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. $125 to $685/night

    Maui Kai 1005 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  3. $310 to $940/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  4. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  5. $359 to $985/night

    Sands Of Kahana 353

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $329 to $1,306/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $228 to $985/night

    Sands of Kahana 255

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  10. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  11. $474 to $1,306/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  12. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  13. $310 to $1,306/night

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  14. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  15. $438 to $1,254/night

    Sands of Kahana 281

    2 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $362 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $203 to $271/night

    Maui Sunset B110

    1 BedroomBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $886 to $1,611/night

    MAKENA SURF, #F-209

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $250 to $688/night

    Honua Kai Hokulani 316 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $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
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $310 to $1,306/night

    Sands Of Kahana 215

    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. $438 to $652/night

    WAILEA ELUA, #2101*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $917 to $1,835/night

    WAILEA ELUA, #1404

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $244 to $784/night

    SUGAR BEACH RESORT, #319

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $387 to $1,061/night

    Sands Of Kahana 315 2Bd/2Ba Oceanfront

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $177 to $420/night

    Keauhou Kona Surf & Racquet Club #7

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $188 to $525/night

    Kona Makai 6-305

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $142 to $293/night

    Kona Makai 5-303

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pool Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $244 to $784/night

    Sugar Beach Resort, #130*

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $580 to $1,172/night

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $560 to $1,529/night

    WAILEA ELUA, #2202

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $407 to $866/night

    WAILEA ELUA, #0106

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $254 to $784/night

    SUGAR BEACH RESORT, #414

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $2,131 to $2,855/night

    MAKENA SURF, #G-301-302

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $294 to $888/night

    Papakea K406 OceanView 2 Bedroom 2 bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $164 to $582/night

    36th Floor Deluxe Ocean View Condo with Free Parking &am...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $90 to $398/night

    Kaanapali Shores 742 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $148 to $952/night

    Whaler 518 OceanView Studio Condo

    Studio BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $227 to $985/night

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $414 to $1,149/night

    Sands Of Kahana 237

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $392 to $985/night

    Sands Of Kahana 334

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $317 to $820/night

    Sands Of Kahana 317

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $467 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $224 to $729/night

    Napili Shores A203 Ocean Front Studio

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $288 to $1,149/night

    Sands Of Kahana 375

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $652 to $1,172/night

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $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
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $351 to $1,116/night

    Papakea H404 3 bedroom condo

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $270 to $951/night

    Whaler 616 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $441 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $184 to $525/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,020 to $1,458/night

    MAKENA SURF, #G-304

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $764 to $1,529/night

    WAILEA ELUA, #1104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $886 to $1,611/night

    MAKENA SURF, #F-212

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $254 to $784/night

    SUGAR BEACH RESORT, #418

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $205 to $768/night

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $198 to $630/night

    Sea Village 4-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $335 to $525/night

    Kona Makai 2-201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $250 to $344/night

    Kona Reef D-32

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $764 to $1,611/night

    MAKENA SURF, #F-110

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $509 to $866/night

    WAILEA ELUA, #2106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $175 to $985/night

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $849 to $1,816/night

    Kona Luxe Ocean Villa with Pool & Hot Tub

    4 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $154 to $576/night

    Cliffs 5205

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $605 to $1,243/night

    Cliffs 8301

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $314 to $525/night

    Kona Makai 1-301

    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. $149 to $399/night

    OUTSTANDING OCEANFRONT STUDIO- KONA ISLANDER INN CONDOS

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $254 to $776/night

    Big Island Keauhou Surf & Racquet 1204

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $155 to $558/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $467 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $110 to $398/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $968 to $1,835/night

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $132 to $388/night

    Napili Shores D229 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $408 to $815/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $241 to $729/night

    Napili Shores A106 Studio Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $217 to $685/night

    Papakea C207 Studio Condo

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $298 to $892/night

    Mahana 209 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $263 to $794/night

    Mahana 604 Oceanfront 1BD/1BA

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $229 to $691/night

    Maui Kai 805 Ocean View 1 bedroom/1 bath

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $217 to $685/night

    Papakea H107 AC, King Bed, Ground Corner Unit

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $379 to $1,030/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $202 to $610/night

    Napili Shores G154 Ocean View Studio

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $163 to $624/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $223 to $672/night

    Maui Kai 908 Oceanfront 1 Bedroom

    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. $346 to $1,020/night

    Hale Mahina #B-405

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $489 to $1,121/night

    SUGAR BEACH RESORT, #535^

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $142 to $293/night

    Kona Makai 3-302

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $244 to $685/night

    SUGAR BEACH RESORT #121

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $249 to $944/night

    Kona Coast, Fantastic Ocean View & Pool

    3 Bedrooms BathroomSleeps 6
    1 night minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $218 to $571/night

    Sugar Beach 502

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $136 to $237/night

    Maui Sunset B204

    1 BedroomBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $541 to $1,833/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations