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. $398 to $480/night

    Kamaole Sands #08-411

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $344 to $460/night

    Kihei Surfside #210

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  5. $257 to $474/night

    MAALAEA SURF, #C-8

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
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  7. $464 to $806/night

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
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  9. $276 to $332/night

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  11. $281 to $334/night

    Maui Parkshore #303

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  13. $634 to $814/night

    WAILEA ELUA, #1309

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
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  15. $276 to $332/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  17. $366 to $422/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
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  19. $176 to $384/night

    Kaleialoha #207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $117 to $384/night

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  23. $159 to $384/night

    Kaleialoha #115

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $176 to $620/night

    HOL 119

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  27. $117 to $384/night

    Kaleialoha #214

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $868 to $1,120/night

    Hanalei Beach House: Steps to Surfing and Pier

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $619 to $1,156/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $427/night

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $321 to $390/night

    Kihei Akahi #D-615 (7th Flr)

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
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  37. $540 to $613/night

    Kamaole Sands #10-417

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $239 to $296/night

    Kauhale Makai #122

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $278 to $341/night

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $196 to $297/night

    Papakea E306

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $525/night

    Keauhou Kona Surf & Racket Club Townhouse #4

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $350/night

    Keauhou Kona Surf & Racquet Club#37

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $350/night

    Keauhou Kona Surf & Racquet Club #176

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  51. $350/night

    Banyan Tree 404D

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $350/night

    Kona Pacific B511

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $384/night

    Keauhou Kona Surf & Racquet Townhouse #36

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $204/night

    Keauhou Punahele E-102

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $584/night

    Sea Village 4-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $467/night

    Kona Makai 1-204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $239/night

    Kona Isle B31

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $467/night

    Royal Sea Cliff #704

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $326/night

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $467/night

    Kona Makai 2-201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $478/night

    Keauhou Kona Surf & Racquet Club#8-304

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $664/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 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. $253 to $382/night

    KAMAOLE NALU, #304

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $328 to $493/night

    KAMAOLE NALU, #405

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $231 to $292/night

    KIHEI BEACH, #103

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $201 to $280/night

    KIHEI BEACH, #305*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $211 to $292/night

    KIHEI BEACH, #506^

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $347 to $465/night

    ROYAL MAUIAN, #317

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $439 to $504/night

    MENEHUNE SHORES, #218^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $230 to $302/night

    MENEHUNE SHORES, #427^

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $223 to $493/night

    Kihei Surfside, #214^

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $684 to $934/night

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $312 to $455/night

    ROYAL MAUIAN, #403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $550 to $651/night

    ROYAL MAUIAN, #302

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $1,638 to $2,468/night

    INDO LOTUS BEACH HOUSE

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $686 to $934/night

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $246 to $378/night

    KIHEI BEACH, #309

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $201 to $348/night

    SUGAR BEACH RESORT, #418

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $201 to $348/night

    SUGAR BEACH RESORT, #PH23

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $312 to $466/night

    ROYAL MAUIAN, #416

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $253 to $363/night

    KAMAOLE NALU, #603**

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $190 to $236/night

    KEALIA RESORT, #609**

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $403 to $505/night

    ROYAL MAUIAN, #614

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $356 to $869/night

    Maui Eldorado Condo F204

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $428 to $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $512 to $957/night

    Ono Oasis

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $2,505 to $4,766/night

    Mauna Kea Resort Townhouse- Kaunaoa 7B (4BR/4.5BA)

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $518 to $957/night

    Mauna Lani Kamilo #407

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $102 to $278/night

    Tower 1 Suite 707- KP

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $167 to $420/night

    Ilikai Marina 682

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $133 to $154/night

    Discovery Bay 2003

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $174 to $232/night

    Discovery Bay 1201

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $146 to $174/night

    Discovery Bay 2502

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $114 to $167/night

    Discovery Bay 3505

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $94 to $137/night

    Discovery Bay 2608

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $133 to $154/night

    Discovery Bay 1503

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $146 to $174/night

    Discovery Bay 3719

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $240 to $1,678/night

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $238 to $478/night

    Kamako Iki

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $258 to $340/night

    Hale Kamaole 326

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $188 to $258/night

    Hale Kamaole 144

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $258 to $340/night

    Hale Kamaole 221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $317 to $363/night

    Hale Kamaole 249

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $188 to $258/night

    Hale Kamaole 217

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $258 to $340/night

    Hale Kamaole 266

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $258 to $340/night

    Hale Kamaole 264

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $147 to $188/night

    Maui Banyan T103A

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $181 to $300/night

    Hale Mala Hina-245

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $63 to $300/night

    Hale Pineapple

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $134 to $394/night

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $146 to $443/night

    Honua Kai 437

    Studio 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. $134 to $567/night

    Kapalua Villa 21

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $239/night

    Casa De Emdeko 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $467/night

    Kona Plaza#220

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $350/night

    Keauhou Kona Surf & Racquet Club #3-101 "Hale M...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $409/night

    Keauhou Kona Surf & Racquet Club #3-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $525/night

    Kona Pacific A102

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $267/night

    Kona Shores #219

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $239 to $504/night

    Sealodge D8

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $183 to $189/night

    Ferns & Frogs Forest Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $441 to $819/night

    KAPIOLANI- AS SEEN ON HGTV

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $295 to $314/night

    The Green Pineapple Estate

    4 Bedrooms3.5 BathroomsSleeps 10
    30 nights minstay
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $819 to $1,134/night

    Kekua

    4 BedroomsBathroomsSleeps 9
    3 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $68/night

    Hale Iolani Ohana

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