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. $18,975 to $28,750/night

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    6 nights minstay
    Pool Hot Tub
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  3. $3,087 to $5,040/night

    Hanalei Beachfront

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
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  5. $1,890 to $3,150/night

    Hale I'a U'i- Beautiful Fish House

    4 Bedrooms5.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
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  7. $1,870 to $2,494/night

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
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  9. $1,688 to $2,250/night

    Hale Lahaina

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
    FREE CANCELLATION
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  11. $1,632/night

    Makana Akua Haena

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  13. $1,624 to $3,884/night

    Haena Beach House TVNC#1258

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
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  15. $1,512 to $2,161/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
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  17. $1,510 to $4,047/night

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $1,347 to $1,732/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
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  21. $1,188 to $3,326/night

    Kona Blue

    5 Bedrooms3.5 BathroomsSleeps 13
    2 nights minstay
    Pool
    FREE CANCELLATION
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  23. $1,157/night

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  25. $1,131 to $3,162/night

    4BD Estate Home (74) at Puako Bay

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
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  27. $1,094 to $1,297/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $1,088 to $1,906/night

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $1,067 to $3,211/night

    3BD Villas at Mauna Kea Resort (39)

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $1,051/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    1 night minstay
    FREE CANCELLATION
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  35. $986 to $2,366/night

    Turtle Bay Villas 301

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
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  37. $986 to $2,366/night

    Turtle Bay Villas 201

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $986 to $2,366/night

    Turtle Bay Villas 304

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
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  41. $986 to $2,366/night

    Turtle Bay Villas 101

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $928 to $2,790/night

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  45. $927 to $1,745/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  47. $907 to $2,455/night

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    2 Bedrooms3.5 BathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $878/night

    Idyllic Oceanfront Cottage with Private Backyard

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $870 to $2,119/night

    Turtle Bay Villas 310

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $870 to $2,119/night

    Turtle Bay Villas 212

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $870 to $2,119/night

    Turtle Bay Villas 112

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $870 to $2,119/night

    Turtle Bay Villas 312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $870 to $2,119/night

    Turtle Bay Villas 307

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $870 to $2,119/night

    Turtle Bay Villas 111

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $870 to $2,119/night

    Turtle Bay Villas 308

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $870 to $2,119/night

    Turtle Bay Villas 315

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $870 to $2,119/night

    Turtle Bay Villas 108

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $870 to $2,119/night

    Turtle Bay Villas 313

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $870 to $2,119/night

    Turtle Bay Villas 113

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $870 to $2,119/night

    Turtle Bay Villas 206

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $869 to $1,531/night

    Turtle Bay Villas 114

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $856 to $1,041/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $840 to $1,260/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $833 to $1,237/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $819 to $1,197/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    4 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $745 to $1,088/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $717 to $904/night

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $687 to $706/night

    Beachfront Condo with Panoramic Ocean Views

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $646 to $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $632 to $1,102/night

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $623 to $748/night

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $579 to $1,139/night

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $577 to $856/night

    Hale Ikena Ko Olina Beach Villa (O1406)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $513 to $962/night

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $513/night

    Hale Kai 2 Ko Olina Beach Villa (B906)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $458 to $740/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $456 to $574/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $456 to $604/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $446 to $619/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $437 to $778/night

    Hale Lanikai Ko Olina Beach Villa (O1104)

    2 BedroomsBathroomsSleeps 4
    6 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $436 to $933/night

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $434 to $775/night

    Hale Lokahi KoOlina Beach Villa (O701)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $429 to $1,066/night

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $428 to $520/night

    Hanalei Colony Resort I1

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $428 to $520/night

    Hanalei Colony Resort F3

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $425 to $899/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $423 to $577/night

    Maui Eldorado I204/205 2Bd/ 2Ba

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $409/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $406 to $1,121/night

    Turtle Bay Villas 305

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $406 to $1,121/night

    Turtle Bay Villas 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $405 to $499/night

    Wilikeiki

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $405 to $563/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $405 to $563/night

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $402 to $458/night

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $401 to $557/night

    Sands Of Kahana 375

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $401 to $557/night

    Sands Of Kahana 237

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $390 to $428/night

    Hanalei Colony Resort M2

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $386 to $459/night

    Moloa'a Bay Cottage

    2 Bedrooms BathroomSleeps 5
    3 nights minstay
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $384 to $667/night

    Napili Point C-12 2bdrm/2bath

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $378 to $775/night

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $374 to $1,204/night

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $374 to $499/night

    Hanalei Colony Resort G1

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $372 to $467/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $372 to $834/night

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $355 to $879/night

    Posh Beachfront Gingerbread Home with 3 Lanais

    3 Bedrooms2.5 BathroomsSleeps 8
    10 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $350 to $374/night

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $349 to $350/night

    Keauhou Kona Surf and Racquet Club 2-204

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $346 to $590/night

    Honua Kai Hokulani 316 1BR

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $342 to $484/night

    Kahana Sunset A4

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $342 to $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $342 to $484/night

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $342 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $342 to $484/night

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $342 to $484/night

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $340 to $494/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $334 to $636/night

    Menehune Shores 405

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $320 to $508/night

    Maui Kai 1005

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $315 to $506/night

    Sands Of Kahana 353

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $315 to $504/night

    Kona Sunshine

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $315 to $506/night

    Sands Of Kahana 334

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $311 to $415/night

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $311 to $444/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $311 to $444/night

    Sands Of Kahana 336

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