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. $204 to $557/night

    Kamaole Sands 8-206

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $329 to $1,780/night

    Grand Champions 170

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $312 to $1,170/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $414 to $1,347/night

    Palms at Wailea 403

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $808 to $2,974/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $184 to $867/night

    Big Island Waikoloa Shores 308

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $231 to $959/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $306 to $1,324/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $318 to $1,130/night

    Wailea Ekahi 53D

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $190 to $566/night

    Maui Vista 2212

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $260 to $1,029/night

    Big Island Waikoloa Colony Villas 2404

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $284 to $931/night

    Maui Parkshore 204

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $289 to $849/night

    Milowai 101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $234 to $748/night

    Vista Waikoloa B302

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $170 to $254/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $565 to $678/night

    Helen's Beach House

    5 BedroomsBathroomsSleeps 12
    7 nights minstay
    Pool
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $345 to $565/night

    Pali Ke Kua #237

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $316 to $760/night

    Hale Kahana'lu

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $118 to $280/night

    Peace of Paradise

    1 Bedroom1.25  BathroomSleeps 2
    3 nights minstay
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $305 to $715/night

    Hale Ki'i Maka Manu

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $220 to $237/night

    Hale O Makani

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $356 to $565/night

    Villas of Kamalii 43

    3 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $231 to $630/night

    Kahalu'u Bay Villas #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $735 to $1,427/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $127 to $328/night

    Tropical Island Paradise

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $1,243 to $3,127/night

    Bond House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $254 to $582/night

    Lae Nani 434

    1 Bedroom1.5  BathroomSleeps 2
    3 nights minstay
    Pool
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $678 to $754/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $308 to $730/night

    Villas of Kamalii 47

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $218 to $571/night

    Sugar Beach 502

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $76 to $458/night

    Maluhia Kahakai

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $406 to $620/night

    Luana Kai C-301

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $136 to $237/night

    Maui Sunset B204

    1 BedroomBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $254 to $782/night

    Island Surf 614

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $678 to $1,751/night

    Haena Place

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $480 to $1,726/night

    Poipu Shores 301B

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $763 to $1,559/night

    Kamapua'a Hale

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $339 to $622/night

    Nihilani 32C

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $339 to $990/night

    Poipu Palms 102

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $277 to $469/night

    Emmalani Court 312

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,175 to $3,334/night

    Hale Naninoa

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $254 to $617/night

    Makani Ea Home

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $904 to $1,243/night

    Haena Kai

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $156 to $363/night

    Hale O Nani Mala Pua

    3 Bedrooms2.75 BathroomsSleeps 6
    3 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $338 to $943/night

    Grand Melemele

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $277 to $601/night

    Villas of Kamali'i 38

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $333 to $509/night

    Maalaea Kai #410

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $141 to $186/night

    Sandpiper 216B

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $271 to $807/night

    Hololani B802

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,356 to $2,961/night

    Hanalei Zen Retreat

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $229 to $475/night

    Pono Kai H204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $107 to $308/night

    Waiakea Villas 4329

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $942 to $1,054/night

    Sea Turtle Ranch

    4 BedroomsBathroomsSleeps 8
    29 nights minstay
    Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $339 to $803/night

    Halehikiola

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $332 to $889/night

    Waipouli D405

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $455 to $897/night

    Puu Poa 213

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $452/night

    Sky Ala Moana 809

    2 BedroomsBathroomsSleeps 4
    29 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $74 to $269/night

    Cheerful Hawaiian Monarch Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $77 to $294/night

    Radiant Hawaiian Monarch Studio

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $112 to $499/night

    Pacific Monarch Paradise

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $97 to $412/night

    Central Kalakauan Apartment

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $74 to $253/night

    Delightful Hawaiian Monarch Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $104 to $414/night

    Gorgeous One Bedroom Bamboo Blocks from the Beach

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $74 to $286/night

    Bright Waikiki Monarch Studio

    Studio BathroomSleeps 3
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $164 to $313/night

    Lanikea Ocean View Apartment

    2 BedroomsBathroomsSleeps 4
    30 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $77 to $355/night

    Refreshing Inn on The Park

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $97 to $411/night

    Bright Kalakauan Apartment

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $87 to $346/night

    Sophisticated Palms Waikiki Studio

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $373 to $562/night

    Colony Villas at Waikoloa Beach Resort #1305

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $264 to $468/night

    WAILEA EKOLU, #312

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $91 to $179/night

    Chic Waikiki Skytower Apartment

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $189 to $599/night

    OCEAN VIEW 2 BEDROOM DOWNTOWN CONDO- WALK TO RESTAURANTS...

    2 Bedrooms1.5  BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $129 to $399/night

    NAUTICAL THEME GARDEN VIEW STUDIO- KONA ISLANDER INN CON...

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $129 to $399/night

    GARDEN VIEW STUDIO- KONA ISLANDER INN CONDOS

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $407 to $784/night

    Mana Kai Maui Resort #314C

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $56 to $144/night

    Fairway Villa 30 Day Minimum

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $125 to $685/night

    Maui Kai 1005 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $281 to $421/night

    Turtle Bay Hale Lilly

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $313 to $389/night

    Turtle Bay Hale Mokulani

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $313 to $389/night

    Turtle Bay Garden Hale

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $367 to $486/night

    Turtle Bay Sage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $115 to $379/night

    Big Island Kona Kai D3

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $176 to $612/night

    Big Island Keauhou Punahele E202

    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. $183 to $626/night

    Big Island Lunapule Condos 104

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $161 to $478/night

    Big Island Kona Makai 4205

    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. $220 to $888/night

    Big Island Waikoloa Fairways B-214

    2 Bedrooms2.5 BathroomsSleeps 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. $208 to $722/night

    Big Island Keauhou Surf & Racquet 181

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $132 to $320/night

    Oahu Royal Garden at Waikiki 1711

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $283 to $1,102/night

    Big Island Kona Pacific A306

    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. $203 to $848/night

    Big Island Waikoloa Hills 1304

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $230 to $619/night

    Big Island Keauhou Akahi 408

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $346 to $1,325/night

    Big Island Waikoloa Colony Villas 801

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $313 to $389/night

    Turtle Bay Protea

    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. $389 to $486/night

    Turtle Bay Anthurium

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $269 to $475/night

    Turtle Bay Sea Breeze Condo

    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. $270 to $367/night

    Experience Turtle Bay Lilikoi

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $247 to $671/night

    Panoramic Ocean View 1BR Condo Suite 150 feet from the O...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $208 to $648/night

    Puamana 18B

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations