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. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  2. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  3. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  4. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    FREE CANCELLATION

    $304 to $467/night

  5. CONDOMINIUM
    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  6. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  7. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  8. CONDOMINIUM
    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  9. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  10. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  11. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  12. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $435/night

  13. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $415/night

  14. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  15. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  16. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  17. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  18. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  19. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  20. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  21. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  22. 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

  23. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  24. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  25. 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

  26. 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

  27. 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

  28. 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

  29. 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

  30. 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

  31. 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

  32. 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

  33. 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

  34. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  35. 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

  36. 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

  37. 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

  38. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

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

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $397 to $977/night

  40. 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

  41. 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

  42. 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

  43. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $704/night

  44. 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

  45. 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

  46. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $1,059/night

  47. CONDOMINIUM
    Hololani A204

    Hololani A204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $199 to $425/night

  48. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  49. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  50. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $484/night

  51. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $199 to $466/night

  52. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $149 to $405/night

  53. CONDOMINIUM
    Kaanapali Royal Q101

    Kaanapali Royal Q101

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $259 to $729/night

  54. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $1,016/night

  55. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $1,016/night

  56. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $279 to $760/night

  57. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $406/night

  58. CONDOMINIUM
    Kaanapali Shores 836

    Kaanapali Shores 836

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $330/night

  59. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $155 to $531/night

  60. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  61. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $498/night

  62. CONDOMINIUM
    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $359/night

  63. CONDOMINIUM
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $345/night

  64. CONDOMINIUM
    Kahana Sunset B3B

    Kahana Sunset B3B

    Lahaina, HI

    Pool

    $186 to $214/night

  65. CONDOMINIUM
    Kahana Sunset B5B

    Kahana Sunset B5B

    Lahaina, HI

    Pool

    $214 to $270/night

  66. CONDOMINIUM
    Kahana Sunset B6

    Kahana Sunset B6

    Lahaina, HI

    Pool

    $309 to $366/night

  67. CONDOMINIUM
    Kahana Sunset B7

    Kahana Sunset B7

    Lahaina, HI

    Pool

    $309 to $366/night

  68. CONDOMINIUM
    Kahana Sunset B8

    Kahana Sunset B8

    Lahaina, HI

    Pool

    $309 to $366/night

  69. CONDOMINIUM
    Kahana Sunset C 3

    Kahana Sunset C 3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $394/night

  70. CONDOMINIUM
    Kahana Sunset C1C

    Kahana Sunset C1C

    Lahaina, HI

    Pool

    $214 to $270/night

  71. CONDOMINIUM
    Kahana Sunset C4

    Kahana Sunset C4

    Lahaina, HI

    Pool

    $219 to $276/night

  72. CONDOMINIUM
    Kahana Sunset C5

    Kahana Sunset C5

    Lahaina, HI

    Pool

    $276 to $332/night

  73. CONDOMINIUM
    Kahana Sunset C7

    Kahana Sunset C7

    Lahaina, HI

    Pool

    $276 to $332/night

  74. CONDOMINIUM
    Kahana Sunset D10

    Kahana Sunset D10

    Lahaina, HI

    Pool

    $253 to $309/night

  75. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $276 to $332/night

  76. CONDOMINIUM
    Kahana Sunset D6

    Kahana Sunset D6

    Lahaina, HI

    Pool

    $276 to $332/night

  77. CONDOMINIUM
    Kahana Sunset D7

    Kahana Sunset D7

    Lahaina, HI

    Pool

    $276 to $332/night

  78. CONDOMINIUM
    Kahana Sunset D8

    Kahana Sunset D8

    Lahaina, HI

    Pool

    $276 to $332/night

  79. CONDOMINIUM
    Kahana Sunset D9

    Kahana Sunset D9

    Lahaina, HI

    Pool

    $276 to $332/night

  80. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $239 to $348/night

  81. CONDOMINIUM
    Kahana Sunset E6

    Kahana Sunset E6

    Lahaina, HI

    Pool

    $276 to $332/night

  82. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  83. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  84. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  85. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  86. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  87. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $359/night

  88. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $443/night

  89. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $168 to $374/night

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

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua, HI

    Pool

    $406 to $781/night

  91. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $656 to $875/night

  92. CONDOMINIUM
    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua, HI

    Pool

    $369 to $594/night

  93. CONDOMINIUM
    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $633/night

  94. CONDOMINIUM
    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $484/night

  95. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $401/night

  96. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $264/night

  97. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  98. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $302 to $326/night

  99. CONDOMINIUM
    Kulakane 301

    Kulakane 301

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $225 to $531/night

  100. CONDOMINIUM
    Kulakane 307

    Kulakane 307

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $531/night