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  1. $802 to $3,535/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $224 to $850/night

    Grand Champions 141

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $345 to $1,277/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $231 to $871/night

    Grand Champions 122

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $196 to $685/night

    Grand Champions 136

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $865 to $3,563/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $260 to $1,092/night

    Menehune Shores 112

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $346 to $1,120/night

    Grand Champions 40

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $289 to $942/night

    Grand Champions 29

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $923 to $2,559/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $2,811 to $9,598/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $981 to $4,044/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $231 to $897/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $921 to $3,928/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $980 to $4,984/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $268 to $1,007/night

    Grand Champions 36

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $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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  35. $265 to $1,042/night

    Grand Champions 60

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $329 to $1,660/night

    Grand Champions 170

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $923 to $3,810/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $281 to $1,220/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $375 to $1,179/night

    Grand Champions 30

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $283 to $1,028/night

    Grand Champions 138

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $987 to $4,224/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $243 to $1,167/night

    Grand Champions 139

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  51. $273 to $1,120/night

    Grand Champions 35

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $866 to $3,600/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $204 to $978/night

    Grand Champions 67

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  57. $213 to $814/night

    Grand Champions 74

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  59. $243 to $784/night

    Grand Champions 68

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  61. $289 to $737/night

    Kihei Ali'i Kai B108

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $220 to $624/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  65. $2,532 to $9,183/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  67. $186 to $597/night

    Kamaole Sands 6-207

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  69. $923 to $3,422/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  71. $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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  73. $433 to $1,284/night

    Palms at Wailea 2104

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  75. $923 to $4,151/night

    Ho'olei 24-4

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