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. $295 to $314/night

    The Green Pineapple Estate

    4 Bedrooms3.5 BathroomsSleeps 10
    30 nights minstay
    FREE CANCELLATION
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  3. $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    14 nights minstay
    Pool
  4. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  5. $149 to $168/night

    Vacation Home in Ko Olina Resort

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $295 to $361/night

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $295 to $361/night

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $394 to $471/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $273 to $361/night

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $361 to $438/night

    1 Bedroom Oceanfront #404

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $394 to $471/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $144 to $155/night

    Sans Souci 102

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $205 to $221/night

    Sans Souci 1004

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
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  23. $218 to $281/night

    Colony Surf 104

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
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  25. $239 to $257/night

    Colony Surf 601

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $197 to $210/night

    Colony Surf 1202

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $144 to $155/night

    Sans Souci 203

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $252 to $271/night

    Sans Souci 403/404

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $170 to $210/night

    Colony Surf 809

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $356 to $869/night

    Maui Eldorado Condo F204

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pool
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $194 to $499/night

    Maui Eldorado Condo J120

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $194 to $499/night

    Maui Eldorado Condo K217

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $249 to $624/night

    Maui Eldorado Condo G105

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $169 to $449/night

    Maui Eldorado Condo C101

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $249 to $624/night

    Maui Eldorado Condo B105

    1 Bedroom BathroomSleeps 5
    1 night minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $282 to $415/night

    Regency at Poipu Kai #914

    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. $887 to $3,350/night

    Honua kai Konea 642/643 4 bedroom/4 bath

    4 BedroomsBathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $427 to $1,997/night

    Maui Westside Properties- Hokulani 306

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $291 to $1,488/night

    Maui Westside- Maui Eldorado B206

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $507 to $2,387/night

    Maui Westside Properties Amazing Sunset View K705

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $367 to $1,265/night

    Maui Westside Properties Honua Kai- H712 XL

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $436 to $2,209/night

    Maui Westside Properties- Honua Kai-H836

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $309 to $1,347/night

    Maui Westside:-Honua Kai- Hokulani 930

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $335 to $1,480/night

    Maui Westside Properties Honua Kai- Konea 606

    2 Bedrooms BathroomSleeps 6
    1 night minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $427 to $1,997/night

    Maui Westside Properties: Honua Kai- Hokulani 612

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $565 to $2,666/night

    Maui Westside Properties- Honua Kai- Hokulani 509

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $386 to $869/night

    Maui Eldorado Condo J100

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $141 to $197/night

    Nani Kai Hale # 301

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $152 to $219/night

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $152 to $219/night

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $203 to $287/night

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $124 to $152/night

    Kihei Bay Vista #b203

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  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. $326 to $383/night

    Kahana Sunset A3

    2 Bedrooms2.5 BathroomsSleeps 4
    1 night minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $253 to $366/night

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $276 to $332/night

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $388 to $444/night

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $388 to $422/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $501 to $557/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $276 to $332/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $428 to $484/night

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $225 to $296/night

    Emmalani Suite

    1 Bedroom BathroomSleeps 3
    3 nights minstay
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $304 to $327/night

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $229 to $459/night

    Kamako Iki

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $473 to $547/night

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $188 to $258/night

    Hale Kamaole 131

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $188 to $258/night

    Hale Kamaole 127

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $258 to $340/night

    Hale Kamaole 308

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $188 to $258/night

    Hale Kamaole 155

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $188 to $258/night

    Hale Kamaole 107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $188 to $258/night

    Hale Kamaole 213

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $188 to $258/night

    Hale Kamaole 130

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $258 to $340/night

    Hale Kamaole 221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $235 to $317/night

    Hale Kamaole 311

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $188 to $258/night

    Hale Kamaole 156

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $258 to $340/night

    Hale Kamaole 273

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $188 to $258/night

    Hale Kamaole 207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $276 to $297/night

    Hale Kamaole 171

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $188 to $258/night

    Hale Kamaole 209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $188 to $258/night

    Hale Kamaole 218

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $258 to $340/night

    Hale Kamaole 264

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $258 to $340/night

    Hale Kamaole 266

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $235 to $317/night

    Hale Kamaole 338

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $115 to $188/night

    Maui Banyan T103A

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $340 to $363/night

    Hale Kamaole 249

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $188 to $258/night

    Hale Kamaole 164

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $388 to $444/night

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $251 to $596/night

    Honua Kai 506

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $223 to $567/night

    Kapalua Villa 21

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $151 to $202/night

    Island Surf 402

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $304 to $428/night

    Hanalei Colony Resort M2

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $304 to $586/night

    Hanalei Colony Resort F3

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $239 to $413/night

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $409/night

    Keauhou Kona Surf & Racket Club Townhouse #4

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $239 to $504/night

    Sealodge D8

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $158 to $189/night

    Ferns & Frogs Forest Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $819 to $1,134/night

    Kekua

    4 BedroomsBathroomsSleeps 9
    3 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $1,512 to $1,890/night

    Oceanfront Blackpoint

    3 Bedrooms3.5 BathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $68/night

    Hale Iolani Ohana

    1 Bedroom BathroomSleeps 2
    31 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $1,890/night

    Weke Road Beachfront Cottage

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $139 to $158/night

    Hale Ola Aina

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $295 to $314/night

    Haleiwa Surf Condo

    1 BedroomBathroomsSleeps 4
    14 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $1,890 to $2,363/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $1,512 to $2,161/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $120 to $139/night

    Big Island Sanctuary

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $819 to $1,575/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $1,008 to $1,260/night

    Exquisite Balinese Beachfront

    4 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $1,071 to $1,351/night

    Modern Mokuleia Beachfront

    4 BedroomsBathroomsSleeps 6
    7 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $756 to $1,890/night

    Hanalei Bay View

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $158/night

    Big Island Bali Hideaway

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $2,141 to $3,780/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $321 to $441/night

    Turtle Bay Resort Condo

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations