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. $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
  2. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  3. $350 to $977/night

    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  4. $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
  5. $202 to $387/night

    SUGAR BEACH RESORT, #329

    SUGAR BEACH RESORT, #329

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
  6. $208 to $253/night

    Sands Of Kahana 231

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  7. $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
  8. $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
  9. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  10. $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
  11. $236 to $304/night

    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  12. $397 to $551/night

    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $193 to $359/night

    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $311 to $457/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  15. $436 to $572/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  16. $456 to $634/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  17. $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
  18. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $448 to $897/night

    WAILEA ELUA, #2106

    WAILEA ELUA, #2106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  20. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $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
  23. $194 to $669/night

    KAUHALE MAKAI #532

    KAUHALE MAKAI #532

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $233 to $453/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $234 to $483/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $194 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $210 to $430/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $202 to $387/night

    SUGAR BEACH RESORT, #518^

    SUGAR BEACH RESORT, #518^

    1 Bedroom BathroomSleeps 2
    7 nights minstay
    Pool Hot Tub
  29. $504 to $896/night

    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  30. $897 to $1,459/night

    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  31. $482 to $1,009/night

    WAILEA ELUA, #0702

    WAILEA ELUA, #0702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  32. $459 to $856/night

    WAILEA ELUA, #2003

    WAILEA ELUA, #2003

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  33. $785 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  34. $313 to $504/night

    WAILEA ELUA, #2101*

    WAILEA ELUA, #2101*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  35. $286 to $560/night

    SUGAR BEACH RESORT, #PH12

    SUGAR BEACH RESORT, #PH12

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  36. $762 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  37. $482 to $868/night

    WAILEA ELUA, #0302

    WAILEA ELUA, #0302

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  38. $724 to $1,065/night

    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  39. $724 to $1,065/night

    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  40. $202 to $387/night

    SUGAR BEACH RESORT, #414^

    SUGAR BEACH RESORT, #414^

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

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $226 to $430/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $211 to $389/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $188 to $348/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $211 to $400/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $215 to $430/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $336 to $746/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $124 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $199 to $388/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $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
  51. $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
  52. $470 to $953/night

    WAILEA ELUA, #2010

    WAILEA ELUA, #2010

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  53. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  54. $470 to $953/night

    WAILEA ELUA, #0801*

    WAILEA ELUA, #0801*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  55. $634 to $896/night

    WAILEA ELUA, #1309

    WAILEA ELUA, #1309

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  56. $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
  57. $855 to $1,319/night

    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  58. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  59. $362 to $422/night

    Pali Ke Kua 203

    Pali Ke Kua 203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  61. $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
  62. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  63. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  64. $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
  65. $275 to $413/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $253 to $301/night

    Cliffs 8205

    Cliffs 8205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $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
  68. $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
  69. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  70. $311 to $564/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  71. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  72. $513 to $966/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $627 to $1,065/night

    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  76. $262 to $547/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  77. $1,514 to $2,750/night

    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
  78. $329 to $528/night

    WAILEA ELUA, #0807

    WAILEA ELUA, #0807

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
  79. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  80. $246 to $509/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $149 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $538 to $1,065/night

    WAILEA ELUA, #0202*

    WAILEA ELUA, #0202*

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  83. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  84. $190 to $387/night

    SUGAR BEACH RESORT, #136^

    SUGAR BEACH RESORT, #136^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  85. $190 to $387/night

    SUGAR BEACH RESORT, #430^

    SUGAR BEACH RESORT, #430^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  86. $448 to $1,065/night

    WAILEA ELUA, #0902

    WAILEA ELUA, #0902

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  87. $202 to $387/night

    SUGAR BEACH RESORT, #PH23

    SUGAR BEACH RESORT, #PH23

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  88. $190 to $387/night

    SUGAR BEACH RESORT, #531

    SUGAR BEACH RESORT, #531

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  89. $190 to $387/night

    SUGAR BEACH RESORT, #524^

    SUGAR BEACH RESORT, #524^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  90. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  91. $437 to $953/night

    WAILEA ELUA, #0802

    WAILEA ELUA, #0802

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  92. $470 to $953/night

    WAILEA ELUA, #0105

    WAILEA ELUA, #0105

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  93. $202 to $387/night

    SUGAR BEACH RESORT, #418

    SUGAR BEACH RESORT, #418

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  94. $299 to $488/night

    WAILEA ELUA, #0106

    WAILEA ELUA, #0106

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
  95. $504 to $896/night

    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  96. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  98. $234 to $683/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $150 to $333/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $456 to $883/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION