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. $368/night

    Papakea #F108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $1,120 to $3,370/night

    Wailea Beach Villas M312

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $339 to $804/night

    Halehikiola

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
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  7. $829 to $856/night

    Park Lane 3300

    3 Bedrooms2.5 BathroomsSleeps 6
    30 nights minstay
    Pool Hot Tub
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  9. $109 to $136/night

    Alii Villas 218

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
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  11. $942 to $1,055/night

    Sea Turtle Ranch

    4 BedroomsBathroomsSleeps 8
    30 nights minstay
    Hot Tub
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  13. $628 to $989/night

    Liho Kai

    4 Bedrooms3.5 BathroomsSleeps 9
    4 nights minstay
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  15. $115 to $195/night

    Trendy Central Honolulu Apartment

    2 Bedrooms BathroomSleeps 4
    30 nights minstay
    FREE CANCELLATION
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  17. $389 to $789/night

    Kapalua Golf Villas 15P5-6

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  19. $301 to $312/night

    2987 Kalakaua #705

    2 BedroomsBathroomsSleeps 4
    30 nights minstay
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  21. $202 to $436/night

    Kihei Resort 119

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $213 to $511/night

    Big Island Waikoloa Fairways B-214

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $280 to $605/night

    Pacific Shores B113

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $364 to $905/night

    Grand Champions 40

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $364 to $905/night

    Grand Champions 30

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $113 to $323/night

    Cozy Sunset Views w/ Lanai- Close to Beach

    1 Bedroom BathroomSleeps 2
    1 night minstay
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $113 to $323/night

    Charming Pu'ukala Sunset- Near Hiking and Golf

    1 Bedroom BathroomSleeps 2
    1 night minstay
    FREE CANCELLATION
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  35. $245 to $988/night

    Pu'ukala Sunset Estate w/ Amazing Ocean Views!

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    FREE CANCELLATION
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  37. $223 to $801/night

    Kihei Surfside 506

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  39. $252 to $818/night

    Kihei Surfside 412

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $157 to $498/night

    Big Island Casa De Emdeko A308

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
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  43. $286 to $600/night

    Big Island Waikoloa Colony Villas 1206

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $246 to $559/night

    Kauai Kailani 219

    2 Bedrooms BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $264 to $468/night

    KIHEI BEACH, #507

    1 BedroomBathroomsSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $364 to $1,081/night

    Kapalua Golf Villas 27P7

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
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  51. $1,064 to $3,199/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $156 to $395/night

    Big Island Kona Makai 4205

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $224 to $543/night

    Kamaole Beach Royale 307

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $291 to $688/night

    Sugar Beach Resort 328

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $248 to $330/night

    Kealakekua Vista

    3 BedroomsBathroomsSleeps 8
    30 nights minstay
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $207 to $681/night

    Big Island Lunapule Condos 104

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $364 to $994/night

    Big Island Holua Kai 7072

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $172 to $604/night

    Napili Shores F147

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $374 to $616/night

    Kahana Sunset D5

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $374 to $616/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $355 to $543/night

    Kahana Sunset D11

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $638 to $1,014/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $725 to $1,435/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $170 to $681/night

    Big Island Keauhou Punahele E202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $126 to $420/night

    Kona Mansions#105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $151 to $545/night

    Big Island Keauhou Punahele A103

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $315 to $692/night

    Paki Maui #103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $210 to $456/night

    Maui Sands #6E

    2 Bedrooms BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $143 to $420/night

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $756 to $2,192/night

    Kahana Outrigger 2B2

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $243 to $644/night

    New! Waikoloa Beach Villas F22

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $198 to $525/night

    Kona Alii 401

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $308 to $590/night

    Kauai Manualoha 703

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $168 to $379/night

    Oahu Tradewinds Plaza

    Studio BathroomSleeps 2
    4 nights minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $115 to $307/night

    Big Island Kona Kai D3

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $116 to $183/night

    Harbor View Plaza Apartment

    2 Bedrooms1.5  BathroomSleeps 4
    28 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $160 to $681/night

    Big Island Kona Plaza 311

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $331 to $1,153/night

    Kahana Village 13 Oceanview 3Bed/2Bath

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $280 to $801/night

    Napili Point B35

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $107 to $316/night

    Waiakea Villas 4329

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $141 to $203/night

    Alii Cove#S1

    3 BedroomsBathroomsSleeps 8
    31 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $336 to $984/night

    Palms at Wailea 2104

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $448 to $1,313/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $252 to $650/night

    Maalaea Banyans 217

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $346 to $936/night

    Wailea Ekahi 40D

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $173 to $357/night

    Keauhou Kona Surf & Racquet Club #6-201

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $896 to $2,044/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $3,192 to $9,254/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $569 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $255 to $862/night

    Picturesque Pacific Monarch

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $177 to $420/night

    Waikoloa Fairways #A310

    2 Bedrooms2.5 BathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $97 to $417/night

    Bright Kalakauan Apartment

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $364 to $821/night

    Milowai 101

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $188 to $473/night

    Keauhou Kona Surf & Racquet Club Townhouse#183

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $305 to $560/night

    ROYAL MAUIAN #219

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $532 to $1,312/night

    Wailea Ekahi 39E

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $280 to $625/night

    Maui Vista 3411

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $173 to $630/night

    Holualoa Bay Villas#103

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $156 to $525/night

    Kona Mansions#211

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $71 to $279/night

    Happy Hawaiian Monarch Studio

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $152 to $315/night

    Kona Makai 2-303

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $103 to $366/night

    Breezy Luana Waikiki

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $252 to $782/night

    Mahina Surf 111

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $406 to $581/night

    Pats at Punaluu 615

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $178 to $365/night

    Tower 1 Suite 3514- KP

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $167 to $435/night

    Pats at Punaluu 303

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $280 to $612/night

    Kihei Ali'i Kai B108

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $1,017 to $1,993/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    4 nights minstay
    Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $924 to $1,908/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $895 to $2,006/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $820 to $1,963/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $295 to $468/night

    KIHEI BEACH #504

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $305 to $478/night

    Menehune Shores #423

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $305 to $540/night

    Maalaea Surf #G-2

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $325 to $478/night

    MENEHUNE SHORES #209

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $540 to $764/night

    MENEHUNE SHORES #210

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $223 to $591/night

    Kihei Surfside, #511

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $309 to $648/night

    Big Island Kailua Bay Resort 2302

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $478 to $1,226/night

    Big Island Holua Kai 111

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $244 to $522/night

    Kihei Ali'i Kai D201

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $565 to $584/night

    Star of Hawaii

    4 BedroomsBathroomsSleeps 12
    30 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $487 to $1,499/night

    Big Island Holua Kai 7066

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $379 to $952/night

    Big Island Kolea 14H

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $254 to $501/night

    Pono Kai H204

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $426 to $1,136/night

    Royal Mauian 216

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