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. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
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  3. $1,202 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
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  5. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,126 to $4,236/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $1,038 to $5,013/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $987 to $4,528/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $981 to $4,337/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $961 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
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  19. $936 to $2,531/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    3 nights minstay
    Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $923 to $4,451/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $923 to $3,670/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $923 to $4,087/night

    Ho'olei 24-1

    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. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $866 to $3,860/night

    Ho'olei 24-6

    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. $802 to $3,792/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $716 to $2,130/night

    Wailea Elua 2109

    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. $656 to $2,986/night

    Polo Beach Club 107

    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. $577 to $1,626/night

    Big Island Holua Kai 111

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $569 to $2,093/night

    Big Island Waiulaula at Mauna Kea J201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $549 to $1,381/night

    Big Island Holua Kai 7066

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $388 to $457/night

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $379 to $1,030/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $364 to $1,864/night

    Big Island Fairways at Mauna Lani 1705

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $363 to $1,094/night

    Residences at Napili Bay B7 3 Bedroom

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $362 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $362 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $329 to $1,426/night

    Big Island Golf Villas J23

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $316 to $791/night

    Hale Iolani

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $300 to $1,228/night

    Big Island Fairways at Mauna Lani 1701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $286 to $1,233/night

    Big Island Na Hale O Keauhou F6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $278 to $336/night

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $278 to $336/night

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $267 to $1,018/night

    Big Island Waikoloa Beach Villas N22

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $260 to $1,029/night

    Big Island Waikoloa Colony Villas 2404

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $252 to $1,017/night

    Big Island Awamoa Hale

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $243 to $396/night

    Nihilani 11A

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $227 to $651/night

    Big Island Keauhou Gardens 1201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $198 to $630/night

    Holualoa Bay Villas#105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $191 to $669/night

    37th Floor Condo with Sweeping Ocean Views & Free pa...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $175 to $630/night

    Kona Plaza 215

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $173 to $655/night

    Standard Ocean View Condo- 36th Floor, Free parking &...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $172 to $319/night

    Vacation Home in Ko Olina Resort

    2 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. $164 to $596/night

    Excellent Diamond Head View Condo- Remodeled, Free Parki...

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $164 to $596/night

    High Level Waikiki Condo- Enjoy Ocean Views From Your Pr...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $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
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $164 to $655/night

    Deluxe Condo with Pool View, Free Parking & Wi-Fi

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $164 to $596/night

    Deluxe Ocean View Condo on 31st Floor- Free Parking &...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $160 to $596/night

    Beautifully Renovated 32nd Floor Deluxe Ocean View Waiki...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $156 to $525/night

    Kona Plaza#210

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $149 to $550/night

    Deluxe 21st Floor Corner Condo with Diamond Head Views, ...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $149 to $419/night

    Malia Kai#19

    1 Bedroom1.5  BathroomSleeps 4
    3 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $149 to $522/night

    Updated 22nd Floor Waikiki Condo- Free parking & WiF...

    1 Bedroom BathroomSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $145 to $536/night

    Breezy 12th Floor Waikiki Condo with FREE Parking

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $145 to $536/night

    Waikiki Banyan High Level Condo with Private Lanai

    1 Bedroom BathroomSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $145 to $492/night

    Fully Equipped 23rd Floor Condo at the Waikiki Banyan

    1 Bedroom BathroomSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $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
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $145 to $565/night

    Gorgeous High Rise Waikiki Condo with Ocean and Diamond ...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $140 to $426/night

    Big Island Kona Mansions 110C

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $136 to $521/night

    Light & Airy 8th Floor Ocean View Condo with Lanai a...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $136 to $480/night

    19th Floor Condo with Lanai & Sea Views- FREE Parkin...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $136 to $411/night

    Royal Kahana 119 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $136 to $479/night

    21st Floor Condo With View of Ko'olau Mountains and...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $131 to $525/night

    Kona Plaza#202

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $118 to $398/night

    Kaanapali Shores 422 1 Bedroom Condo

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