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  1. $224 to $850/night

    Grand Champions 141

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $289 to $872/night

    Sugar Beach Resort 113

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $1,096 to $4,770/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $362 to $572/night

    Waipouli Beach Resort C-105

    2 Bedrooms, 3 Bathrooms, Sleeps 4
    3 nights minstay
    Pool Hot Tub
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  9. $362 to $541/night

    Waipouli Beach Resort E-205

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool Hot Tub
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  11. $197 to $524/night

    Kamaole Sands 6-103

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $231 to $872/night

    Grand Champions 122

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $328 to $467/night

    Regency at Poipu Kai #914

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 nights minstay
    Pool Hot Tub
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  17. $467 to $677/night

    Waipouli Beach Resort G-306

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool Hot Tub
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  19. $467 to $677/night

    Waipouli Beach Resort G-306

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool Hot Tub
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  21. $214 to $580/night

    Sugar Beach Resort PH8

    Multiple Units Available
    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. $196 to $685/night

    Grand Champions 136

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $865 to $3,362/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $2,670 to $9,559/night

    Wailea Beach Villa B202

    3 Bedrooms, 3.5 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $258 to $635/night

    Kamaole Sands 7-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $3,035 to $10,816/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $1,038 to $3,624/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $265 to $1,042/night

    Grand Champions 60

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $250 to $620/night

    Kamaole Sands 6-104

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $923 to $3,810/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $254 to $688/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $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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  47. $329 to $1,660/night

    Grand Champions 170

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $467 to $677/night

    Waipouli Beach Resort G-404

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool Hot Tub
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  51. $467 to $677/night

    Waipouli Beach Resort G-404

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool Hot Tub
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  53. $268 to $1,007/night

    Grand Champions 36

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $283 to $1,024/night

    Grand Champions 138

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  57. $1,141 to $4,247/night

    The Cove Hale

    4 Bedrooms, 4 Bathrooms, Sleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  59. $174 to $571/night

    Kamaole Sands 8-101

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

  61. $987 to $4,224/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $808 to $2,779/night

    Wailea Beach Villa J106

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

  65. $921 to $3,716/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  67. $980 to $4,984/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  69. $362 to $572/night

    Waipouli Beach Resort C-205

    2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 nights minstay
    Pool Hot Tub
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  71. $520 to $1,915/night

    Wailea Elua 2303

    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

  73. $204 to $510/night

    Kamaole Sands 8-206

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  75. $231 to $894/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  77. $272 to $738/night

    Sugar Beach Resort 409

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  79. $288 to $833/night

    Sugar Beach Resort 235

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

  81. $186 to $575/night

    Kamaole Sands 9-310

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

  83. $2,532 to $9,183/night

    Andaz Villa 810

    3 Bedrooms, 4 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  85. $520 to $3,339/night

    Wailea Beach Villa I204

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

  87. $923 to $3,422/night

    Ho'olei 55-3

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

  89. $231 to $656/night

    Kamaole Sands 5-211

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

  91. $243 to $784/night

    Grand Champions 68

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

  93. $923 to $4,151/night

    Ho'olei 24-4

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

  95. $243 to $1,102/night

    Grand Champions 139

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

  97. $866 to $3,406/night

    Ho'olei 24-6

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

  99. $213 to $772/night

    Grand Champions 74

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

  101. $767 to $2,779/night

    Wailea Beach Villa H102

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

  103. $168 to $510/night

    Kamaole Sands 4-208

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

  105. $1,038 to $4,041/night

    Ho'olei 112-5

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

  107. $320 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom, 1.5  Bathroom, Sleeps 4
    2 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  109. $204 to $973/night

    Grand Champions 67

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  111. $716 to $1,981/night

    Wailea Elua 2109

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

  113. $243 to $1,002/night

    Kamaole Sands 7-410

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

  115. $220 to $624/night

    Kamaole Sands 6-102

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