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. $6,215 to $7,910/night

    Hanalei Beach Estate

    5 Bedrooms5.5 BathroomsSleeps 13
    3 nights minstay
    Hot Tub
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  3. $3,035 to $11,631/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,958 to $11,468/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $2,260 to $5,629/night

    Hanalei Beachfront Hale

    3 Bedrooms3.5 BathroomsSleeps 8
    3 nights minstay
    Hot Tub
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  9. $1,846 to $6,200/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  13. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  15. $1,349 to $1,609/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
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  17. $1,243 to $3,127/night

    Bond House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
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  19. $1,220 to $4,156/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $1,096 to $5,113/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $1,074 to $2,182/night

    Spindrift Kauai

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $1,049 to $1,752/night

    Makana Akua Haena

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
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  27. $1,038 to $3,879/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $1,017 to $3,146/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $998 to $1,587/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  33. $989 to $2,906/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $935 to $1,767/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $923 to $2,740/night

    Polo Beach Club 106

    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. $923 to $2,546/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 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. $918 to $2,312/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $898 to $2,528/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $866 to $1,560/night

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $849 to $1,816/night

    Kona Luxe Ocean Villa with Pool & Hot Tub

    4 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $808 to $2,974/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $763 to $1,747/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $735 to $1,427/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $721 to $2,362/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $701 to $3,474/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $695 to $1,243/night

    Puu Poa 303

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $687 to $1,176/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $668 to $2,681/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $659 to $2,025/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $656 to $2,986/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $647 to $1,245/night

    Kahana Outrigger #4B2

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $635 to $756/night

    Waipouli Beach Resort G-404

    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. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $625 to $935/night

    The Mahana #1205

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $625 to $788/night

    The Mahana #1217

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $604 to $2,924/night

    Makena Surf F201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $603 to $2,216/night

    Kauai Poipu Kapili 51

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $577 to $1,644/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $576 to $1,374/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $554 to $1,824/night

    Mana Kai #705

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $549 to $1,583/night

    Mana Kai #303

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $549 to $1,916/night

    Big Island Kona Reef D-22

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $541 to $1,833/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $536 to $1,499/night

    Mana Kai #307

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $532 to $840/night

    The Mahana #1204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $528 to $1,513/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $520 to $1,883/night

    Mana Kai #614

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $520 to $851/night

    Papakea #A109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $520 to $1,883/night

    Mana Kai #814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $520 to $1,689/night

    Honua Kai Hokulani 310

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $520 to $2,059/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $491 to $1,583/night

    Royal Mauian 512

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $485 to $1,700/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $480 to $1,726/night

    Poipu Shores 301B

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $474 to $1,306/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $473 to $637/night

    Moloa'a Bay Cottage

    1 Bedroom BathroomSleeps 4
    3 nights minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $467 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $467 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $467 to $1,449/night

    Mana Kai #815

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $458 to $1,608/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $441 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $438 to $1,254/night

    Sands of Kahana 281

    2 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $426 to $1,480/night

    Big Island Kona Bali Kai 301

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $425 to $648/night

    Papakea #A201

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $420 to $813/night

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $414 to $1,149/night

    Sands Of Kahana 237

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $408 to $815/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $404 to $1,571/night

    Mana Kai #508

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $404 to $1,100/night

    Maalaea Surf G8

    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. $404 to $1,612/night

    Kauai Aliomanu

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $404 to $737/night

    Big Island Kona Nalu 203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $404 to $1,221/night

    Maui Sunset B217

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $403 to $1,407/night

    Kamaole Nalu 504

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $394 to $1,050/night

    Makana Kai Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $394 to $735/night

    Hale Mahina #B403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $394 to $741/night

    Papakea #F407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $392 to $985/night

    Sands Of Kahana 334

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $387 to $1,061/night

    Sands Of Kahana 315 2Bd/2Ba Oceanfront

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $379 to $1,030/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $375 to $1,011/night

    Kihei Surfside 506

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $375 to $1,033/night

    Kihei Surfside 412

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $374 to $766/night

    Honua Kai Hokulani 824

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $373 to $428/night

    Luxurious Penthouse w panoramic ocean views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $372 to $485/night

    Kona Palms 304

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $362 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $362 to $1,257/night

    Menehune Shores 112

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $361 to $1,118/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $361 to $1,118/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $359 to $985/night

    Sands Of Kahana 353

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $353 to $1,387/night

    Kamaole Nalu 402

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations