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. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  2. $1,870 to $2,494/night

    Wilikoki House

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  3. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  4. $1,066 to $1,459/night

    MAKENA SURF RESORT, #G-304

    MAKENA SURF RESORT, #G-304

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  5. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  8. $1,000 to $2,898/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  9. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  10. $897 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  11. $858 to $2,575/night

    Honua Kai-Konea #925

    Honua Kai-Konea #925

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $813 to $1,219/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  13. $781 to $1,219/night

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  14. $781 to $1,219/night

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  15. $781 to $1,219/night

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  16. $781 to $1,219/night

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  17. $775 to $1,094/night

    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  18. $775 to $1,094/night

    MAKENA SURF RESORT, #F-209

    MAKENA SURF RESORT, #F-209

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  19. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  20. $775 to $1,094/night

    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  21. $775 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  22. $755 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $740 to $2,021/night

    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  24. $719 to $1,410/night

    Nai'a Hale

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  25. $717 to $904/night

    Hale Koaniani

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  26. $706 to $1,038/night

    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  27. $706 to $1,038/night

    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  28. $706 to $1,038/night

    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  29. $689 to $841/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $668 to $846/night

    Ali'i Point #5 Oceanfront

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  31. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  32. $656 to $875/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  33. $656 to $906/night

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  34. $644 to $919/night

    Mahana 501

    Mahana 501

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  36. $623 to $748/night

    Hale Kalani

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  37. $608 to $790/night

    Hale Huna Kai- Oceanfront

    Hale Huna Kai- Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  38. $608 to $846/night

    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. $594 to $969/night

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    2 Bedrooms2.25 BathroomsSleeps 6
    4 nights minstay
    Pool
  41. $594 to $1,063/night

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  42. $583 to $724/night

    ROYAL MAUIAN, #102^

    ROYAL MAUIAN, #102^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  43. $583 to $724/night

    ROYAL MAUIAN, #302

    ROYAL MAUIAN, #302

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  44. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  45. $580 to $1,015/night

    Kahana Outrigger #2B1

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $577 to $679/night

    MENEHUNE SHORES, #510**^

    MENEHUNE SHORES, #510**^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  47. $574 to $1,347/night

    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  48. $563 to $781/night

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  49. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  50. $563 to $1,125/night

    Kahana Reef #322

    Kahana Reef #322

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  51. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  52. $557 to $651/night

    Keauhou Kona Surf and Racquet Club 5-304

    Keauhou Kona Surf and Racquet Club 5-304

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  53. $542 to $555/night

    Hale Pahukoa

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  54. $531 to $969/night

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  55. $526 to $860/night

    Papakea K-402

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $516 to $620/night

    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $513 to $1,789/night

    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  59. $510 to $565/night

    Kaanapali Shores 725

    Kaanapali Shores 725

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $506 to $563/night

    Sands Of Kahana 234

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  61. $506 to $563/night

    Sands Of Kahana 215

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  62. $506 to $563/night

    Sands Of Kahana 315

    Sands Of Kahana 315

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  63. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  64. $504 to $896/night

    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  65. $504 to $896/night

    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  66. $503 to $649/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $501 to $1,093/night

    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  68. $501 to $619/night

    Sands of Kahana 366

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  69. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  70. $494 to $781/night

    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua Bay Villa 30B1 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  71. $488 to $560/night

    MENEHUNE SHORES, #218^

    MENEHUNE SHORES, #218^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  72. $488 to $560/night

    MENEHUNE SHORES, #515

    MENEHUNE SHORES, #515

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  73. $487 to $1,183/night

    Sands of Kahana #292

    Sands of Kahana #292

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  75. $476 to $690/night

    Napili Point A9

    Napili Point A9

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $469 to $680/night

    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $463 to $610/night

    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. $455 to $1,035/night

    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  79. $448 to $785/night

    MAKENA SURF RESORT, #A-101

    MAKENA SURF RESORT, #A-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  80. $448 to $702/night

    ROYAL MAUIAN, #518^

    ROYAL MAUIAN, #518^

    3 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool
  81. $445 to $467/night

    Keauhou Kona Surf & Racquet Club #5-303

    Keauhou Kona Surf & Racquet Club #5-303

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. $444 to $557/night

    Sands Of Kahana 275

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  83. $444 to $585/night

    Kona Makai 1-301

    Kona Makai 1-301

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $443 to $1,022/night

    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  85. $436 to $715/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $429 to $800/night

    Kaanapali Shores #160

    Kaanapali Shores #160

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $428 to $484/night

    Kahana Sunset A4

    Kahana Sunset A4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  88. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  89. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  90. $428 to $484/night

    Kahana Sunset A5

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  91. $428 to $484/night

    Kahana Sunset F4

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  92. $428 to $484/night

    Kahana Sunset F2

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  93. $426/night

    Kauhale Makai #411

    Kauhale Makai #411

    2 BedroomsBathroomsSleeps 4
    10 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $426 to $795/night

    Hale Ono Loa 109

    Hale Ono Loa 109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $426 to $619/night

    Ilikai #1743

    Ilikai #1743

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  96. $425 to $561/night

    ROYAL MAUIAN, #614

    ROYAL MAUIAN, #614

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  97. $422 to $663/night

    Puu Poa 403

    Puu Poa 403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $420 to $693/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $418 to $891/night

    Noelani 304 3bdrm 2.5 bath

    Noelani 304 3bdrm 2.5 bath

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  100. $418 to $653/night

    Kaanapali Shores 527

    Kaanapali Shores 527

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION