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. $931 to $3,555/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  2. $476 to $1,616/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  3. $324 to $931/night

    The Cottage

    The Cottage

    1 Bedroom BathroomSleeps 4
    2 nights minstay
  4. $150 to $768/night

    AlohaDays Kalakauan #410

    AlohaDays Kalakauan #410

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    FREE CANCELLATION
  5. $978 to $1,166/night

    Punahele Point

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
  6. $174 to $731/night

    Waikiki Banyan 2206-2 *Legal Vacation Rental

    Waikiki Banyan 2206-2 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  7. $500 to $1,402/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  8. $333 to $393/night

    Song of the Ocean

    Song of the Ocean

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
  9. $549 to $926/night

    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  10. $146 to $183/night

    Perfect for Extended Stays! Two Pools & Two Hot Tubs

    Perfect for Extended Stays! Two Pools & Two Hot Tubs...

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $160 to $385/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $111 to $346/night

    Papakea D108

    Papakea D108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $146 to $281/night

    Island Surf 306

    Island Surf 306

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $124 to $353/night

    Kona Magic Sands #111

    Kona Magic Sands #111

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $125 to $336/night

    Marine Surf Waikiki 2206

    Marine Surf Waikiki 2206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $113 to $374/night

    Marine Surf Waikiki 2108

    Marine Surf Waikiki 2108

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $138 to $324/night

    Marine Surf Waikiki 1605

    Marine Surf Waikiki 1605

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $113 to $286/night

    Marine Surf Waikiki 2106

    Marine Surf Waikiki 2106

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $113 to $324/night

    Marine Surf Waikiki 908

    Marine Surf Waikiki 908

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $580 to $783/night

    Wailea Ekahi #34-C

    Wailea Ekahi #34-C

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $1,137 to $2,743/night

    Ke Kailani Hale A2

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  22. $178 to $427/night

    KIHEI SURFSIDE, #608

    KIHEI SURFSIDE, #608

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
  23. $110 to $321/night

    Ilikai Marina 1783

    Ilikai Marina 1783

    1 Bedroom BathroomSleeps 3
    1 night minstay
    FREE CANCELLATION
  24. $128 to $353/night

    Ilikai Tower 611

    Ilikai Tower 611

    1 Bedroom BathroomSleeps 3
    1 night minstay
    Pool
    FREE CANCELLATION
  25. $184 to $542/night

    Ilikai Tower 2024

    Ilikai Tower 2024

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  26. $0/night

    Discovery Bay 1002

    Discovery Bay 1002

    1 Bedroom BathroomSleeps 2
    FREE CANCELLATION
  27. $94 to $174/night

    Discovery Bay 3308

    Discovery Bay 3308

    1 Bedroom BathroomSleeps 4
    1 night minstay
    FREE CANCELLATION
  28. $110 to $203/night

    Discovery Bay 2612

    Discovery Bay 2612

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  29. $102 to $186/night

    Discovery Bay 1602

    Discovery Bay 1602

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  30. $143 to $220/night

    Discovery Bay 2511

    Discovery Bay 2511

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  31. $110 to $203/night

    Discovery Bay 3719

    Discovery Bay 3719

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  32. $151 to $244/night

    Discovery Bay 2311

    Discovery Bay 2311

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  33. $85 to $151/night

    Discovery Bay 2907

    Discovery Bay 2907

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  34. $88 to $157/night

    Discovery Bay 4012

    Discovery Bay 4012

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  35. $79 to $139/night

    Discovery Bay 2016

    Discovery Bay 2016

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  36. $85 to $151/night

    Discovery Bay 3707

    Discovery Bay 3707

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  37. $151 to $244/night

    Discovery Bay 3604

    Discovery Bay 3604

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  38. $102 to $186/night

    Discovery Bay 1309

    Discovery Bay 1309

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  39. $82 to $157/night

    Discovery Bay 3505

    Discovery Bay 3505

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  40. $102 to $186/night

    Discovery Bay 1613

    Discovery Bay 1613

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  41. $143 to $220/night

    Discovery Bay 1201

    Discovery Bay 1201

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  42. $110 to $203/night

    Discovery Bay 2502

    Discovery Bay 2502

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  43. $82 to $145/night

    Discovery Bay 3720

    Discovery Bay 3720

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  44. $102 to $186/night

    Discovery Bay 2003

    Discovery Bay 2003

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  45. $82 to $145/night

    Discovery Bay 1815

    Discovery Bay 1815

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  46. $110 to $203/night

    Discovery Bay 1202

    Discovery Bay 1202

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  47. $88 to $157/night

    Discovery Bay 3220

    Discovery Bay 3220

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  48. $151 to $501/night

    Discovery Bay 1311

    Discovery Bay 1311

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  49. $102 to $186/night

    Discovery Bay 3619

    Discovery Bay 3619

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  50. $158 to $286/night

    Mountain & Golf Course Views! 3 Bed/3 Bath

    Mountain & Golf Course Views! 3 Bed/3 Bath

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $138 to $415/night

    Ilikai Marina 1094

    Ilikai Marina 1392

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  52. $157 to $430/night

    Ilikai Tower 931

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  53. $290 to $789/night

    Ilikai Tower 409

    Ilikai Tower 409

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  54. $99 to $313/night

    Ilikai Marina 1895

    Ilikai Marina 1893

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  55. $157 to $411/night

    Ilikai Tower 839

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  56. $161 to $455/night

    Ilikai Tower 634

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  57. $232 to $679/night

    Ilikai Tower 525

    Ilikai Tower 525

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  58. $138 to $396/night

    Ilikai Tower 613

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  59. $133 to $407/night

    Ilikai Tower 936

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  60. $145 to $368/night

    Ilikai Tower 735

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  61. $161 to $397/night

    Ilikai Tower 1642

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  62. $115 to $1,443/night

    Ilikai Marina 682

    Ilikai Marina 1392

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  63. $290 to $991/night

    Ilikai Tower 1744

    Ilikai Tower 1744

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  64. $348 to $974/night

    Ilikai Tower 1934

    Ilikai Tower 1934

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  65. $145 to $415/night

    Ilikai Tower 1812

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  66. $93 to $296/night

    Ilikai Marina 1781

    Ilikai Marina 1893

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  67. $232 to $1,074/night

    Ilikai Tower 943

    Ilikai Tower 943

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  68. $145 to $415/night

    Ilikai Tower 527

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  69. $154 to $455/night

    Ilikai Tower 814

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  70. $133 to $399/night

    Ilikai Tower 701

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  71. $128 to $349/night

    Ilikai Tower 2121

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  72. $157 to $430/night

    Ilikai Tower 633

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  73. $150 to $484/night

    Ilikai Tower 2136

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  74. $70 to $242/night

    Ilikai Marina 1889

    Ilikai Marina 1893

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  75. $348 to $1,003/night

    Ilikai Tower 2612

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  76. $133 to $358/night

    Ilikai Tower 618

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  77. $133 to $340/night

    Ilikai Tower 916

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  78. $133 to $369/night

    Ilikai Tower 405

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  79. $161 to $430/night

    Ilikai Tower 404

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  80. $104 to $328/night

    Ilikai Marina 1893

    Ilikai Marina 1893

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  81. $81 to $273/night

    Ilikai Marina 1495

    Ilikai Marina 1893

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  82. $145 to $361/night

    Ilikai Tower 333

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  83. $161 to $455/night

    Ilikai Tower 1920

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  84. $161 to $484/night

    Ilikai Marina 1392

    Ilikai Marina 1392

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  85. $133 to $390/night

    Ilikai Tower 827

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  86. $161 to $407/night

    Ilikai Tower 420

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  87. $223 to $258/night

    KEALIA RESORT, #609**

    KEALIA RESORT, #609**

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
  88. $152 to $286/night

    Exceptional Value for Family! Beautiful Views & Sunsets!

    Exceptional Value for Family! Beautiful Views & Suns...

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $409 to $810/night

    Pili Mai 6K

    Pili Mai 6K

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  90. $405 to $499/night

    Wilikeiki

    Wilikeiki

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  91. $1,870 to $2,494/night

    Wilikoki House

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  92. $208 to $336/night

    Honokeana Cove 103

    Honokeana Cove 103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  93. $173 to $400/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. $160 to $463/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $218 to $271/night

    New Listing! Hawaiian Experience- Walk to Two Step

    New Listing! Hawaiian Experience- Walk to Two Step

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  96. $166 to $465/night

    New Listing! “Kona Sunset Hale” w/ Ocean Views

    New Listing! “Kona Sunset Hale” w/ Ocean Views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  97. $96 to $359/night

    Waikiki Grand Condominium 705 *Legal Vacation Rental

    Waikiki Grand Condominium 705 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $255 to $383/night

    Luana Kai #B-313

    Luana Kai #B-313

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $923 to $2,945/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  100. $252 to $675/night

    Waikoloa Villas F-100

    Waikoloa Villas F-100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub