Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. $624 to $749/night

    Puamana 52-3

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $300 to $438/night

    Hale Ono Loa 102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $413 to $503/night

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  7. $278 to $341/night

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $278 to $640/night

    Lokelani #C205

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $186 to $459/night

    Papakea #A105

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  13. $220 to $532/night

    Hololani #B-403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  15. $191 to $636/night

    Maui Ka'anapali Villas Studio Premier Condo A417

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $232 to $661/night

    Valley Isle #1209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  19. $290 to $619/night

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $325 to $638/night

    Mahana Resort #1106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $203 to $383/night

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $369 to $744/night

    Kapalua Golf Villa 23V3 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $261 to $853/night

    Lahaina Shores #425

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $524 to $658/night

    Eldorado K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $220 to $532/night

    Hololani #B-802

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  33. $180 to $510/night

    Papakea #D304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  35. $191 to $408/night

    Lokelani #C104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  37. $253 to $366/night

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $349 to $585/night

    A5-2 Beachfront Loft Suite

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $150 to $583/night

    Ilikai Tower 2136

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $333 to $443/night

    Paki Maui 415

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $260/night

    Turtle Bay Sunset Retreat***TA-188332646401 Available 30...

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $297/night

    171

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $304 to $467/night

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $209 to $354/night

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $139 to $307/night

    Valley Isle #107

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $225 to $820/night

    Kona Nalu #302

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $205 to $724/night

    Kona Bali Kai #206- 2 Bedroom

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $556 to $1,094/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $288 to $494/night

    Kapalua Bay Villa 12G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $264 to $598/night

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $513 to $1,668/night

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $571 to $1,668/night

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $145 to $441/night

    Ilikai Tower 735

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $294 to $494/night

    Kapalua Ridge Villa 114 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $428 to $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $248 to $366/night

    Bay Villa 30G1

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $276 to $332/night

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $156 to $330/night

    Valley Isle #1106

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $306 to $394/night

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $319 to $574/night

    Mahana Resort #804

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $302 to $669/night

    Lahaina Shores #501

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $128 to $332/night

    Paki Maui #420

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $210 to $530/night

    Ali'i Kai 7204

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $419 to $898/night

    Poipu Shores B202

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $463 to $630/night

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $490 to $544/night

    Maui Banyan Q204

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $294 to $494/night

    Kapalua Golf Villa 25V2 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $196 to $284/night

    Unit 106

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $363/night

    249

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $344 to $744/night

    Kapalua Golf Villa 15P78 Gold

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $237/night

    Turtle Bay Hale Kai***NUC90-TVU-0746 Available for 2 peo...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $481 to $906/night

    Kapalua Ridge Villa 1214 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $152 to $219/night

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $276 to $332/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $138 to $500/night

    Ilikai Marina 1094

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $261 to $619/night

    Papakea #E401

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $273 to $696/night

    Lahaina Shores #531

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $257 to $361/night

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $549/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $584/night

    Sea Village 4-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $405 to $486/night

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $428 to $484/night

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $397 to $1,204/night

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $408 to $456/night

    Eldorado G205

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $271 to $431/night

    Valley Isle 204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $365 to $483/night

    Kapalua Ridge Villa #1521

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $284 to $438/night

    Hale Ono Loa 402

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $152 to $219/night

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $276 to $332/night

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $350/night

    Kalani Kai 105

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $781 to $1,281/night

    Kapalua Bay Villa 34B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $428 to $484/night

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $283/night

    Turtle Bay Bird of Paradise**TA-086947840001 Available 3...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $466 to $1,384/night

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $452/night

    Keauhou Kona Surf & Racquet Club #3-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $294/night

    Kona Isle B31

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $202 to $636/night

    Aina Nalu Condo D201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $332 to $834/night

    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $418 to $630/night

    Kahana Sunset C1

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $281 to $494/night

    Kapalua Golf Villa 11T4 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $122 to $394/night

    Royal Kahana #319

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $313 to $606/night

    Mahana Resort #1017

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $503 to $761/night

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $450 to $586/night

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $296 to $416/night

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $813 to $1,313/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $294 to $563/night

    Kapalua Golf Villa 25T4 Gold Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $224 to $249/night

    WB1909 Waikiki Steps to the Beach Wifi Ocean View RFRF-C...

    1 Bedroom BathroomSleeps 5
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $199 to $502/night

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $397 to $1,204/night

    Hale Lau Wai Ko Olina Beach Villa (O704)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $266/night

    Turtle Bay Deep Blue**NUC 90-TVU-0523

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $251/night

    Waikiki Beach Walk 2 Bedroom

    Multiple Units Available
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $158 to $286/night

    Mountain & Golf Course Views! 3 Bed/3 Bath

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $1,255 to $1,313/night

    Alii Point

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations