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. $309 to $366/night

    Kahana Sunset B6

    Kahana Sunset B6

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pool
  2. $443 to $1,022/night

    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  3. $501 to $1,093/night

    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  4. $408 to $1,383/night

    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  5. $397 to $1,093/night

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    2 BedroomsBathroomsSleeps 4
    6 nights minstay
    Pool Hot Tub
  6. $214 to $270/night

    Kahana Sunset C1C

    Kahana Sunset C1C

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  7. $428 to $484/night

    Kahana Sunset A4

    Kahana Sunset A4

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  8. $236 to $276/night

    Sands Of Kahana 318

    Sands Of Kahana 318

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  9. $506 to $563/night

    Sands Of Kahana 315

    Sands Of Kahana 315

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  10. $444 to $557/night

    Sands Of Kahana 275

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  11. $219 to $276/night

    Kahana Sunset C4

    Kahana Sunset C4

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  12. $276 to $332/night

    Kahana Sunset D9

    Kahana Sunset D9

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  13. $158 to $203/night

    Napili Bay 204

    Napili Bay 204

    Studio BathroomSleeps 4
    4 nights minstay
  14. $276 to $332/night

    Kahana Sunset D6

    Kahana Sunset D6

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  15. $141 to $208/night

    Nani Kai Hale # 507

    Nani Kai Hale # 507

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  16. $506 to $563/night

    Sands Of Kahana 215

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  17. $241 to $312/night

    Valley Isle 110

    Valley Isle 110

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $501 to $1,325/night

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  19. $256 to $436/night

    Kuleana 208 1 Bdrm

    Kuleana 208 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  20. $279 to $350/night

    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  21. $755 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $281 to $474/night

    Hale Kai 208 2bdrm 2bath

    Hale Kai 208 2bdrm 2bath

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  23. $251 to $384/night

    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  24. $513 to $977/night

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  25. $390 to $958/night

    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $656 to $875/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  27. $139 to $339/night

    Kuleana 321

    Kuleana 321

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $419 to $715/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $206 to $455/night

    Kaleialoha 205

    Kaleialoha 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $124 to $318/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $263 to $573/night

    Kaanapali Shores 725

    Kaanapali Shores 725

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $198 to $374/night

    Kahana Reef 201

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $161 to $359/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $289 to $666/night

    Mahana 1008

    Mahana 1008

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $211 to $379/night

    Hololani A204

    Hololani A204

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $210 to $400/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $236 to $564/night

    Kulakane 301

    Kulakane 301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $374 to $689/night

    Kaanapali Shores 515

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $150 to $324/night

    Valley Isle 902

    Valley Isle 902

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $131 to $289/night

    Kulakane 211

    Kulakane 211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $354 to $658/night

    Sands of Kahana 354

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $249 to $689/night

    Kaanapali Shores 613

    Kaanapali Shores 613

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $161 to $286/night

    Maalaea Banyans 203

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $234 to $556/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $251 to $490/night

    Island Sands 210

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $234 to $515/night

    Paki Maui 123

    Paki Maui 123

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $319 to $795/night

    Hale Ono Loa 109

    Hale Ono Loa 109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. $150 to $328/night

    Hale Ono Loa 214

    Hale Ono Loa 214

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  49. $152 to $443/night

    Kaleialoha #215

    Kaleialoha #215

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $501 to $619/night

    Sands of Kahana 366

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  51. $164 to $502/night

    Kaleialoha #313

    Kaleialoha #313

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $354 to $444/night

    Paki Maui 422

    Paki Maui 422

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  53. $210 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $282 to $477/night

    Honua Kai Konea 508

    Honua Kai Konea 508

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $506 to $563/night

    Sands Of Kahana 234

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  56. $276 to $332/night

    Kahana Sunset D7

    Kahana Sunset D7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  57. $311 to $365/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  60. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  61. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  62. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  63. $428 to $484/night

    Kahana Sunset A5

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  64. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  65. $276 to $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  66. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  67. $253 to $309/night

    Kahana Sunset B1

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  68. $306 to $358/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $152 to $219/night

    Nani Kai Hale 307

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. $152 to $219/night

    Nani Kai Hale # 405

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  71. $174 to $731/night

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  72. $276 to $332/night

    Kahana Sunset E8

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  73. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  74. $141 to $197/night

    Nani Kai Hale # 301

    Nani Kai Hale # 301

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  75. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  76. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $432 to $861/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  78. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  79. $571 to $1,789/night

    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  80. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  81. $207 to $257/night

    Wailua Bay View 204

    Wailua Bay View 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. $270 to $650/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $186 to $333/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $366 to $841/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $256 to $693/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $201 to $456/night

    Mahana 602

    Mahana 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $249 to $546/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $176 to $465/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $161 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $186 to $316/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $339 to $717/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  94. $397 to $1,209/night

    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  95. $243 to $292/night

    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  96. $443 to $861/night

    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  97. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  98. $508 to $1,789/night

    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  99. $181 to $329/night

    Hale Ono Loa 106

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $181 to $239/night

    Hale Pineapple

    Hale Pineapple

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION