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. $701 to $3,474/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $110 to $398/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $132 to $388/night

    Napili Shores D229 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $408 to $815/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $241 to $729/night

    Napili Shores A106 Studio Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $217 to $685/night

    Papakea C207 Studio Condo

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $263 to $794/night

    Mahana 604 Oceanfront 1BD/1BA

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $229 to $691/night

    Maui Kai 805 Ocean View 1 bedroom/1 bath

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $217 to $685/night

    Papakea H107 AC, King Bed, Ground Corner Unit

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $202 to $610/night

    Napili Shores G154 Ocean View Studio

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $223 to $672/night

    Maui Kai 908 Oceanfront 1 Bedroom

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $104 to $489/night

    Big Island Kona Magic Sands 113

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $520 to $1,689/night

    Honua Kai Hokulani 310

    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. $252 to $886/night

    Big Island Sea Village 3212

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $541 to $1,833/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $287 to $1,130/night

    Menehune Shores 102

    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. $659 to $2,025/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $90 to $398/night

    Kaanapali Shores 742 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $361 to $1,118/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $270 to $951/night

    Whaler 616 Studio Condo

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $212 to $644/night

    Papakea L207 Ocean Front 1 Bedroom

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $1,220 to $4,156/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 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. $218 to $712/night

    Big Island Royal Sea Cliff 401

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $154 to $576/night

    Cliffs 5205

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $721 to $2,362/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $125 to $685/night

    Maui Kai 1005 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $361 to $1,118/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $138 to $521/night

    Big Island Kona Islander #341

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $387 to $1,061/night

    Sands Of Kahana 315 2Bd/2Ba Oceanfront

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $294 to $888/night

    Papakea K406 OceanView 2 Bedroom 2 bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations