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. $477 to $2,175/night

    Wailea Ekahi 26A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $461 to $1,510/night

    Kapalua Ridge Villas-#2212

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $335 to $943/night

    Big Island Na Hale O Keauhou E3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  11. $2,958 to $11,468/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  14. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  15. $1,202 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $394 to $1,050/night

    Makana Kai Hale

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,220 to $4,156/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $404 to $737/night

    Big Island Kona Nalu 203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $172 to $521/night

    Big Island Keauhou Surf & Racquet 22

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $362 to $467/night

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $721 to $2,362/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $981 to $4,337/night

    Ho'olei 21-3

    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. $865 to $3,810/night

    Ho'olei 12-4

    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. $987 to $4,542/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $659 to $2,027/night

    Noelani 307

    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. $213 to $316/night

    Kamaole Sands 8-101

    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. $1,349 to $1,609/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $274 to $696/night

    Kapalua Golf Villas 21T1

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $3,035 to $11,631/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $701 to $3,474/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $357 to $1,044/night

    Kauai Regency at Poipu Kai #711

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $420 to $735/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $281 to $1,306/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $935 to $1,767/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $576 to $1,374/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $353 to $1,387/night

    Kamaole Nalu 402

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $362 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $866 to $3,870/night

    Ho'olei 24-6

    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. $329 to $883/night

    Kapalua Bay Villas 37G1

    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. $750 to $3,970/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $179 to $647/night

    Kihei Akahi D-210

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $303 to $630/night

    Kona Sunset House at Walua

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $145 to $536/night

    Breezy 12th Floor Waikiki Condo with FREE Parking

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $127 to $448/night

    Deluxe Ocean View Condo 2 Queen Beds in Waikiki, FREE Pa...

    1 Bedroom BathroomSleeps 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. $300 to $1,243/night

    Wailea Ekahi 45A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $923 to $4,451/night

    Ho'olei 24-4

    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. $767 to $2,974/night

    Wailea Beach Villa H102

    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. $923 to $3,670/night

    Ho'olei 55-3

    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. $220 to $681/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $466 to $1,650/night

    Kauai Kiahuna Plantation #64

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $283 to $763/night

    Mahina Surf 111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations