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. $152 to $169/night

    Ke Nani Kai 113

    Ke Nani Kai 113

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  2. $152 to $197/night

    Ke Nani Kai 237

    Ke Nani Kai 237

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  3. $113 to $135/night

    Kepuhi Beach 1226

    Kepuhi Beach 1226

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $113 to $135/night

    Kepuhi Beach 1192

    Kepuhi Beach 1192

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    FREE CANCELLATION
  5. $113 to $135/night

    Kepuhi Beach 1234

    Kepuhi Beach 1234

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  6. $113 to $135/night

    Kepuhi Beach 1182

    Kepuhi Beach 1182

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  7. $225 to $281/night

    A Ala Hale

    A Ala Hale

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  8. $113 to $152/night

    Wavecrest B209

    Wavecrest B209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  9. $1,124 to $1,624/night

    Kaanapali Alii 456

    Kaanapali Alii 456

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $377 to $591/night

    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  11. $669 to $1,450/night

    Papakea B405

    Papakea B405

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $135 to $158/night

    Kepuhi Beach Resort 2222

    Kepuhi Beach Resort 2222

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  13. $225 to $338/night

    Hale Hiamoe

    Hale Hiamoe

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  14. $661 to $1,398/night

    Mahana 701

    Mahana 701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $220 to $238/night

    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $169 to $261/night

    Kahana Reef 303

    Kahana Reef 303

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $274 to $336/night

    Honokeana Cove 103

    Honokeana Cove 103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $185 to $316/night

    Kaleialoha 202

    Kaleialoha 202

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $274 to $440/night

    Kahana Sunset E4

    Kahana Sunset E4

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $402 to $524/night

    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  21. $218 to $676/night

    Mauna Lani Fairways #803

    Mauna Lani Fairways #803

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $194 to $648/night

    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $353 to $429/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $289 to $435/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $231 to $448/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. $324 to $531/night

    Kulakane 307

    Kulakane 307

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $219 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $311 to $736/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  32. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  33. $259 to $428/night

    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  34. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $416 to $664/night

    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  36. $180 to $345/night

    Kaanapali Shores 936

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $406 to $585/night

    Hale Ono Loa 409

    Hale Ono Loa 409

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $299 to $449/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $219 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $234 to $325/night

    Polynesian Shores 111

    Polynesian Shores 111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $336 to $505/night

    ROYAL MAUIAN, #607

    ROYAL MAUIAN, #607

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  44. $258 to $405/night

    KAMAOLE NALU, #104

    KAMAOLE NALU, #104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  45. $212 to $309/night

    KIHEI BEACH, #405

    KIHEI BEACH, #405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  46. $342 to $538/night

    KAMAOLE NALU, #605

    KAMAOLE NALU, #605

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  47. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  49. $212 to $309/night

    KIHEI BEACH, #404

    KIHEI BEACH, #404

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  50. $296 to $448/night

    KIHEI BEACH, #501

    KIHEI BEACH, #501

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  51. $174 to $339/night

    Kaleialoha 401

    Kaleialoha 401

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  53. $504 to $896/night

    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  54. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $293 to $356/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $897 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  57. $775 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  58. $183 to $454/night

    Hale Ono Loa 101

    Hale Ono Loa 101

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $212 to $309/night

    KIHEI BEACH, #406^

    KIHEI BEACH, #406^

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  60. $258 to $405/night

    KAMAOLE NALU, #503

    KAMAOLE NALU, #503

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  61. $185 to $377/night

    WAILEA EKAHI, #24B^

    WAILEA EKAHI, #24B^

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  62. $212 to $309/night

    KIHEI BEACH, #207

    KIHEI BEACH, #207

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  63. $313 to $504/night

    WAILEA ELUA, #2101*

    WAILEA ELUA, #2101*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  64. $212 to $309/night

    KIHEI BEACH, #407

    KIHEI BEACH, #407

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  65. $241 to $326/night

    KIHEI BEACH, #606

    KIHEI BEACH, #606

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  66. $302 to $438/night

    ROYAL MAUIAN, #219

    ROYAL MAUIAN, #219

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  67. $223 to $309/night

    KIHEI BEACH, #603^

    KIHEI BEACH, #603^

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
  68. $336 to $672/night

    WAILEA GRAND CHAMPION, #154

    WAILEA GRAND CHAMPION, #154

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  69. $167 to $427/night

    KIHEI SURFSIDE, #612

    KIHEI SURFSIDE, #612

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    Pool
  70. $897 to $1,459/night

    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  71. $202 to $343/night

    KAMAOLE NALU, #201

    KAMAOLE NALU, #201

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  72. $212 to $309/night

    KIHEI BEACH, #107

    KIHEI BEACH, #107

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  73. $336 to $392/night

    ROYAL MAUIAN, #208^

    ROYAL MAUIAN, #208^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  74. $291 to $605/night

    ROYAL MAUIAN, #315

    ROYAL MAUIAN, #315

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  75. $488 to $560/night

    MENEHUNE SHORES, #515

    MENEHUNE SHORES, #515

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  76. $167 to $448/night

    KIHEI SURFSIDE, #211

    KIHEI SURFSIDE, #211

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    Pool
  77. $336 to $505/night

    ROYAL MAUIAN, #516

    ROYAL MAUIAN, #516

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  78. $724 to $1,065/night

    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  79. $577 to $679/night

    MENEHUNE SHORES, #510**^

    MENEHUNE SHORES, #510**^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  80. $482 to $868/night

    WAILEA ELUA, #0302

    WAILEA ELUA, #0302

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  81. $223 to $309/night

    KIHEI BEACH, #307

    KIHEI BEACH, #307

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  82. $459 to $856/night

    WAILEA ELUA, #2003

    WAILEA ELUA, #2003

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  83. $724 to $1,065/night

    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  84. $191 to $332/night

    KAMAOLE NALU, #601

    KAMAOLE NALU, #601

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  85. $250 to $346/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $200 to $375/night

    Maui Sands Seaside 718

    Maui Sands Seaside 718

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  87. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  88. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  89. $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
  90. $263 to $421/night

    KIHEI BEACH, #409

    KIHEI BEACH, #409

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  91. $448 to $702/night

    ROYAL MAUIAN, #518^

    ROYAL MAUIAN, #518^

    3 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool
  92. $258 to $405/night

    KAMAOLE NALU, #602

    KAMAOLE NALU, #602

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  93. $393 to $560/night

    SUGAR BEACH RESORT, #PH12

    SUGAR BEACH RESORT, #PH12

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  94. $291 to $425/night

    WAILEA EKAHI, #33B

    WAILEA EKAHI, #33B

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  95. $202 to $387/night

    SUGAR BEACH RESORT, #518^

    SUGAR BEACH RESORT, #518^

    1 Bedroom BathroomSleeps 2
    7 nights minstay
    Pool Hot Tub
  96. $342 to $538/night

    KAMAOLE NALU, #105

    KAMAOLE NALU, #105

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  97. $448 to $897/night

    WAILEA ELUA, #2106

    WAILEA ELUA, #2106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  98. $482 to $1,009/night

    WAILEA ELUA, #0702

    WAILEA ELUA, #0702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  99. $167 to $427/night

    KIHEI SURFSIDE, #506

    KIHEI SURFSIDE, #506

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
  100. $236 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION