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. $563 to $744/night

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
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  3. $390 to $524/night

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  5. $257 to $304/night

    Sealodge G8

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  7. $238 to $275/night

    Sealodge J2

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
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  9. $238 to $275/night

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $246 to $311/night

    Black Sand Beach House

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  13. $139 to $158/night

    Maluhia Kahakai

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $134/night

    Paradise Cliff House

    2 BedroomsBathroomsSleeps 4
    31 nights minstay
    FREE CANCELLATION
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  17. $656 to $906/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
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  19. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $238 to $275/night

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  23. $257 to $304/night

    Sealodge E10

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $275 to $324/night

    Alii Kai 5301

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  27. $257 to $304/night

    Sealodge C7

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
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  29. $183 to $246/night

    Maui Sunset B110

    1 BedroomBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $246 to $315/night

    THE JEWEL BOX

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  33. $251 to $629/night

    Mahana 608

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $164 to $231/night

    Sea Village 1-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $17,975 to $27,561/night

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    6 nights minstay
    Pool Hot Tub
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  39. $257 to $300/night

    Alii Kai 3103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  41. $257 to $287/night

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  43. $257 to $304/night

    Sealodge J1

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
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  45. $257 to $361/night

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  47. $2,078 to $3,780/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
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  49. $251 to $340/night

    Lae Nani 333, Oceanview, Renovated and Gated

    1 Bedroom1.5  BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  51. $170 to $215/night

    Maalaea Kai 316

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  53. $310 to $404/night

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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