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. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

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

    Kahana Sunset D2

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  3. $158 to $191/night

     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

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

    Kahana Sunset C7

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  5. $369 to $594/night

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  6. $428 to $484/night

    Kahana Sunset F4

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  7. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  8. $582 to $1,325/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  9. $236 to $304/night

    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  10. $371 to $484/night

    Kahana Sunset F6

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  11. $193 to $359/night

    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $456 to $634/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  13. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  14. $274 to $409/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  15. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  16. $478 to $1,673/night

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  17. $162 to $452/night

    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $226 to $430/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $211 to $389/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $136 to $249/night

    Royal Kahana 618

    Royal Kahana 618

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $291 to $588/night

    Hale Ono Loa 409

    Hale Ono Loa 409

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. $336 to $746/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $199 to $388/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $513 to $1,789/night

    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  25. $362 to $977/night

    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  26. $397 to $1,209/night

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  27. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $194 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $186 to $214/night

    Kahana Sunset B3B

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  30. $436 to $572/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  31. $428 to $484/night

    Kahana Sunset F2

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  32. $740 to $2,021/night

    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  33. $326 to $350/night

    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $226 to $453/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $208 to $253/night

    Sands Of Kahana 231

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  36. $215 to $430/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $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
  38. $311 to $457/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  39. $276 to $332/night

    Kahana Sunset D8

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  40. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $186 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $253 to $366/night

    Kahana Sunset B3

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  43. $204 to $235/night

    Lil Grass Shack-103

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  44. $210 to $430/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $218 to $274/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  46. $1,392 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  47. $124 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $253 to $309/night

    Kahana Sunset D10

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  49. $309 to $366/night

    Kahana Sunset B7

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  50. $362 to $977/night

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  51. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  52. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  53. $276 to $332/night

    Kahana Sunset E8

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  54. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  55. $253 to $309/night

    Kahana Sunset B1

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  56. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  57. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  58. $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
  59. $167 to $296/night

    Kaleialoha 112

    Kaleialoha 112

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  60. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  61. $227 to $257/night

    Wailua Bay View 204

    Wailua Bay View 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $455 to $1,035/night

    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  63. $432 to $1,499/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  64. $311 to $564/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  65. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  66. $262 to $547/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  67. $201 to $274/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  68. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  69. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  71. $234 to $683/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $216 to $364/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $224 to $516/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $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
  75. $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
  76. $397 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
  77. $193 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  79. $246 to $509/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $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
  81. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  82. $149 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $275 to $413/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  85. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  86. $219 to $596/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $150 to $333/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $188 to $258/night

    107

    107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  89. $186 to $334/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  91. $428 to $484/night

    Kahana Sunset A5

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  92. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  93. $158 to $191/night

    Ka Hale Kaeloha (House of Love) – Romantic Oceanside Condo

    Ka Hale Kaeloha (House of Love) – Romantic Oceanside C...

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  94. $145 to $569/night

    Lahaina Shores 210

    Lahaina Shores 210

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  95. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $236 to $636/night

    Kuleana 313

    Kuleana 313

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  97. $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
  98. $276 to $332/night

    Kahana Sunset D9

    Kahana Sunset D9

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  99. $304 to $467/night

    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  100. $506 to $563/night

    Sands Of Kahana 215

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub