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. $1,125 to $4,495/night

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $348 to $1,525/night

    He'eia Bay Hale

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $535 to $1,250/night

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  7. $283 to $330/night

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $318 to $363/night

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $346 to $469/night

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $296 to $416/night

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $354 to $524/night

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  17. $281 to $398/night

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,797 to $2,217/night

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $274 to $521/night

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
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  23. $549/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $420 to $480/night

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $269 to $324/night

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $348 to $430/night

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $355 to $534/night

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $314 to $415/night

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $320 to $420/night

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $331 to $548/night

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $344 to $449/night

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $348 to $438/night

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $394 to $877/night

    Ilikai 1243

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $296 to $521/night

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $664 to $1,668/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $188 to $443/night

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $333 to $464/night

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $641 to $992/night

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $576/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $336 to $444/night

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 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. $641 to $2,536/night

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $320 to $475/night

    Kaleialoha 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $256 to $423/night

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $359 to $456/night

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $296 to $433/night

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $294 to $436/night

    Kihei Alii Kai A207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $294 to $400/night

    Kauhale Makai 203

    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. $381 to $551/night

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $445 to $491/night

    Eldorado A203

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $445 to $569/night

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $309 to $446/night

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $348 to $435/night

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $375 to $475/night

    Kihei Resort 202

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $301 to $436/night

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,395/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,679/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $278 to $399/night

    Kihei Akahi C-616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $306 to $419/night

    Kona Bay View House

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations