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. $253 to $311/night

    Leinaala #401

    Leinaala #401

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  2. $428 to $543/night

    Grand Champions #118

    Grand Champions #118

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $297 to $396/night

    Sugar Beach #302

    Sugar Beach #302

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $196 to $284/night

    Unit 108

    Unit 108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  5. $235 to $317/night

    329

    329

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  6. $241 to $279/night

    Maui Vista #1120

    Maui Vista #1120

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  7. $290 to $332/night

    Kamaole Sands #01-302

    Kamaole Sands #01-302

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $163 to $327/night

    Kona Makai 2-102

    Kona Makai 2-102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $260/night

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    1 BedroomBathroomsSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $468 to $594/night

    Kapalua Golf Villas #12T5

    Kapalua Golf Villas #12T5

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  12. $341 to $434/night

    Maui Kamaole #h-104

    Maui Kamaole #h-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $102 to $186/night

    Discovery Bay 1309

    Discovery Bay 1309

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  14. $297 to $396/night

    Sugar Beach #301

    Sugar Beach #301

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $261 to $326/night

    Maui Parkshore #202

    Maui Parkshore #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  16. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $294 to $494/night

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  18. $339 to $861/night

    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  19. $156/night

    Turtle Bay 126 West Budget NUC 90-TVU-0538

    Turtle Bay 126 West Budget NUC 90-TVU-0538

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $302 to $354/night

    Unit 311

    Unit 311

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  21. $188 to $258/night

    113

    113

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $211 to $235/night

    Cliffs 6201

    Cliffs 6201

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $525 to $869/night

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  24. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $241 to $279/night

    Maui Vista #3301

    Maui Vista #3301

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  26. $225 to $267/night

    Kihei Bay Vista #C-202

    Kihei Bay Vista #C-202

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $267 to $326/night

    Kauhale Makai #331

    Kauhale Makai #331

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $235 to $296/night

    Kihei Akahi #D-608

    Kihei Akahi #D-608

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  29. $271 to $331/night

    Pali Ke Kua 130

    Pali Ke Kua 130

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $113 to $163/night

    KV1107A 2450 Prince Edward St Honolulu THTH-CTOM(YS)-02M-ACH

    KV1107A 2450 Prince Edward St Honolulu THTH-CTOM(YS)-02M...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  31. $198 to $326/night

    Kona Isle E23

    Kona Isle E23

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  32. $623 to $748/night

    Hale Kalani

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  33. $156 to $250/night

    Ilikai 1507

    Ilikai 1507

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $338 to $576/night

    Ilikai 526

    Ilikai 526

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  36. $531 to $969/night

    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua Bay Villa 32B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  37. $218 to $296/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  38. $211 to $259/night

    Cliffs 5201

    Cliffs 5201

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  40. $129 to $359/night

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $119 to $158/night

    Aloha Surf 1507 Condominium

    Aloha Surf 1507 Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $141/night

    Bamboo 505 Condominium

    Bamboo 505 Condominium

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  43. $1,103/night

    Diamond Head Beach Hotel Rooftop 1402

    Diamond Head Beach Hotel Rooftop 1402

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  44. $428 to $546/night

    Maui Kamaole #C-209

    Maui Kamaole #C-209

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $334 to $444/night

    Sugar Beach #334

    Sugar Beach #334

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $274 to $465/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  47. $188 to $258/night

    205

    205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $269 to $409/night

    276

    276

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  49. $197 to $264/night

    Nani Kai Hale # 302

    Nani Kai Hale # 302

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  50. $141 to $250/night

    Ilikai Marina 484

    Ilikai Marina 484

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  51. $152 to $300/night

    Ilikai 1308

    Ilikai 1308

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $344 to $460/night

    Kihei Surfside #212

    Kihei Surfside #212

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  53. $428 to $546/night

    Maui Kamaole #j-214

    Maui Kamaole #j-214

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $259 to $301/night

    Pali Ke Kua 115

    Pali Ke Kua 115

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $141 to $208/night

    Nani Kai Hale # 601

    Nani Kai Hale # 601

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  56. $390 to $488/night

    Maui Banyan #F-206

    Maui Banyan #F-206

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $219 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  58. $203 to $276/night

    Nani Kai Hale # 502

    Nani Kai Hale # 502

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  59. $428 to $546/night

    Maui Kamaole #C-207

    Maui Kamaole #C-207

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $284 to $371/night

    Maui Kamaole #l-110

    Maui Kamaole #l-110

    1 BedroomBathroomsSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $258 to $393/night

    309

    309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $202 to $257/night

    Sealodge J2

    Sealodge J2

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  63. $350 to $417/night

    Kamaole Sands #04-406

    Kamaole Sands #04-406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $390 to $488/night

    Maui Banyan #G-201

    Maui Banyan #G-201

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $408 to $861/night

    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  67. $237/night

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults only

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults ...

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  68. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $235 to $317/night

    342

    342

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. $188 to $258/night

    133

    133

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  71. $134 to $213/night

    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    2 BedroomsBathroomsSleeps 4
    12 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $297 to $390/night

    Maui Kamaole #d-104

    Maui Kamaole #d-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $241 to $279/night

    Maui Vista #1302

    Maui Vista #1302

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  75. $298 to $350/night

    Maui Vista #1407

    Maui Vista #1407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  76. $344 to $460/night

    Kihei Surfside #107

    Kihei Surfside #107

    1 Bedroom BathroomSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  77. $177 to $225/night

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $393 to $480/night

    Kamaole Sands #10-405

    Kamaole Sands #10-405

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $290 to $332/night

    Kamaole Sands #06-106

    Kamaole Sands #06-106

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $152 to $443/night

    HOL 311

    HOL 311

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  81. $267 to $326/night

    Kauhale Makai #222

    Kauhale Makai #222

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $375 to $789/night

    Ilikai 1243

    Ilikai 1243

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $110 to $203/night

    Discovery Bay 1202

    Discovery Bay 1202

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  84. $486 to $554/night

    Maui Banyan #T-303

    Maui Banyan #T-303

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $258 to $340/night

    222

    222

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $188 to $258/night

    142

    142

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  87. $364 to $608/night

    Palm Villas F4 at Mauna Lani Resort

    Palm Villas F4 at Mauna Lani Resort

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  88. $181 to $242/night

    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  89. $241 to $301/night

    Cliffs 4202

    Cliffs 4202

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  91. $416 to $664/night

    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  92. $152 to $219/night

    Nani Kai Hale # 304

    Nani Kai Hale # 304

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  93. $113 to $135/night

    Kepuhi Beach 1192

    Kepuhi Beach 1192

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    FREE CANCELLATION
  94. $199 to $249/night

    WPH1801 2440 Kuhio Ave Honolulu THTC-CTOQ(XS)-01M-ACH

    WPH1801 2440 Kuhio Ave Honolulu THTC-CTOQ(XS)-01M-ACH

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $428 to $546/night

    Maui Kamaole #h-201

    Maui Kamaole #h-201

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $241 to $279/night

    Maui Vista #3111

    Maui Vista #3111

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  97. $305 to $390/night

    Kauhale Makai #512

    Kauhale Makai #512

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $202 to $636/night

    Aina Nalu Condo C208

    Aina Nalu Condo C208

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $249 to $302/night

    Unit 114

    Unit 114

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  100. $260/night

    Turtle Bay Takanoha**NUC 90-TVU-0557

    Turtle Bay Takanoha**NUC 90-TVU-0557

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION