RedAwning has over 350 Maui vacation homes and condos which all include instant online booking and no security deposits, to make your trip easy and stress-free. Maui is home to some of Hawaii’s most beautiful beaches and offers plenty of opportunities for adventure, from snorkeling with turtles to hiking through the bamboo forest to cliff diving in Hana. Book your stay today!

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  1. $304 to $338/night

    Whaler On Kaanapali 763

    Studio BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
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  3. $528 to $774/night

    Whaler at Kaanapali Beach #912

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $870 to $1,401/night

    Whaler at Kaanapali Beach #852

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $779 to $1,188/night

    Whaler at Kaanapali Beach #723

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $425 to $603/night

    Whaler at Kaanapali Beach #514

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $870 to $1,401/night

    Whaler at Kaanapali Beach #402

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $379 to $539/night

    Whaler at Kaanapali Beach #163

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $779 to $1,188/night

    Whaler at Kaanapali Beach #1173

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $696 to $829/night

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $261 to $542/night

    Whaler #656

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $3,248 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $546 to $581/night

    Wailea Ekolu 1606

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  25. $450 to $556/night

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  27. $214 to $1,056/night

    WAILEA EKOLU #203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  29. $375 to $500/night

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $360 to $469/night

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  33. $348 to $440/night

    Wailea Ekahi 36C

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  35. $302 to $393/night

    Valley Isle Resort #901 (MAUI)

    1 Bedroom0.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $304 to $481/night

    Valley Isle 902

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $249 to $348/night

    Valley Isle 407

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $481 to $538/night

    Valley Isle 204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  43. $241 to $311/night

    Valley Isle 110

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
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  45. $157 to $447/night

    Valley Isle #905

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  47. $186 to $522/night

    Valley Isle #809

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $209 to $638/night

    Valley Isle #808

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $139 to $406/night

    Valley Isle #806

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $145 to $273/night

    Valley Isle #707

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  55. $139 to $447/night

    Valley Isle #705

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $191 to $440/night

    Valley Isle #509

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $267 to $767/night

    Valley Isle #508

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $191 to $551/night

    Valley Isle #310

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $191 to $586/night

    Valley Isle #205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $232 to $580/night

    Valley Isle #1209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $157 to $441/night

    Valley Isle #1206

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $174 to $383/night

    Valley Isle #1204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $232 to $597/night

    Valley Isle #1203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $156 to $330/night

    Valley Isle #1106

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $173 to $375/night

    Valley Isle #1104

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $215 to $626/night

    Valley Isle #1103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $139 to $307/night

    Valley Isle #107

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $197 to $603/night

    Valley Isle #1004

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $302 to $354/night

    Unit 311

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $302 to $354/night

    Unit 310

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $365 to $429/night

    Unit 309

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $302 to $354/night

    Unit 305

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $302 to $354/night

    Unit 303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $249 to $302/night

    Unit 214

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $196 to $284/night

    Unit 213

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $196 to $284/night

    Unit 212

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $249 to $302/night

    Unit 209

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $196 to $284/night

    Unit 208

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $196 to $284/night

    Unit 207

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $196 to $284/night

    Unit 205

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $196 to $284/night

    Unit 204

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $196 to $284/night

    unit 203

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $249 to $302/night

    Unit 201

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $249 to $302/night

    Unit 114

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $196 to $284/night

    Unit 113

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $196 to $284/night

    Unit 111

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $196 to $284/night

    Unit 109

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $196 to $284/night

    Unit 108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $196 to $284/night

    Unit 106

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $196 to $284/night

    Unit 103

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $146 to $723/night

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $329 to $549/night

    The Plantation #1

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $116 to $335/night

    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $318 to $426/night

    Sugar Beach #618

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $334 to $444/night

    Sugar Beach #522

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $334 to $444/night

    Sugar Beach #520

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $334 to $444/night

    Sugar Beach #425

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $334 to $444/night

    Sugar Beach #416

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $334 to $444/night

    Sugar Beach #334

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $318 to $426/night

    Sugar Beach #326

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $334 to $444/night

    Sugar Beach #317

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $297 to $396/night

    Sugar Beach #302

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $297 to $396/night

    Sugar Beach #301

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $318 to $426/night

    Sugar Beach #227

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $318 to $426/night

    Sugar Beach #223

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $318 to $426/night

    Sugar Beach #133

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $334 to $444/night

    Sugar Beach #132

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $334 to $444/night

    Sugar Beach #127

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $334 to $444/night

    Sugar Beach #124

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $334 to $444/night

    Sugar Beach #120

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $334 to $444/night

    Sugar Beach #115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $426 to $611/night

    Spinnaker 216C

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $501 to $619/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $388 to $422/night

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $501 to $619/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $501 to $557/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $576 to $698/night

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $366 to $422/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $388 to $422/night

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $236 to $309/night

    Sands Of Kahana 318

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $591 to $689/night

    Sands of Kahana 316

    2 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $501 to $557/night

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $506 to $563/night

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $506 to $563/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $208 to $309/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $506 to $563/night

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $298 to $388/night

    Sands Of Kahana 134

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations