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. $249 to $327/night

    Papakea A108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
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  3. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  5. $208 to $315/night

    Papakea J103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  7. $505 to $564/night

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
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  9. $259 to $447/night

    Papakea #E207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $209 to $539/night

    Kaanapali Royal #E302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  13. $215 to $435/night

    Lahaina Shores #225

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $259 to $505/night

    Lahaina Shores #533

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $1,096 to $3,067/night

    Ali'i Point

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $145 to $534/night

    Pohailani #102

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $307 to $725/night

    Mahana Resort #1107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $419 to $751/night

    Hololani A303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $319 to $1,038/night

    Royal Kahana #1211

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $259 to $493/night

    Mahana Resort #813

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $374 to $1,604/night

    Papakea B405

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $230 to $469/night

    Keawakapu 208

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $255 to $986/night

    Lokelani #A205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  35. $371/night

    Papakea #A201

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
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  37. $215 to $464/night

    Papakea #F105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $516 to $620/night

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $245 to $461/night

    Maui Kai 206

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $162 to $447/night

    Lahaina Roads #204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $203 to $447/night

    Kaanapali Plantation #52

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  47. $238 to $597/night

    Papakea #L207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $215 to $586/night

    Lahaina Shores #317

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $197 to $493/night

    Maui Kaanapali Villas #B247

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $146 to $163/night

    Koa Resort #2C

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $563 to $1,044/night

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $506 to $1,099/night

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $215 to $481/night

    Mahana Resort #1003

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $363 to $864/night

    Kapalua Ridge Villa #311

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $162 to $505/night

    Lahaina Roads #205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $246 to $384/night

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $303 to $737/night

    Kaanapali Plantation #28

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $249 to $545/night

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $278 to $341/night

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $396 to $723/night

    Wailea Ekolu 1606

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $333 to $666/night

    Papakea L108

    1 Bedroom 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. $230 to $454/night

    Maui Sands Seaside 718

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $259 to $496/night

    Maui Kai 108

    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. $288 to $543/night

    Papakea K306

    1 Bedroom 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. $249 to $312/night

    Hanalei Bay Villa #17

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $2,336 to $5,088/night

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $336 to $806/night

    Maui Eldorado Condo D100

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $221 to $405/night

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $253 to $508/night

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $315 to $511/night

    Maui Kai 605

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $381 to $665/night

    Kaanapali Royal E101

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $344 to $549/night

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $221 to $545/night

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $316 to $503/night

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $225 to $281/night

    Koa Resort #4F

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $367 to $948/night

    Maui Westside Properties Honua Kai- H712 XL

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $335 to $917/night

    Maui Westside Properties- Hokulani 108 1 bedroom.

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $578 to $1,908/night

    Maui Westside Properties- Honua Kai H709

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $296 to $1,041/night

    Maui Westside- Maui Eldorado B206

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $136 to $218/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $97 to $120/night

    Peace of Paradise

    1 Bedroom1.25  BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $541 to $901/night

    Haleiwa Sunshine

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $125 to $158/night

    Hale Anuenue Nuku- The Rainbows End

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $174 to $188/night

    Colony Surf 1409

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $152 to $164/night

    Colony Surf 403

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $218/night

    Colony Surf 1402

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $134/night

    Paradise Cliff House

    2 BedroomsBathroomsSleeps 4
    31 nights minstay
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $326 to $350/night

    Sea Breeze 9

    2 BedroomsBathroomsSleeps 4
    27 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $197 to $210/night

    Sans Souci 1104

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $1,474 to $2,520/night

    Luxury at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $1,701 to $2,520/night

    Helen's Beach House

    6 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $252 to $271/night

    Sans Souci 807

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $174 to $188/night

    Colony Surf 401

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $174 to $239/night

    Colony Surf 609

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $737 to $1,197/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    4 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $113 to $210/night

    Sans Souci 804

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $110 to $126/night

    Colony Surf 803

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $108 to $139/night

    Hilo Hale Kaumana

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $57 to $68/night

    Volcano Dancing Bamboo Cottage

    1 Bedroom BathroomSleeps 2
    31 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $227 to $270/night

    The Green Pineapple Main House

    3 BedroomsBathroomsSleeps 8
    30 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $174 to $188/night

    Colony Surf 1807

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $192 to $205/night

    Sans Souci 805

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $205 to $221/night

    Sans Souci 1204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $1,260 to $1,531/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $199 to $246/night

    Black Sand Beach House

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $1,512 to $2,520/night

    Leimoku

    5 Bedrooms4.5 BathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $244 to $410/night

    Hale Kahana'lu

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $205 to $221/night

    Sans Souci 1105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $205 to $221/night

    Sans Souci 201

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $669/night

    Pualele

    5 Bedrooms5.5 BathroomsSleeps 10
    31 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $174 to $188/night

    Colony Surf 1705

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $1,260 to $1,531/night

    Mokuleia Beach House

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $239 to $257/night

    Colony Surf 504

    2 BedroomsBathroomsSleeps 2
    3 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $144 to $155/night

    Sans Souci 806

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $625/night

    The Ka Lani Mai House

    4 Bedrooms4.5 BathroomsSleeps 8
    31 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $539 to $627/night

    Pu'u Po'a #108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $205 to $221/night

    Sans Souci 204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $348 to $374/night

    Sans Souci PH2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $210 to $233/night

    Volcano Dancing Ferns Main House

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $97 to $120/night

    Pauole Hale

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $142 to $189/night

    Papai Lanai

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $204 to $415/night

    Waikoloa Beach Villas O-33

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $109 to $147/night

    Wavecrest B209

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