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. $278 to $341/night

    Junior Suite Oceanfront #706

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $278 to $341/night

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $1,276 to $2,900/night

    Ka'ulu Villa 129B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  7. $1,224 to $1,698/night

    Kaanapali Alii 456

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $303 to $754/night

    Kaanapali Plantation #28

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
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  11. $203 to $464/night

    Kaanapali Plantation #52

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  13. $219 to $510/night

    Kaanapali Plantation #57

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  15. $183 to $718/night

    Kaanapali Royal #A201 (MAUI)

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $267 to $679/night

    Kaanapali Royal #A303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  19. $269 to $534/night

    Kaanapali Royal #C101

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  21. $209 to $551/night

    Kaanapali Royal #E302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  23. $269 to $580/night

    Kaanapali Royal #H302

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $293 to $545/night

    Kaanapali Royal #N302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  27. $247 to $534/night

    Kaanapali Royal #P101

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
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  29. $247 to $447/night

    Kaanapali Royal #P102

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $349 to $664/night

    Kaanapali Royal B303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $376 to $688/night

    Kaanapali Royal C202

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $381 to $679/night

    Kaanapali Royal E101

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $375 to $688/night

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $369 to $668/night

    Kaanapali Royal H303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $398 to $919/night

    Kaanapali Royal N102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $405 to $666/night

    Kaanapali Royal Q101

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $357 to $731/night

    Kaanapali Shores #159

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $407 to $800/night

    Kaanapali Shores #160

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $348 to $783/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $319 to $684/night

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $406 to $706/night

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $550 to $935/night

    Kaanapali Shores 103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $563 to $1,044/night

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $256 to $393/night

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $526 to $949/night

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $409 to $864/night

    Kaanapali Shores 527

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $279 to $528/night

    Kaanapali Shores 546

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $439 to $859/night

    Kaanapali Shores 613

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $253 to $516/night

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $485 to $920/night

    Kaanapali Shores 725

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $309 to $654/night

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $316 to $504/night

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $273 to $505/night

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $279 to $579/night

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $344 to $550/night

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $193 to $359/night

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $193 to $359/night

    Kaanapali Shores Studio 742

    Studio BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $482 to $839/night

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $348 to $696/night

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $291/night

    Kahaluu Bay Villas #304

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $309 to $545/night

    Kahana Manor 410

    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. $899/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $464 to $1,583/night

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $501 to $969/night

    Kahana Outrigger #4B2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $203 to $584/night

    Kahana Reef 103

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $265 to $490/night

    Kahana Reef 107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $296 to $510/night

    Kahana Reef 111

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $211 to $638/night

    Kahana Reef 117

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $240 to $670/night

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $235 to $405/night

    Kahana Reef 303

    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. $326 to $383/night

    Kahana Sunset A3

    2 Bedrooms2.5 BathroomsSleeps 4
    4 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $428 to $484/night

    Kahana Sunset A4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $428 to $484/night

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $253 to $366/night

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $214 to $298/night

    Kahana Sunset B1B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $276 to $366/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $186 to $214/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $309 to $394/night

    Kahana Sunset B6

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pool
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $309 to $394/night

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $251 to $406/night

    Kahana Sunset C 3

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $363 to $586/night

    Kahana Sunset C1

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $219 to $276/night

    Kahana Sunset C4

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $276 to $332/night

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $276 to $332/night

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $253 to $309/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $276 to $332/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $276 to $332/night

    Kahana Sunset D6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $276 to $332/night

    Kahana Sunset D7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $276 to $332/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $276 to $332/night

    Kahana Sunset D9

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $239 to $394/night

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $355 to $536/night

    Kahana Sunset E4

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $356 to $540/night

    Kahana Sunset E5

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $276 to $332/night

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $276 to $332/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    14 nights minstay
    Pool
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $428 to $484/night

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $428 to $484/night

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $428 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $371 to $484/night

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $388 to $968/night

    Kahana Villa E601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $233 to $338/night

    Kahana Villa F406 1Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $267 to $789/night

    Kahana Villas #F507

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $378 to $605/night

    Kahana Villas F401

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $164 to $406/night

    Kahikole

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $811 to $2,079/night

    Kahikolu

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $907 to $2,016/night

    Kai Halulu

    3 Bedrooms3.5 BathroomsSleeps 7
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $426 to $788/night

    Kai Vista

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $1,701 to $2,520/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $7,860 to $12,620/night

    Kailua Shores Estate 8 Bedroom

    8 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $567 to $756/night

    KAINALU HANALEI

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $350/night

    Kalani Kai 105

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $110 to $303/night

    Kalanikai 306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $211 to $348/night

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations