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. $360 to $557/night

    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  2. $162 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  3. $282 to $528/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  4. $456 to $652/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  5. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  6. $208 to $347/night

    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  7. $208 to $347/night

    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  8. $340 to $503/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  9. $195 to $381/night

    Pikake A-4

    Pikake A-4

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    FREE CANCELLATION
  10. $267 to $418/night

    Luana Kai #A-103

    Luana Kai #A-103

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $238 to $275/night

    Sealodge J1

    Sealodge J1

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  12. $177 to $357/night

    Luana Kai #C-203

    Luana Kai #C-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  13. $227 to $340/night

    Maui Sunset #A-117

    Maui Sunset #A-117

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $139 to $244/night

    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  15. $218 to $389/night

    Maui Sunset #A-509

    Maui Sunset #A-509

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  17. $393 to $544/night

    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $208 to $347/night

    Menehune Shores #425

    Menehune Shores #425

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  19. $206 to $363/night

    Maui Sunset #A-407

    Maui Sunset #A-407

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  21. $334 to $556/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  22. $208 to $296/night

    Koa Lagoon #505

    Koa Lagoon #505

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  23. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  24. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  25. $201 to $409/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  26. $304 to $467/night

    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    FREE CANCELLATION
  27. $238 to $275/night

    Sealodge D1

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. $397 to $977/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  29. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. $278 to $495/night

    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  31. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  32. $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
  33. $1,413 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  34. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $226 to $238/night

    Sealodge F9

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  36. $161 to $266/night

    Kauhale Makai #330

    Kauhale Makai #330

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $157 to $277/night

    Waiohuli Beach Hale #B-206

    Waiohuli Beach Hale #B-206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. $218 to $409/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  39. $137 to $470/night

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. $456 to $572/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  41. $350 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
  42. $228 to $437/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $296 to $521/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  45. $238 to $291/night

    Sealodge G8

    Sealodge G8

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $274 to $521/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  47. $218 to $383/night

    Leinaala Oceanfront #104

    Leinaala Oceanfront #104

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $157 to $277/night

    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  49. $216 to $389/night

    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  50. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  51. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  52. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  53. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  54. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  55. $372 to $524/night

    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. $416 to $664/night

    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  57. $208 to $347/night

    Menehune Shores #401

    Menehune Shores #401

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  58. $556 to $927/night

    Hale Ili Ili #D

    Hale Ili Ili #D

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $226 to $257/night

    Sealodge J2

    Sealodge J2

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. $311 to $429/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  61. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  62. $145 to $569/night

    Lahaina Shores 210

    Lahaina Shores 210

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  63. $236 to $636/night

    Kuleana 313

    Kuleana 313

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  64. $322 to $426/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  65. $238 to $275/night

    Sealodge E10

    Sealodge E10

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  66. $759 to $1,395/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $206 to $367/night

    Waiohuli Beach Hale #D-223

    Waiohuli Beach Hale #D-223

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. $695 to $1,043/night

    Hale Ili Ili #A

    Hale Ili Ili #A

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $208 to $255/night

    Waiohuli Beach Hale #A-203

    Waiohuli Beach Hale #A-203

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. $226 to $257/night

    Sealodge G4

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  71. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $157 to $277/night

    Waiohuli Beach Hale #B-205

    Waiohuli Beach Hale #B-205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $358 to $1,095/night

    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $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
  75. $428 to $579/night

    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $238 to $275/night

    Sealodge C7

    Sealodge C7

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  77. $173 to $381/night

    Noelani #219

    Noelani #219

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $232 to $406/night

    Waiohuli Beach Hale #C-111

    Waiohuli Beach Hale #C-111

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  79. $259 to $428/night

    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  80. $416 to $664/night

    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  81. $304 to $467/night

    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  82. $416 to $664/night

    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  83. $304 to $467/night

    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  84. $240 to $437/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  85. $218 to $389/night

    Waiohuli Beach Hale #D-225

    Waiohuli Beach Hale #D-225

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $608 to $790/night

    Hale Huna Kai- Oceanfront

    Hale Huna Kai- Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  87. $218 to $330/night

    Hoyochi Nikko #202

    Hoyochi Nikko #202

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  88. $275 to $306/night

    Alii Kai 5301

    Alii Kai 5301

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  89. $259 to $428/night

    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  90. $157 to $277/night

    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  91. $208 to $347/night

    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION