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
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  2. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

  3. COTTAGE
    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $134 to $454/night

  4. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  5. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $448/night

  6. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  7. CONDOMINIUM
    Aina Nalu A104

    Aina Nalu A104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $228 to $499/night

  8. CONDOMINIUM
    Aina Nalu B204

    Aina Nalu B204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $243 to $577/night

  9. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  10. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $220 to $476/night

  11. CONDOMINIUM
    Aina Nalu C204

    Aina Nalu C204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $243 to $577/night

  12. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $213 to $446/night

  13. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $498/night

  14. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  15. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  16. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  17. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $366 to $501/night

  18. CONDOMINIUM
    Bay Villa 38G2

    Bay Villa 38G2

    Lahaina, HI

    Pool

    $248 to $304/night

  19. CONDOMINIUM
    Bay Villa 38G3

    Bay Villa 38G3

    Lahaina, HI

    Pool

    $248 to $304/night

  20. CONDOMINIUM
    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $242 to $309/night

  21. CONDOMINIUM
    Eldorado J109

    Eldorado J109

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $299/night

  22. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  23. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $613/night

  24. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $640/night

  25. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  26. CONDOMINIUM
    Golf Villa 19T4

    Golf Villa 19T4

    Lahaina, HI

    Pool

    $197 to $248/night

  27. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

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

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  29. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,384/night

  30. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

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

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $455 to $1,500/night

  32. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,500/night

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

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $559 to $1,784/night

  34. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

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

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,784/night

  36. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $185 to $275/night

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

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,016/night

  38. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,384/night

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

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

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

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,384/night

  41. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

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

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

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

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $490 to $1,668/night

  44. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $330/night

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

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

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

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  47. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,268/night

  48. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  49. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Pool Hot Tub

    $286 to $478/night

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

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  51. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $290/night

  52. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $314/night

  53. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $971/night

  54. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $953/night

  55. CONDOMINIUM
    Hale Ono Loa 416

    Hale Ono Loa 416

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $144 to $324/night

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

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $548 to $2,016/night

  57. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    FREE CANCELLATION

    $181 to $239/night

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

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,668/night

  59. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $264/night

  60. CONDOMINIUM
    HOL #216

    HOL #216

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $159 to $348/night

  61. CONDOMINIUM
    HOL 311

    HOL 311

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $348/night

  62. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  63. CONDOMINIUM
    Hololani A204

    Hololani A204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $425/night

  64. CONDOMINIUM
    Hololani A303

    Hololani A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $556/night

  65. CONDOMINIUM
    Honua Kai 1024

    Honua Kai 1024

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $429/night

  66. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $353/night

  67. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $370/night

  68. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  69. CONDOMINIUM
    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $328 to $487/night

  70. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  71. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  72. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  73. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $508 to $988/night

  74. CONDOMINIUM
    Honua Kai- Hokulani 108- Ground Floor & Huge Play Lawn! 1b/1b

    Honua Kai- Hokulani 108- Ground Floor & Huge Play La...

    Kaanapali, HI

    Pool Hot Tub

    $256 to $910/night

  75. CONDOMINIUM
    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View! 1b/1b

    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View!...

    Kaanapali, HI

    Pool Hot Tub

    $243 to $910/night

  76. CONDOMINIUM
    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Lahaina, HI

    Pool Hot Tub

    $389 to $1,446/night

  77. CONDOMINIUM
    Honua kai- Konea 301 Frontline with BBQ!

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $566 to $2,227/night

  78. CONDOMINIUM
    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b/1b

    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b...

    Kaanapali, HI

    Pool Hot Tub

    $257 to $894/night

  79. CONDOMINIUM
    Honua Kai- Konea 606- Partial Ocean and Mountain Views! 2b/1b

    Honua Kai- Konea 606- Partial Ocean and Mountain Views! ...

    Kaanapali, HI

    Pool Hot Tub

    $316 to $1,112/night

  80. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $825 to $2,810/night

  81. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  82. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $208 to $469/night

  83. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $185 to $444/night

  84. CONDOMINIUM
    Kaanapali Plantation #59

    Kaanapali Plantation #59

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $375/night

  85. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $625/night

  86. CONDOMINIUM
    Kaanapali Royal G102

    Kaanapali Royal G102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $521/night

  87. CONDOMINIUM
    Kaanapali Royal H303

    Kaanapali Royal H303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $625/night

  88. CONDOMINIUM
    Kaanapali Royal J202

    Kaanapali Royal J202

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $335 to $1,014/night

  89. CONDOMINIUM
    Kaanapali Royal Q101

    Kaanapali Royal Q101

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $346 to $964/night

  90. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $384 to $989/night

  91. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,018/night

  92. CONDOMINIUM
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $958/night

  93. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $378 to $1,018/night

  94. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $331/night

  95. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $435/night

  96. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $498/night

  97. CONDOMINIUM
    Kahana Manor 410

    Kahana Manor 410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $326/night

  98. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $136 to $401/night

  99. CONDOMINIUM
    Kahana Reef 111

    Kahana Reef 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $399/night

  100. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $355/night