villa I204 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  6. Wailea
    Palms at Wailea 1501

    CONDOMINIUM

    Palms at Wailea 1501

    1 Bedroom 2 Bathrooms 4 Guests

    Wailea, HI, Palms at Wailea 1501 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  7. Wailea
    Palms at Wailea 206

    CONDOMINIUM

    Palms at Wailea 206

    Multiple Units

    Wailea, HI, Palms at Wailea 206 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  8. Wailea
    Wailea Ekahi 45A

    CONDOMINIUM

    Wailea Ekahi 45A

    Multiple Units

    Wailea, HI, Wailea Ekahi 45A vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  9. Wailea
    Hoolei 24-6

    VILLA

    Hoolei 24-6

    Multiple Units

    Wailea, HI, Hoolei 24-6 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  10. Wailea
    Hoolei 112-5

    VILLA

    Hoolei 112-5

    Multiple Units

    Wailea, HI, Hoolei 112-5 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  11. Wailea
    Wailea Ekahi 36B

    CONDOMINIUM

    Wailea Ekahi 36B

    Multiple Units

    Wailea, HI, Wailea Ekahi 36B vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  12. Wailea
    Wailea Elua 2109

    CONDOMINIUM

    Wailea Elua 2109

    Multiple Units

    Wailea, HI, Wailea Elua 2109 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  13. Wailea
    Grand Champions 74

    CONDOMINIUM

    Grand Champions 74

    Multiple Units

    Wailea, HI, Grand Champions 74 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  14. Wailea
    Hoolei 24-4

    VILLA

    Hoolei 24-4

    Multiple Units

    Wailea, HI, Hoolei 24-4 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  15. Wailea
    Grand Champions 68

    CONDOMINIUM

    Grand Champions 68

    Multiple Units

    Wailea, HI, Grand Champions 68 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  16. Wailea
    Hoolei 55-3

    VILLA

    Hoolei 55-3

    Multiple Units

    Wailea, HI, Hoolei 55-3 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  17. Wailea
    Palms at Wailea 2104

    CONDOMINIUM

    Palms at Wailea 2104

    2 Bedrooms 2 Bathrooms 4 Guests

    Wailea, HI, Palms at Wailea 2104 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  18. Wailea
    Grand Champions 35

    CONDOMINIUM

    Grand Champions 35

    2 Bedrooms 2 Bathrooms 5 Guests

    Wailea, HI, Grand Champions 35 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  19. Wailea
    Wailea Ekahi 17E

    CONDOMINIUM

    Wailea Ekahi 17E

    1 Bedroom 2 Bathrooms 2 Guests

    Wailea, HI, Wailea Ekahi 17E vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  20. Wailea
    Hoolei 39-3

    TOWNHOUSE

    Hoolei 39-3

    Multiple Units

    Wailea, HI, Hoolei 39-3 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  21. Wailea
    Wailea Elua 2303

    CONDOMINIUM

    Wailea Elua 2303

    Multiple Units

    Wailea, HI, Wailea Elua 2303 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  22. Wailea
    Wailea Ekahi 34B

    CONDOMINIUM

    Wailea Ekahi 34B

    Multiple Units

    Wailea, HI, Wailea Ekahi 34B vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  23. Wailea
    Makena Surf F201

    CONDOMINIUM

    Makena Surf F201

    Multiple Units

    Wailea, HI, Makena Surf F201 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  24. Wailea
    Hoolei 17-3

    VILLA

    Hoolei 17-3

    Multiple Units

    Wailea, HI, Hoolei 17-3 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  25. Wailea
    Grand Champions 145

    CONDOMINIUM

    Grand Champions 145

    Multiple Units

    Wailea, HI, Grand Champions 145 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  26. Wailea
    Grand Champions 130

    CONDOMINIUM

    Grand Champions 130

    2 Bedrooms 2 Bathrooms 6 Guests

    Wailea, HI, Grand Champions 130 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  27. Wailea
    Wailea Ekolu 904

    CONDOMINIUM

    Wailea Ekolu 904

    Multiple Units

    Wailea, HI, Wailea Ekolu 904 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  28. Wailea
    Wailea Ekahi 48A

    CONDOMINIUM

    Wailea Ekahi 48A

    Multiple Units

    Wailea, HI, Wailea Ekahi 48A vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  29. Wailea
    Wailea Beach Villa B102

    VILLA

    Wailea Beach Villa B102

    Multiple Units

    Wailea, HI, Wailea Beach Villa B102 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  30. Wailea
    Wailea Ekahi 53D

    CONDOMINIUM

    Wailea Ekahi 53D

    Multiple Units

    Wailea, HI, Wailea Ekahi 53D vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  31. Wailea
    Hoolei 55-2

    TOWNHOUSE

    Hoolei 55-2

    Multiple Units

    Wailea, HI, Hoolei 55-2 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  32. Wailea
    Wailea Ekolu 208

    CONDOMINIUM

    Wailea Ekolu 208

    Multiple Units

    Wailea, HI, Wailea Ekolu 208 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  33. Wailea
    Hoolei 17-1

    TOWNHOUSE

    Hoolei 17-1

    Multiple Units

    Wailea, HI, Hoolei 17-1 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  34. Wailea
    Wailea Beach Villa H202

    VILLA

    Wailea Beach Villa H202

    Multiple Units

    Wailea, HI, Wailea Beach Villa H202 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  35. Wailea
    Makena Surf B305

    CONDOMINIUM

    Makena Surf B305

    Multiple Units

    Wailea, HI, Makena Surf B305 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  36. Wailea
    Wailea Ekahi 5E

    CONDOMINIUM

    Wailea Ekahi 5E

    Multiple Units

    Wailea, HI, Wailea Ekahi 5E vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  37. Wailea
    Grand Champions 36

    CONDOMINIUM

    Grand Champions 36

    Multiple Units

    Wailea, HI, Grand Champions 36 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  38. Wailea
    Wailea Ekolu 104

    CONDOMINIUM

    Wailea Ekolu 104

    2 Bedrooms 2 Bathrooms 6 Guests

    Wailea, HI, Wailea Ekolu 104 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  39. Wailea
    Hoolei 24-1

    VILLA

    Hoolei 24-1

    Multiple Units

    Wailea, HI, Hoolei 24-1 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  40. Wailea
    Palms at Wailea 403

    CONDOMINIUM

    Palms at Wailea 403

    Multiple Units

    Wailea, HI, Palms at Wailea 403 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  41. Wailea
    Palms at Wailea 601

    CONDOMINIUM

    Palms at Wailea 601

    Multiple Units

    Wailea, HI, Palms at Wailea 601 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  42. Wailea
    Grand Champions 60

    CONDOMINIUM

    Grand Champions 60

    Multiple Units

    Wailea, HI, Grand Champions 60 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  43. Wailea
    Wailea Ekolu 804

    CONDOMINIUM

    Wailea Ekolu 804

    1 Bedroom 2 Bathrooms 4 Guests

    Wailea, HI, Wailea Ekolu 804 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  44. Wailea
    Grand Champions 170

    CONDOMINIUM

    Grand Champions 170

    Multiple Units

    Wailea, HI, Grand Champions 170 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  45. Wailea
    Wailea Elua 2305

    CONDOMINIUM

    Wailea Elua 2305

    Multiple Units

    Wailea, HI, Wailea Elua 2305 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  46. Wailea
    Palms at Wailea 609

    CONDOMINIUM

    Palms at Wailea 609

    Multiple Units

    Wailea, HI, Palms at Wailea 609 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  47. Wailea
    Grand Champions 30

    CONDOMINIUM

    Grand Champions 30

    2 Bedrooms 2 Bathrooms 7 Guests

    Wailea, HI, Grand Champions 30 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  48. Wailea
    Wailea Ekahi 49F

    CONDOMINIUM

    Wailea Ekahi 49F

    Multiple Units

    Wailea, HI, Wailea Ekahi 49F vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  49. Wailea
    Grand Champions 29

    CONDOMINIUM

    Grand Champions 29

    1 Bedroom 1 Bathroom 2 Guests

    Wailea, HI, Grand Champions 29 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  50. Wailea
    Grand Champions 141

    CONDOMINIUM

    Grand Champions 141

    Multiple Units

    Wailea, HI, Grand Champions 141 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  51. Wailea
    Hoolei 24-2

    VILLA

    Hoolei 24-2

    Multiple Units

    Wailea, HI, Hoolei 24-2 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  52. Wailea
    Polo Beach Club 107

    CONDOMINIUM

    Polo Beach Club 107

    Multiple Units

    Wailea, HI, Polo Beach Club 107 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  53. Wailea
    Wailea Beach Villa I503

    VILLA

    Wailea Beach Villa I503

    Multiple Units

    Wailea, HI, Wailea Beach Villa I503 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  54. Wailea
    Wailea Ekolu 908

    CONDOMINIUM

    Wailea Ekolu 908

    Multiple Units

    Wailea, HI, Wailea Ekolu 908 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  55. Wailea
    Grand Champions 137

    CONDOMINIUM

    Grand Champions 137

    Multiple Units

    Wailea, HI, Grand Champions 137 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  56. Wailea
    Grand Champions 40

    CONDOMINIUM

    Grand Champions 40

    2 Bedrooms 2 Bathrooms 4 Guests

    Wailea, HI, Grand Champions 40 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  57. Wailea
    Grand Champions 122

    CONDOMINIUM

    Grand Champions 122

    Multiple Units

    Wailea, HI, Grand Champions 122 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  58. Wailea
    Wailea Ekahi 36E

    CONDOMINIUM

    Wailea Ekahi 36E

    Multiple Units

    Wailea, HI, Wailea Ekahi 36E vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  59. Wailea
    Wailea Ekahi 26A

    CONDOMINIUM

    Wailea Ekahi 26A

    Multiple Units

    Wailea, HI, Wailea Ekahi 26A vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  60. Wailea
    Wailea Ekolu 502

    CONDOMINIUM

    Wailea Ekolu 502

    Multiple Units

    Wailea, HI, Wailea Ekolu 502 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  61. Wailea
    Wailea Ekolu 1405

    CONDOMINIUM

    Wailea Ekolu 1405

    Multiple Units

    Wailea, HI, Wailea Ekolu 1405 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  62. Wailea
    Palms at Wailea 1904

    CONDOMINIUM

    Palms at Wailea 1904

    Multiple Units

    Wailea, HI, Palms at Wailea 1904 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  63. Wailea
    Polo Beach Club 703

    CONDOMINIUM

    Polo Beach Club 703

    2 Bedrooms 2 Bathrooms 4 Guests

    Wailea, HI, Polo Beach Club 703 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  64. Wailea
    Wailea Ekolu 1510

    CONDOMINIUM

    Wailea Ekolu 1510

    Multiple Units

    Wailea, HI, Wailea Ekolu 1510 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  65. Wailea
    Grand Champions 136

    CONDOMINIUM

    Grand Champions 136

    Multiple Units

    Wailea, HI, Grand Champions 136 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  66. Wailea
    Hoolei 12-4

    VILLA

    Hoolei 12-4

    Multiple Units

    Wailea, HI, Hoolei 12-4 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  67. Wailea
    Wailea Ekolu 1603

    CONDOMINIUM

    Wailea Ekolu 1603

    2 Bedrooms 2 Bathrooms 4 Guests

    Wailea, HI, Wailea Ekolu 1603 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  68. Wailea
    Wailea Beach Villa B202

    VILLA

    Wailea Beach Villa B202

    3 Bedrooms 3.5 Bathrooms 8 Guests

    Wailea, HI, Wailea Beach Villa B202 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  69. Wailea
    Polo Beach Club 106

    CONDOMINIUM

    Polo Beach Club 106

    2 Bedrooms 2 Bathrooms 6 Guests

    Wailea, HI, Polo Beach Club 106 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  70. Wailea
    Hoolei 21-3

    TOWNHOUSE

    Hoolei 21-3

    Multiple Units

    Wailea, HI, Hoolei 21-3 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  71. Wailea
    Wailea Beach Villa M312

    VILLA

    Wailea Beach Villa M312

    3 Bedrooms 3 Bathrooms 8 Guests

    Wailea, HI, Wailea Beach Villa M312 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  72. Wailea
    Wailea Ekahi 40D

    CONDOMINIUM

    Wailea Ekahi 40D

    1 Bedroom 2 Bathrooms 4 Guests

    Wailea, HI, Wailea Ekahi 40D vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  73. Wailea
    Wailea Ekahi 37E

    CONDOMINIUM

    Wailea Ekahi 37E

    1 Bedroom 2 Bathrooms 5 Guests

    Wailea, HI, Wailea Ekahi 37E vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now