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
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  2. CONDOMINIUM
    Kahana Manor 410

    Kahana Manor 410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $324/night

  3. CONDOMINIUM
    Pacific Shores B406

    Pacific Shores B406

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $318/night

  4. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club#37

    Keauhou Kona Surf & Racquet Club#37

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $222 to $228/night

  5. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $448/night

  6. CONDOMINIUM
    Maui Kai 201

    Maui Kai 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $675/night

  7. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $361 to $749/night

  8. CONDOMINIUM
    Mahana 519

    Mahana 519

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $410 to $1,336/night

  9. 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

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

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $397 to $977/night

  11. CONDOMINIUM
    Kaanapali Shores 546

    Kaanapali Shores 546

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $166 to $441/night

  12. 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

  13. CONDOMINIUM
    Emmalani Court #525

    Emmalani Court #525

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  14. 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

  15. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $264/night

  16. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $345/night

  17. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $193 to $306/night

  18. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  19. CONDOMINIUM
    Maui Vista 2211

    Maui Vista 2211

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $388/night

  20. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $168 to $374/night

  21. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $394/night

  22. 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

  23. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $239 to $348/night

  24. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  25. 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

  26. CONDOMINIUM
    Kihei Kai Nani 373

    Kihei Kai Nani 373

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $335/night

  27. 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

  28. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  29. HOUSE
    Plantation Cottage

    Plantation Cottage

    Hanalei, HI

    FREE CANCELLATION

    $392 to $523/night

  30. 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

  31. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    FREE CANCELLATION

    $163 to $239/night

  32. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  33. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $284/night

  34. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $324/night

  35. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $321/night

  36. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $125 to $275/night

  37. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $264/night

  38. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $675/night

  39. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $370/night

  40. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  41. 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

  42. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $498/night

  43. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $498/night

  44. 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

  45. CONDOMINIUM
    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $484/night

  46. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $358/night

  47. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $134 to $239/night

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

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

  49. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  50. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  51. CONDOMINIUM
    Maui Banyan Q306

    Maui Banyan Q306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $431/night

  52. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $304/night

  53. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Pool
    FREE CANCELLATION

    $324 to $534/night

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

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  55. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $500/night

  56. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $213 to $624/night

  57. 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

  58. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  59. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  60. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,938 to $4,750/night

  61. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $158 to $239/night

  62. 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

  63. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $306/night

  64. CONDOMINIUM
    Kaanapali Shores 836

    Kaanapali Shores 836

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $330/night

  65. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  66. CONDOMINIUM
    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $174 to $731/night

  67. CONDOMINIUM
    Nihilani 28C

    Nihilani 28C

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $374/night

  68. CONDOMINIUM
    Maalaea Banyans 203

    Maalaea Banyans 203

    Wailuku, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $288/night

  69. CONDOMINIUM
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $345/night

  70. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $358/night

  71. CONDOMINIUM
    Pacific Shores B414

    Pacific Shores B414

    Kihei, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  72. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $183 to $660/night

  73. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $415/night

  74. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $193 to $312/night

  75. CONDOMINIUM
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $298 to $916/night

  76. CONDOMINIUM
    Eldorado A203

    Eldorado A203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $480/night

  77. 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

  78. 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

  79. 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

  80. 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

  81. CONDOMINIUM
    PentHouse 701

    PentHouse 701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $275/night

  82. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Pool
    FREE CANCELLATION

    $174 to $420/night

  83. 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

  84. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  85. CONDOMINIUM
    Aina Nalu G204

    Aina Nalu G204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $466/night

  86. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $416 to $1,291/night

  87. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $401/night

  88. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $435/night

  89. CONDOMINIUM
    Hale Ono Loa 416

    Hale Ono Loa 416

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $150 to $360/night

  90. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $229 to $365/night

  91. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $484/night

  92. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $353/night

  93. HOUSE
    Chung Cottage

    Chung Cottage

    Hanalei, HI

    FREE CANCELLATION

    $249 to $312/night

  94. CONDOMINIUM
    HBR1207-08

    HBR1207-08

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $405/night

  95. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $279 to $760/night

  96. CONDOMINIUM
    Hanalei Bay Villas #16

    Hanalei Bay Villas #16

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  97. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $149 to $405/night

  98. HOUSE
    Ohana House

    Ohana House

    Hanalei, HI

    FREE CANCELLATION

    $499 to $562/night

  99. HOUSE
    Malapua

    Malapua

    Hanalei, HI

    FREE CANCELLATION

    $748 to $1,060/night

  100. HOUSE
    Hale Koaniani

    Hale Koaniani

    Wainiha, HI

    FREE CANCELLATION

    $717 to $904/night