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
    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $341/night

  2. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  3. HOUSE
    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  4. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  5. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  6. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $322 to $769/night

  7. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $383/night

  8. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $202 to $480/night

  9. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $495/night

  10. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  11. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  12. CONDOMINIUM
    131

    131

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  13. CONDOMINIUM
    217

    217

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  14. CONDOMINIUM
    209

    209

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  15. CONDOMINIUM
    Kamaole Sands #2-306

    Kamaole Sands #2-306

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $347/night

  16. CONDOMINIUM
    Wailea Ekolu #503

    Wailea Ekolu #503

    Wailea, HI

    Pool
    FREE CANCELLATION

    $232 to $521/night

  17. CONDOMINIUM
    Kamaole Sands #5-414

    Kamaole Sands #5-414

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $429/night

  18. CONDOMINIUM
    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $406/night

  19. CONDOMINIUM
    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $331/night

  20. CONDOMINIUM
    Hale Mahina #B103

    Hale Mahina #B103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $478/night

  21. CONDOMINIUM
    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $447/night

  22. CONDOMINIUM
    Papakea #A105

    Papakea #A105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $459/night

  23. CONDOMINIUM
    Papakea #H103

    Papakea #H103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $580/night

  24. CONDOMINIUM
    Kaanapali Royal #A303

    Kaanapali Royal #A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $600/night

  25. CONDOMINIUM
    Papakea #C108

    Papakea #C108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $383/night

  26. CONDOMINIUM
    Mahana Resort #1017

    Mahana Resort #1017

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $606/night

  27. CONDOMINIUM
    Kaanapali Royal #C101

    Kaanapali Royal #C101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $284 to $600/night

  28. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  29. CONDOMINIUM
    Mahana Resort #1106

    Mahana Resort #1106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $638/night

  30. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $505/night

  31. CONDOMINIUM
    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $209 to $354/night

  32. CONDOMINIUM
    Lahaina Shores #531

    Lahaina Shores #531

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $447/night

  33. CONDOMINIUM
    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $331/night

  34. CONDOMINIUM
    Royal Kahana #319

    Royal Kahana #319

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $122 to $331/night

  35. CONDOMINIUM
    Kaanapali Shores #916

    Kaanapali Shores #916

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $284 to $706/night

  36. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  37. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  38. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  39. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  40. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  41. HOUSE
    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  42. CONDOMINIUM
    Island Surf #502

    Island Surf #502

    Kihei, HI

    Pool
    FREE CANCELLATION

    $189 to $451/night

  43. CONDOMINIUM
    Kamaole Sands #1-103

    Kamaole Sands #1-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $278/night

  44. CONDOMINIUM
    Waiohuli Beach Hale #B-108

    Waiohuli Beach Hale #B-108

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  45. CONDOMINIUM
    309

    309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $393/night

  46. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  47. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night

  48. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  49. CONDOMINIUM
    Hale Mahina #B403

    Hale Mahina #B403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $600/night

  50. CONDOMINIUM
    Royal Kahana #1211

    Royal Kahana #1211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $969/night

  51. CONDOMINIUM
    Maui Kaanapali Villas #A517

    Maui Kaanapali Villas #A517

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $365/night

  52. CONDOMINIUM
    Maui Kaanapali Villas #A317

    Maui Kaanapali Villas #A317

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $348/night

  53. CONDOMINIUM
    Valley Isle #707

    Valley Isle #707

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $145 to $273/night

  54. CONDOMINIUM
    Hololani #A-202

    Hololani #A-202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $532/night

  55. CONDOMINIUM
    Mahana Resort #906

    Mahana Resort #906

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $554/night

  56. CONDOMINIUM
    Lahaina Roads #204

    Lahaina Roads #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $447/night

  57. CONDOMINIUM
    Maui Banyan #B-204

    Maui Banyan #B-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $377/night

  58. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  59. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $347/night

  60. CONDOMINIUM
    Maui Kamaole #J-221

    Maui Kamaole #J-221

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $463/night

  61. CONDOMINIUM
    Kihei Akahi #C-217

    Kihei Akahi #C-217

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $242/night

  62. CONDOMINIUM
    Mahana Resort #617

    Mahana Resort #617

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $638/night

  63. CONDOMINIUM
    Mahana Resort #1107

    Mahana Resort #1107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $638/night

  64. CONDOMINIUM
    Maui Kaanapali Villas #B231

    Maui Kaanapali Villas #B231

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $331/night

  65. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $429 to $800/night

  66. CONDOMINIUM
    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $377/night

  67. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $347/night

  68. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  69. CONDOMINIUM
    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    Kapaa, HI

    Pool Hot Tub

    $311 to $386/night

  70. CONDOMINIUM
    Wailea Elua #207

    Wailea Elua #207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $464 to $725/night

  71. CONDOMINIUM
    Grand Champions #72

    Grand Champions #72

    Wailea, HI

    Pool
    FREE CANCELLATION

    $406 to $696/night

  72. HOUSE
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  73. HOUSE
    Junior Suite Oceanfront #702

    Junior Suite Oceanfront #702

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  74. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  75. CONDOMINIUM
    Kamaole Sands #4-408

    Kamaole Sands #4-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $406/night

  76. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  77. CONDOMINIUM
    Grand Champions #50

    Grand Champions #50

    Wailea, HI

    Pool
    FREE CANCELLATION

    $201 to $477/night

  78. CONDOMINIUM
    Kamaole Sands #2-301

    Kamaole Sands #2-301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $283 to $644/night

  79. CONDOMINIUM
    Palms at Wailea #305

    Palms at Wailea #305

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $306 to $715/night

  80. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    Wailea, HI

    Pool
    FREE CANCELLATION

    $302 to $726/night

  81. CONDOMINIUM
    Casa de Emdeko 337

    Casa de Emdeko 337

    Kailua-Kona, HI

    Pool

    $140 to $228/night

  82. CONDOMINIUM
    206

    206

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  83. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $579/night

  84. CONDOMINIUM
    Kihei Bay Vista #C-106

    Kihei Bay Vista #C-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  85. CONDOMINIUM
    Waiohuli Beach Hale #C-111

    Waiohuli Beach Hale #C-111

    Kihei, HI

    Pool
    FREE CANCELLATION

    $232 to $394/night

  86. CONDOMINIUM
    Valley Isle #1004

    Valley Isle #1004

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $414/night

  87. CONDOMINIUM
    Lahaina Shores #522

    Lahaina Shores #522

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $157 to $360/night

  88. CONDOMINIUM
    Valley Isle #508

    Valley Isle #508

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $767/night

  89. CONDOMINIUM
    Mahana Resort #1104

    Mahana Resort #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $606/night

  90. CONDOMINIUM
    Valley Isle #310

    Valley Isle #310

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $522/night

  91. CONDOMINIUM
    Mahana Resort #1217

    Mahana Resort #1217

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $354 to $606/night

  92. CONDOMINIUM
    Maui Kaanapali Villas #D271

    Maui Kaanapali Villas #D271

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $549/night

  93. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,558/night

  94. CONDOMINIUM
    Paki Maui #224

    Paki Maui #224

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $226 to $500/night

  95. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $481 to $1,167/night

  96. CONDOMINIUM
    Valley Isle #705

    Valley Isle #705

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $139 to $423/night

  97. CONDOMINIUM
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $493 to $1,467/night

  98. CONDOMINIUM
    no image

    Maui Kamaole #H-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $383/night

  99. CONDOMINIUM
    Island Surf #601A

    Island Surf #601A

    Kihei, HI

    Pool
    FREE CANCELLATION

    $103 to $174/night

  100. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $458/night