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. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    FREE CANCELLATION

    $360 to $557/night

  2. CONDOMINIUM
    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Honolulu, HI

    FREE CANCELLATION

    $174 to $731/night

  3. CONDOMINIUM
    Royal Kahana 802

    Royal Kahana 802

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $162 to $569/night

  4. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool Hot Tub

    $456 to $659/night

  5. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool Hot Tub

    $299 to $452/night

  6. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  7. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $361 to $749/night

  8. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $432 to $1,499/night

  9. CONDOMINIUM
    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    Kihei, HI

    Pool
    FREE CANCELLATION

    $139 to $244/night

  10. CONDOMINIUM
    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    Kapaa, HI

    Pool Hot Tub

    $282 to $535/night

  11. CONDOMINIUM
    Royal Kahana 702

    Royal Kahana 702

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $333/night

  12. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  13. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $177 to $357/night

  14. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  15. CONDOMINIUM
    Sealodge J1

    Sealodge J1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  16. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $227 to $340/night

  17. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  18. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $264/night

  19. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $238 to $257/night

  20. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $218 to $389/night

  21. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  22. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  23. 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

  24. CONDOMINIUM
    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $633/night

  25. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  26. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $363/night

  27. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  28. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  29. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $571 to $1,789/night

  30. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $296/night

  31. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $239 to $348/night

  32. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $204 to $292/night

  33. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $409/night

  34. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    FREE CANCELLATION

    $304 to $467/night

  35. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,209/night

  36. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,789/night

  37. CONDOMINIUM
    Menehune Shores #425

    Menehune Shores #425

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  38. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  39. CONDOMINIUM
    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  40. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $397 to $977/night

  41. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  42. CONDOMINIUM
    Royal Kahana 318

    Royal Kahana 318

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $359/night

  43. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $278 to $495/night

  44. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  45. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  46. CONDOMINIUM
    107

    107

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  47. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  48. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  49. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  50. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    FREE CANCELLATION

    $163 to $239/night

  51. CONDOMINIUM
    Mahana 1113

    Mahana 1113

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $1,066/night

  52. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  53. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $284/night

  54. CONDOMINIUM
    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    Kapaa, HI

    Pool Hot Tub

    $334 to $556/night

  55. CONDOMINIUM
    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    Kapaa, HI

    Pool Hot Tub

    $340 to $503/night

  56. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  57. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $158 to $191/night

  58. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  59. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  60. CONDOMINIUM
    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $364/night

  61. CONDOMINIUM
    Waiohuli Beach Hale #B-206

    Waiohuli Beach Hale #B-206

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  62. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $264/night

  63. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $409/night

  64. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $176 to $606/night

  65. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

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

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  67. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  68. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  69. CONDOMINIUM
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $154 to $579/night

  70. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $572/night

  71. 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

  72. CONDOMINIUM
    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    Kihei, HI

    Pool
    FREE CANCELLATION

    $216 to $389/night

  73. CONDOMINIUM
    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  74. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  75. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $573 to $1,344/night

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

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

    Kihei, HI

    Pool
    FREE CANCELLATION

    $137 to $470/night

  77. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

  78. CONDOMINIUM
    Noelani # 115

    Noelani # 115

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $437/night

  79. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  80. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  81. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $291/night

  82. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  83. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,325/night

  84. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $155 to $531/night

  85. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $419 to $740/night

  86. CONDOMINIUM
    Nohonani #202

    Nohonani #202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  87. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  88. CONDOMINIUM
    Leinaala Oceanfront #104

    Leinaala Oceanfront #104

    Kihei, HI

    Pool
    FREE CANCELLATION

    $218 to $383/night

  89. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  90. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  91. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

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

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $302 to $326/night

  93. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $311 to $965/night

  94. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  95. CONDOMINIUM
    Menehune Shores #401

    Menehune Shores #401

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  96. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  97. COTTAGE
    Moloa'a Bay Cottage

    Moloa'a Bay Cottage

    Anahola, HI

    $430 to $515/night

  98. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $607/night

  99. CONDOMINIUM
    Lahaina Roads 309

    Lahaina Roads 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $213 to $438/night

  100. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,938 to $4,750/night