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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. $987 to $4,542/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  3. $300 to $868/night

    Sugar Beach Resort 328

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  5. $375 to $1,266/night

    Grand Champions 30

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $318 to $1,356/night

    Maui Banyan G302

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  11. $1,443 to $5,169/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  13. $213 to $316/night

    Kamaole Sands 8-101

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  15. $272 to $808/night

    Sugar Beach Resort 409

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $370 to $1,129/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $467 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $659 to $879/night

    Kona Bay Hale

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $3,035 to $11,631/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $163 to $624/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $1,038 to $5,013/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $1,038 to $3,879/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $281 to $1,306/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $265 to $1,113/night

    Grand Champions 60

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $236 to $687/night

    Hale Mahina #B101

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $394 to $735/night

    Hale Mahina #B403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $473 to $587/night

    Kaanapali Shores #159

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $683 to $1,063/night

    Kaanapali Shores #160

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $629 to $992/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $198 to $523/night

    Maui Kaanapali Villas #E290

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $415 to $878/night

    Maui Kaanapali Villas #A317

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $415 to $515/night

    Maui Kaanapali Villas #A517

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $341 to $570/night

    Papakea #E207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $373 to $627/night

    Papakea #G103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $425 to $648/night

    Papakea #A201

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $263 to $597/night

    Maui Kaanapali Villas #B247

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $446 to $878/night

    Maui Kaanapali Villas #A512

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $394 to $741/night

    Papakea #F407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,950 to $2,249/night

    Puuwai Alii Estate

    5 Bedrooms5.5 BathroomsSleeps 8
    7 nights minstay
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $283 to $1,101/night

    Grand Champions 138

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $250 to $678/night

    Kamaole Sands 6-104

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $145 to $491/night

    Spacious 14th Floor Corner Suite, Partial Diamond Head a...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $268 to $1,076/night

    Grand Champions 36

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $520 to $2,059/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $204 to $557/night

    Kamaole Sands 8-206

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $329 to $1,780/night

    Grand Champions 170

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $808 to $2,974/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $231 to $959/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $170 to $254/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $308 to $730/night

    Villas of Kamalii 47

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $277 to $469/night

    Emmalani Court 312

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $229 to $475/night

    Pono Kai H204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $373 to $562/night

    Colony Villas at Waikoloa Beach Resort #1305

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations