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  1. $414 to $1,185/night

    Palms at Wailea 206

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $279 to $1,210/night

    Wailea Ekolu 1705

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $414 to $1,185/night

    Palms at Wailea 303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $923 to $3,422/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $1,038 to $4,041/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $433 to $1,284/night

    Palms at Wailea 2104

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $923 to $4,151/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $300 to $1,163/night

    Wailea Ekahi 45A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  17. $866 to $3,600/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $273 to $1,120/night

    Grand Champions 35

    2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $716 to $1,989/night

    Wailea Elua 2109

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $802 to $3,535/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $224 to $850/night

    Grand Champions 141

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $656 to $2,791/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $282 to $1,486/night

    Wailea Ekolu 502

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  31. $357 to $1,481/night

    Wailea Ekolu 908

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  33. $289 to $917/night

    Wailea Ekahi 49F

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  35. $981 to $4,044/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $345 to $1,273/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $865 to $3,553/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $668 to $2,499/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  43. $701 to $3,238/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  45. $396 to $1,609/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  47. $1,038 to $4,675/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $923 to $3,810/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  51. $281 to $1,220/night

    Grand Champions 130

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $3,035 to $10,816/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  55. $414 to $1,185/night

    Palms at Wailea 403

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  57. $324 to $877/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $231 to $897/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  61. $306 to $1,238/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $921 to $3,928/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  65. $469 to $1,671/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  67. $318 to $1,251/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  69. $260 to $1,035/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  71. $980 to $4,984/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
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