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. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  2. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,938 to $4,750/night

  3. CONDOMINIUM
    WAILEA ELUA, #1305^

    WAILEA ELUA, #1305^

    Wailea, Maui, HI

    Pool Hot Tub

    $1,761 to $2,076/night

  4. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Pool Hot Tub

    $1,635 to $2,364/night

  5. HOUSE
    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    Kihei, Maui, HI

    Hot Tub

    $1,458 to $2,694/night

  6. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  7. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    Pool Hot Tub

    $1,372 to $2,014/night

  8. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  9. CONDOMINIUM
    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    Wailea, Maui, HI

    Pool Hot Tub

    $931 to $1,459/night

  10. CONDOMINIUM
    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    Makena, Maui, HI

    Pool Hot Tub

    $855 to $1,319/night

  11. CONDOMINIUM
    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    Makena, Maui, HI

    Pool Hot Tub

    $855 to $1,319/night

  12. CONDOMINIUM
    MAKENA SURF RESORT, #B-204

    MAKENA SURF RESORT, #B-204

    Makena, Maui, HI

    Pool Hot Tub

    $841 to $1,319/night

  13. CONDOMINIUM
    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    Wailea, Maui, HI

    Pool Hot Tub

    $841 to $1,515/night

  14. CONDOMINIUM
    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    Wailea, Maui, HI

    Pool Hot Tub

    $785 to $1,347/night

  15. CONDOMINIUM
    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    Wailea, Maui,, HI

    Pool Hot Tub

    $785 to $1,347/night

  16. CONDOMINIUM
    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua, HI

    $781 to $1,219/night

  17. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  18. CONDOMINIUM
    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  19. CONDOMINIUM
    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    Makena, Maui, HI

    Pool Hot Tub

    $762 to $1,094/night

  20. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  21. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  22. CONDOMINIUM
    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  23. CONDOMINIUM
    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  24. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  25. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

  26. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $656 to $906/night

  27. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $656 to $875/night

  28. HOUSE
    WAILEA ELUA, #1309

    WAILEA ELUA, #1309

    Wailea, Maui, HI

    Pool Hot Tub

    $634 to $896/night

  29. CONDOMINIUM
    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    Wailea, Maui, HI

    Pool Hot Tub

    $616 to $1,065/night

  30. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,325/night

  31. HOUSE
    Hale Huna Kai- Oceanfront

    Hale Huna Kai- Oceanfront

    Kailua Kona, HI

    FREE CANCELLATION

    $608 to $790/night

  32. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $573 to $1,344/night

  33. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $571 to $1,789/night

  34. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  35. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  36. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $513 to $977/night

  37. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  38. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  39. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  40. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,789/night

  41. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,789/night

  42. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  43. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  44. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  45. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  46. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  47. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  48. CONDOMINIUM
    Kaanapali Alii 456

    Kaanapali Alii 456

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $499 to $1,624/night

  49. CONDOMINIUM
    WAILEA ELUA, #0202*

    WAILEA ELUA, #0202*

    Wailea, Maui, HI

    Pool Hot Tub

    $494 to $1,065/night

  50. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  51. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  52. CONDOMINIUM
    WAILEA ELUA, #0702

    WAILEA ELUA, #0702

    Wailea, Maui, HI

    Pool Hot Tub

    $482 to $1,009/night

  53. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,209/night

  54. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,673/night

  55. CONDOMINIUM
    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    Wailea, Maui, HI

    Pool Hot Tub

    $471 to $896/night

  56. CONDOMINIUM
    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    Wailea, Maui, HI

    Pool Hot Tub

    $471 to $896/night

  57. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  58. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  59. CONDOMINIUM
    WAILEA ELUA, #0307

    WAILEA ELUA, #0307

    Wailea, Maui, HI

    Pool Hot Tub

    $459 to $953/night

  60. CONDOMINIUM
    WAILEA ELUA, #1503

    WAILEA ELUA, #1503

    Wailea, Maui, HI

    Pool Hot Tub

    $459 to $953/night

  61. CONDOMINIUM
    WAILEA ELUA, #0105

    WAILEA ELUA, #0105

    Wailea, Maui, HI

    Pool Hot Tub

    $459 to $953/night

  62. CONDOMINIUM
    WAILEA ELUA, #0801*

    WAILEA ELUA, #0801*

    Wailea, Maui, HI

    Pool Hot Tub

    $459 to $953/night

  63. CONDOMINIUM
    WAILEA ELUA, #2010

    WAILEA ELUA, #2010

    Wailea, Maui, HI

    Pool Hot Tub

    $459 to $953/night

  64. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool Hot Tub

    $456 to $659/night

  65. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $572/night

  66. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $607/night

  67. CONDOMINIUM
    WAILEA ELUA, #2107*

    WAILEA ELUA, #2107*

    Wailea, Maui, HI

    Pool Hot Tub

    $448 to $897/night

  68. CONDOMINIUM
    WAILEA ELUA, #0902

    WAILEA ELUA, #0902

    Wailea, Maui, HI

    Pool Hot Tub

    $448 to $1,065/night

  69. CONDOMINIUM
    WAILEA ELUA, #2106

    WAILEA ELUA, #2106

    Wailea, Maui, HI

    Pool Hot Tub

    $448 to $897/night

  70. CONDOMINIUM
    WAILEA ELUA, #2003

    WAILEA ELUA, #2003

    Wailea, Maui, HI

    Pool Hot Tub

    $448 to $823/night

  71. CONDOMINIUM
    Sands Of Kahana 275

    Sands Of Kahana 275

    Lahaina, HI

    Pool Hot Tub

    $444 to $557/night

  72. COTTAGE
    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    Kamuela, HI

    FREE CANCELLATION

    $442 to $1,018/night

  73. CONDOMINIUM
    WAILEA ELUA, #0802

    WAILEA ELUA, #0802

    Wailea, Maui, HI

    Pool Hot Tub

    $437 to $953/night

  74. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $432 to $1,499/night

  75. COTTAGE
    Moloa'a Bay Cottage

    Moloa'a Bay Cottage

    Anahola, HI

    $430 to $515/night

  76. CONDOMINIUM
    Kahana Sunset A4

    Kahana Sunset A4

    Lahaina, HI

    Pool

    $428 to $484/night

  77. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  78. CONDOMINIUM
    Kahana Sunset A5

    Kahana Sunset A5

    Lahaina, HI

    Pool

    $428 to $484/night

  79. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  80. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  81. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  82. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  83. CONDOMINIUM
    WAILEA ELUA, #0302

    WAILEA ELUA, #0302

    Wailea, Maui, HI

    Pool Hot Tub

    $425 to $834/night

  84. HOUSE
    Puu Poa 403

    Puu Poa 403

    Princeville, HI

    Pool

    $422 to $663/night

  85. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $419 to $740/night

  86. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  87. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $416 to $1,291/night

  88. CONDOMINIUM
    Puu Poa 406

    Puu Poa 406

    Princeville, HI

    Pool

    $416 to $512/night

  89. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  90. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  91. CONDOMINIUM
    Mahana 519

    Mahana 519

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $410 to $1,336/night

  92. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  93. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,383/night

  94. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,093/night

  95. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,209/night

  96. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    Kapolei, HI

    Pool Hot Tub

    $408 to $977/night

  97. CONDOMINIUM
    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua, HI

    Pool

    $406 to $781/night

  98. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,209/night

  99. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $397 to $977/night

  100. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night