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. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  2. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  3. CONDOMINIUM
    MAKENA SURF RESORT, #G-304

    MAKENA SURF RESORT, #G-304

    Makena, Maui, HI

    Pool Hot Tub

    $1,066 to $1,459/night

  4. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  5. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  6. CONDOMINIUM
    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    Wailea, Maui, HI

    Pool Hot Tub

    $931 to $1,459/night

  7. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,564/night

  8. CONDOMINIUM
    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    Wailea, Maui, HI

    Pool Hot Tub

    $841 to $1,515/night

  9. CONDOMINIUM
    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    Wailea, Maui,, HI

    Pool Hot Tub

    $785 to $1,347/night

  10. CONDOMINIUM
    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua, HI

    $781 to $1,219/night

  11. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $781 to $1,219/night

  12. CONDOMINIUM
    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  13. CONDOMINIUM
    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  14. CONDOMINIUM
    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  15. CONDOMINIUM
    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    Makena, Maui, HI

    Pool Hot Tub

    $762 to $1,094/night

  16. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  17. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  18. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

  19. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  20. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  21. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  22. CONDOMINIUM
    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua, HI

    Pool

    $594 to $969/night

  23. CONDOMINIUM
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    Pool

    $594 to $1,063/night

  24. CONDOMINIUM
    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    Makena, Maui, HI

    Pool Hot Tub

    $583 to $926/night

  25. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  26. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  27. CONDOMINIUM
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  28. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  29. CONDOMINIUM
    MAKENA SURF RESORT, #F-209

    MAKENA SURF RESORT, #F-209

    Makena, Maui, HI

    Pool Hot Tub

    $560 to $1,094/night

  30. CONDOMINIUM
    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    Makena, Maui, HI

    Pool Hot Tub

    $549 to $926/night

  31. CONDOMINIUM
    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    Makena, Maui, HI

    Pool Hot Tub

    $549 to $926/night

  32. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  33. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  34. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,789/night

  35. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  36. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  37. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  38. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  39. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  40. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  41. CONDOMINIUM
    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua, HI

    Pool

    $494 to $781/night

  42. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  43. CONDOMINIUM
    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    Wailea, Maui, HI

    Pool Hot Tub

    $471 to $896/night

  44. CONDOMINIUM
    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    Wailea, Maui, HI

    Pool Hot Tub

    $471 to $896/night

  45. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469 to $735/night

  46. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  47. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  48. CONDOMINIUM
    Sands Of Kahana 275

    Sands Of Kahana 275

    Lahaina, HI

    Pool Hot Tub

    $444 to $557/night

  49. CONDOMINIUM
    MAKENA SURF RESORT, #A-101

    MAKENA SURF RESORT, #A-101

    Makena, Maui, HI

    Pool Hot Tub

    $437 to $785/night

  50. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $429 to $800/night

  51. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  52. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  53. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  54. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  55. CONDOMINIUM
    Mahana 519

    Mahana 519

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $410 to $850/night

  56. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    Kapolei, HI

    Pool Hot Tub

    $408 to $977/night

  57. CONDOMINIUM
    Ilikai #1743

    Ilikai #1743

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $404 to $619/night

  58. CONDOMINIUM
    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $384 to $783/night

  59. CONDOMINIUM
    C1-2 Bedroom Oceanfront

    C1-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  60. CONDOMINIUM
    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  61. CONDOMINIUM
    Kaanapali Shores #159

    Kaanapali Shores #159

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $377 to $800/night

  62. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $770/night

  63. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  64. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $989/night

  65. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  66. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $361 to $749/night

  67. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  68. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $965/night

  69. CONDOMINIUM
    Paki Maui 422

    Paki Maui 422

    Lahaina, HI

    Pool Hot Tub

    $354 to $444/night

  70. CONDOMINIUM
    Royal Kahana #911

    Royal Kahana #911

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $354 to $963/night

  71. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  72. CONDOMINIUM
    Mauna Lani Terrace K301

    Mauna Lani Terrace K301

    Kamuela, HI

    Pool
    FREE CANCELLATION

    $340 to $644/night

  73. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $340 to $1,060/night

  74. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $338 to $948/night

  75. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  76. CONDOMINIUM
    Royal Kahana #1211

    Royal Kahana #1211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $969/night

  77. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $1,016/night

  78. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  79. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  80. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  81. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $350/night

  82. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $314 to $649/night

  83. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $594/night

  84. CONDOMINIUM
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $309 to $925/night

  85. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $308 to $1,016/night

  86. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  87. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  88. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  89. CONDOMINIUM
    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  90. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  91. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  92. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $475/night

  93. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  94. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $289 to $502/night

  95. CONDOMINIUM
    Kulakane 306

    Kulakane 306

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  96. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $625/night

  97. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  98. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  99. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  100. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night