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. $195 to $348/night

    HOL #216

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $164 to $336/night

    HOL 315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $7,860 to $12,620/night

    Kailua Shores Estate 8 Bedroom

    8 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $423 to $810/night

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $595 to $1,280/night

    Hale Kanani (Kaua'i) TVNC 1342

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
  10. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  11. $346 to $822/night

    Hale Oliveira

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
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  13. $815 to $1,858/night

    Hale Pulelehua TVNC#1238

    4 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
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  15. $393 to $643/night

    Nohea Villa

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $1,434 to $3,267/night

    Blue Oasis

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $439 to $504/night

    MENEHUNE SHORES, #515

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $152 to $197/night

    Ke Nani Kai 237

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $169 to $225/night

    Ke Nani Kai 218

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $228 to $458/night

    Hale Ono Loa 101

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  27. $141 to $169/night

    Hotel Molokai 201

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $206 to $336/night

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $152 to $186/night

    Ke Nani Kai 239

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $141 to $169/night

    Paniolo Hale R2

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $624 to $945/night

    Queens Bath Lookout

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $225 to $281/night

    A Ala Hale

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $129 to $169/night

    Wavecrest A203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $456 to $572/night

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $150 to $466/night

    Lai Nani Oceanfront Estate Bungalow #1

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $113 to $152/night

    Wavecrest B209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $225 to $338/night

    Hale Hiamoe

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $121 to $374/night

    Ilikai 804

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $113 to $135/night

    Kepuhi Beach 1234

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $135 to $158/night

    Kepuhi Beach Resort 2222

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $113 to $135/night

    Kepuhi Beach 1192

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $113 to $135/night

    Kepuhi Beach 1182

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $113 to $135/night

    Kepuhi Beach 1226

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $169 to $197/night

    Molokai_Shores 223

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $278 to $341/night

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $516 to $620/night

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $261 to $686/night

    Maui Eldorado Condo F201

    1 BedroomBathroomsSleeps 5
    1 night minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $256 to $661/night

    Maui Eldorado Condo A104

    1 Bedroom BathroomSleeps 5
    1 night minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $256 to $661/night

    Maui Eldorado Condo A202

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $206 to $499/night

    Maui Eldorado Condo K207

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $206 to $499/night

    Maui Eldorado Condo K218

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $141 to $208/night

    Nani Kai Hale # 601

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $197 to $264/night

    Nani Kai Hale # 302

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $152 to $219/night

    Nani Kai Hale # 304

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,688 to $2,250/night

    Hale Lahaina

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $225 to $281/night

    Koa Resort #4F

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $214 to $332/night

    Bay Villa 33B2

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $276 to $366/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $186 to $214/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $276 to $332/night

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $253 to $309/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $428 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $208 to $309/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $276 to $332/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $501 to $619/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $428 to $484/night

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $371 to $484/night

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $236 to $332/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $208 to $253/night

    Molokai Shores 234

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $193 to $359/night

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $231 to $359/night

    Royal Kahana 119 Studio

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $330 to $513/night

    Aina Nalu D202

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $218/night

    Colony Surf 1402

    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. $174 to $202/night

    Colony Surf 1409

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $252 to $292/night

    Sans Souci 807

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $326 to $378/night

    Sea Breeze 9

    2 BedroomsBathroomsSleeps 4
    25 nights minstay
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $174 to $202/night

    Colony Surf 401

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $174 to $239/night

    Colony Surf 609

    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. $113 to $227/night

    Sans Souci 804

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $110 to $136/night

    Colony Surf 803

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $174 to $202/night

    Colony Surf 1807

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $192 to $222/night

    Sans Souci 805

    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. $205 to $237/night

    Sans Souci 1204

    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. $205 to $237/night

    Sans Souci 1105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $174 to $202/night

    Colony Surf 1705

    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. $239 to $277/night

    Colony Surf 504

    2 BedroomsBathroomsSleeps 2
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $144 to $166/night

    Sans Souci 806

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $205 to $237/night

    Sans Souci 204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $348 to $403/night

    Sans Souci PH2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $1,763 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $347 to $786/night

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $246 to $464/night

    Waikoloa Beach Villas B22

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $618 to $1,236/night

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $234 to $431/night

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $283 to $488/night

    Vista Waikoloa B-302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $216 to $464/night

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $234 to $476/night

    Waikoloa Beach Villas H32

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $209 to $464/night

    Vista Waikoloa G-104

    2 Bedrooms2.5 BathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $197 to $407/night

    Waikoloa Beach Villas P32

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $234 to $431/night

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $481 to $896/night

    Ainamalu 29 at Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $234 to $464/night

    Waikoloa Beach Villas N2

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $146 to $163/night

    Koa Resort #2C

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $276 to $297/night

    Hale Kamaole 236

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $258 to $340/night

    Hale Kamaole 222

    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. $125 to $238/night

    Birdsong

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $227 to $441/night

    Island Surf 614

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $175 to $449/night

    Maui Eldorado Condo G101

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $235 to $397/night

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $158 to $239/night

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $144 to $241/night

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $223 to $370/night

    Honua Kai 322

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