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  1. $3,035 to $11,599/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,038 to $5,001/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $981 to $4,337/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $923 to $4,451/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $923 to $3,670/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $866 to $3,860/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $865 to $3,810/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $848 to $1,916/night

    Hale Ohana Nui

    5 Bedrooms6.5 BathroomsSleeps 12
    3 nights minstay
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  27. $802 to $3,792/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $767 to $2,974/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $716 to $2,130/night

    Wailea Elua 2109

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $701 to $3,465/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $549 to $1,916/night

    Big Island Kona Reef D-22

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $469 to $1,789/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $467 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $467 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $458 to $1,608/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  55. $441 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $436 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $436 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $396 to $1,718/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $388 to $572/night

    Puu Poa #305

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $388 to $457/night

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $362 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $362 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $362 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $362 to $467/night

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $357 to $1,586/night

    Wailea Ekolu 908

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  77. $352 to $457/night

    Kaha Lani #222

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $346 to $1,094/night

    Kauai Regency at Poipu Kai #313

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $345 to $1,362/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  83. $331 to $415/night

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $331 to $415/night

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $331 to $415/night

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $331 to $415/night

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $324 to $993/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $320 to $493/night

    Pali Ke Kua #241

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $320 to $493/night

    Pali Ke Kua #241

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $318 to $1,340/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  99. $315 to $630/night

    Keauhou Kona Surf & Racquet Club #5-104

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $306 to $1,324/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $300 to $1,243/night

    Wailea Ekahi 45A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $289 to $970/night

    Wailea Ekahi 36B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $289 to $980/night

    Wailea Ekahi 49F

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $283 to $1,146/night

    Nohonani 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $282 to $1,592/night

    Wailea Ekolu 502

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $281 to $1,306/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $279 to $1,295/night

    Wailea Ekolu 1705

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $273 to $1,198/night

    Grand Champions 35

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $264 to $468/night

    KIHEI BEACH, #305*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $260 to $1,103/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $250 to $678/night

    Kamaole Sands 6-104

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $247 to $671/night

    Panoramic Ocean View 1BR Condo Suite 150 feet from the O...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $243 to $1,093/night

    Kamaole Sands 7-410

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $243 to $685/night

    Kahana Reef 120

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $231 to $959/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $224 to $909/night

    Grand Champions 141

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $224 to $876/night

    Kihei Garden Estates D104

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $220 to $681/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $213 to $740/night

    Hale Kamaole 121

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $208 to $541/night

    Hale Ono Loa 411

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $204 to $643/night

    Kihei Akahi C-507

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $203 to $249/night

    Hale Anuenue Nuku- The Rainbows End

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $192 to $541/night

    Kihei Akahi C-612

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $183 to $316/night

    Island Sands 110

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $172 to $496/night

    Kihei Akahi C-317

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $166 to $566/night

    Kihei Kai Nani #8-362

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $158 to $525/night

    Kona Pacific A206

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $141 to $461/night

    Hale Ohi'a Lehua

    3 BedroomsBathroomsSleeps 8
    1 night minstay
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $76 to $458/night

    Maluhia Kahakai

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations