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. $378 to $508/night

    Turtle Bay Bird of Paradise

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $346 to $497/night

    Turtle Bay NorthShore Haven

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $270 to $346/night

    Turtle Bay 19th Hole

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  7. $410 to $486/night

    Turtle Bay Paniolo

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  9. $270 to $447/night

    Turtle Bay Papaya Hale

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $90 to $398/night

    Kaanapali Shores 742 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $203 to $813/night

    Kahana Sunset C7 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  15. $148 to $952/night

    Whaler 518 OceanView Studio Condo

    Studio BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $310 to $624/night

    Bay Villa 24G3

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $177 to $624/night

    Kahana Sunset A3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $379 to $781/night

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $227 to $985/night

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $219 to $650/night

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $414 to $1,149/night

    Sands Of Kahana 237

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $392 to $985/night

    Sands Of Kahana 334

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $4,200/night

    Timeshare Week

    3 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $317 to $820/night

    Sands Of Kahana 317

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $4,200/night

    Timeshare Condo

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $353 to $624/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $353 to $624/night

    Kahana Sunset D5

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $156 to $361/night

    Valley Isle Resort 507

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $388 to $703/night

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $331 to $415/night

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $467 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $961 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $320 to $493/night

    Pali Ke Kua #241

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $362 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $331 to $415/night

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $224 to $729/night

    Napili Shores A203 Ocean Front Studio

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $324 to $410/night

    Turtle Bay Deep Blue

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $410 to $486/night

    Turtle Bay Wicked Wahine

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $263 to $576/night

    Maui Kaanapali Villas #B133

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $274 to $395/night

    Beautiful Hawaiian Oceanfront Condo w private lanai and ...

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $373 to $428/night

    Luxurious Penthouse w panoramic ocean views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $385 to $435/night

    Hale Kania Kai at Surf & Racquet 3302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $210 to $420/night

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $288 to $1,149/night

    Sands Of Kahana 375

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $194 to $525/night

    Kona Alii 401

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $305 to $593/night

    The Mahana #1017

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $520 to $625/night

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,695 to $2,712/night

    Hale Hoku

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $388 to $457/night

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $151 to $344/night

    Kuleana 706 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $118 to $398/night

    Kaanapali Shores 422 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $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
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $159 to $478/night

    Royal Kahana 318 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $147 to $337/night

    Royal Kahana 702 Studio Condo

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $351 to $1,116/night

    Papakea H404 3 bedroom condo

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $270 to $951/night

    Whaler 616 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $363 to $1,094/night

    Residences at Napili Bay B7 3 Bedroom

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $272 to $1,082/night

    Kapalua Bay Vill 23G1 Ocean front 1 BD/1BA

    1 Bedroom1.5  BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $272 to $1,082/night

    Kapalua Bay Villa 30G1

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $441 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $339 to $1,139/night

    Kulalani 2003

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $279 to $659/night

    Lae Nani 333, Oceanview, Renovated and Gated

    1 Bedroom1.5  BathroomSleeps 2
    3 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $184 to $525/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $214 to $247/night

    Beautifully Upgraded, Full Kitchen, Comfy King Bed, AC

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $284 to $509/night

    Kahana Reef #122

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $299 to $446/night

    Halii Kai 3D

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $1,202 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $394 to $1,050/night

    Makana Kai Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $936 to $2,531/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    3 nights minstay
    Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $378 to $464/night

    Turtle Bay Alea Condo

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $499 to $735/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $445 to $758/night

    Papakea #G106

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $152 to $335/night

    Valley Isle #1206

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $231 to $440/night

    Valley Isle #1209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $194 to $440/night

    Valley Isle #1203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $209 to $395/night

    Valley Isle #302

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $420 to $813/night

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $126 to $291/night

    Royal Kahana #319

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $315 to $488/night

    Pikake #A6

    2 Bedrooms1.5  BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $260 to $570/night

    Papakea #L407

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $226 to $505/night

    Maui Kaanapali Villas #C152

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $368 to $798/night

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $170 to $417/night

    Maui Kaanapali Villas #B242

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $275 to $592/night

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $308 to $531/night

    Kahana Reef #404

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $143 to $368/night

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $165 to $412/night

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $252 to $364/night

    Maui Kaanapali Villas #C255

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $336 to $887/night

    Kaanapali Royal #N302

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $520 to $851/night

    Papakea #A109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $194 to $499/night

    Maui Kaanapali Villas #B143

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $226 to $429/night

    Kahana Reef #322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $143 to $368/night

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $125 to $420/night

    Kona Mansions#105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $210 to $525/night

    Kona Pacific A102

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $184 to $420/night

    Casa De Emdeko 237

    1 Bedroom1.5  BathroomSleeps 4
    3 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $251 to $525/night

    Magic Sands Retreat Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $184 to $525/night

    White Sands Village#225

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $299 to $525/night

    Keauhou Kona Surf & Racquet Club#3-204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $205 to $768/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $362 to $467/night

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $388 to $572/night

    Puu Poa #305

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $275 to $1,082/night

    Kapalua Bay Villa 29B4

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