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
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  2. CONDOMINIUM
    Hale Mahina #B403

    Hale Mahina #B403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $600/night

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

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  4. CONDOMINIUM
    Kaanapali Shores #159

    Kaanapali Shores #159

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $377 to $800/night

  5. CONDOMINIUM
    Maui Eldorado Condo K207

    Maui Eldorado Condo K207

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $207 to $501/night

  6. CONDOMINIUM
    Mahana Resort #906

    Mahana Resort #906

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $554/night

  7. CONDOMINIUM
    Hale Mahina #B101

    Hale Mahina #B101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $458/night

  8. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $429 to $800/night

  9. CONDOMINIUM
    Lahaina Shores #225

    Lahaina Shores #225

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $226 to $435/night

  10. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  11. CONDOMINIUM
    Papakea #A201

    Papakea #A201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $603/night

  12. CONDOMINIUM
    Maui Eldorado Condo A104

    Maui Eldorado Condo A104

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $262 to $565/night

  13. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  14. CONDOMINIUM
    Maui Kaanapali Villas #D275

    Maui Kaanapali Villas #D275

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $510/night

  15. CONDOMINIUM
    Kaanapali Royal #E302

    Kaanapali Royal #E302

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $566/night

  16. CONDOMINIUM
    Lahaina Shores #505

    Lahaina Shores #505

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $493/night

  17. CONDOMINIUM
    Pohailani #102

    Pohailani #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $145 to $249/night

  18. CONDOMINIUM
    Papakea #G103

    Papakea #G103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $600/night

  19. CONDOMINIUM
    Maui Kaanapali Villas #A517

    Maui Kaanapali Villas #A517

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $365/night

  20. HOUSE
    Mauna Kai 4

    Mauna Kai 4

    Princeville, HI

    Pool Hot Tub

    $235 to $283/night

  21. CONDOMINIUM
    Pali Ke Kua 107

    Pali Ke Kua 107

    Princeville, HI

    Pool

    $271 to $380/night

  22. CONDOMINIUM
    Maui Kaanapali Villas #A116

    Maui Kaanapali Villas #A116

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $365/night

  23. CONDOMINIUM
    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $377/night

  24. CONDOMINIUM
    Maui Eldorado Condo F201

    Maui Eldorado Condo F201

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $250 to $596/night

  25. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $934/night

  26. CONDOMINIUM
    Mahana Resort #1003

    Mahana Resort #1003

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $493/night

  27. CONDOMINIUM
    Maui Eldorado Condo G101

    Maui Eldorado Condo G101

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $169 to $408/night

  28. CONDOMINIUM
    Papakea #F105

    Papakea #F105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $226 to $491/night

  29. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  30. CONDOMINIUM
    Hale Mahina #A207

    Hale Mahina #A207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $414/night

  31. CONDOMINIUM
    Papakea #E207

    Papakea #E207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $447/night

  32. CONDOMINIUM
    Mahana Resort #813

    Mahana Resort #813

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $493/night

  33. CONDOMINIUM
    Mahana Resort #617

    Mahana Resort #617

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $638/night

  34. CONDOMINIUM
    Mahana Resort #1107

    Mahana Resort #1107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $638/night

  35. CONDOMINIUM
    Whaler #656

    Whaler #656

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $261 to $542/night

  36. CONDOMINIUM
    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $174 to $731/night

  37. CONDOMINIUM
    Poolside Aina Nalu Condo A101

    Poolside Aina Nalu Condo A101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $202 to $680/night

  38. CONDOMINIUM
    Poolside Aina Nalu Condo D101

    Poolside Aina Nalu Condo D101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $661/night

  39. CONDOMINIUM
    Lahaina Condo D106

    Lahaina Condo D106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $623/night

  40. CONDOMINIUM
    Aina Nalu Condo D110

    Aina Nalu Condo D110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  41. CONDOMINIUM
    Lahaina Condo I209

    Lahaina Condo I209

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  42. CONDOMINIUM
    Aina Nalu Condo I210

    Aina Nalu Condo I210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $604/night

  43. CONDOMINIUM
    Lahaina Condo J201

    Lahaina Condo J201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $680/night

  44. CONDOMINIUM
    Lahaina Condo J203

    Lahaina Condo J203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  45. CONDOMINIUM
    Lahaina Condo J204

    Lahaina Condo J204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  46. CONDOMINIUM
    Lahaina Condo J207

    Lahaina Condo J207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  47. CONDOMINIUM
    Lahaina Condo K109

    Lahaina Condo K109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  48. CONDOMINIUM
    Aina Nalu Premier Condo H207

    Aina Nalu Premier Condo H207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $192 to $579/night

  49. CONDOMINIUM
    Aina Nalu Premier Platinum C206

    Aina Nalu Premier Platinum C206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $584/night

  50. CONDOMINIUM
    Aina Nalu Condo I102

    Aina Nalu Condo I102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  51. CONDOMINIUM
    Aina Nalu Condo H208

    Aina Nalu Condo H208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $609/night

  52. CONDOMINIUM
    Aina Nalu Condo H104

    Aina Nalu Condo H104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $192 to $579/night

  53. CONDOMINIUM
    Noelani 211- Modern, Upscale Ocean Front Condo

    Noelani 211- Modern, Upscale Ocean Front Condo

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $371/night

  54. CONDOMINIUM
    Maui Eldorado Condo A210

    Maui Eldorado Condo A210

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $207 to $501/night

  55. CONDOMINIUM
    Maui Eldorado Condo G203

    Maui Eldorado Condo G203

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $187 to $433/night

  56. CONDOMINIUM
    Maui Eldorado Condo K212

    Maui Eldorado Condo K212

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $282 to $709/night

  57. CONDOMINIUM
    Maui Eldorado Condo J123

    Maui Eldorado Condo J123

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $282 to $628/night

  58. CONDOMINIUM
    Maui Eldorado Condo B104

    Maui Eldorado Condo B104

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $237 to $502/night

  59. CONDOMINIUM
    Maui Eldorado Condo J206

    Maui Eldorado Condo J206

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $282 to $628/night

  60. CONDOMINIUM
    Lahaina Shores #704

    Lahaina Shores #704

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $447/night

  61. CONDOMINIUM
    Mahana Resort #1217

    Mahana Resort #1217

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $354 to $606/night

  62. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  63. CONDOMINIUM
    Aina Nalu #I109

    Aina Nalu #I109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $580/night

  64. CONDOMINIUM
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $493 to $1,467/night

  65. CONDOMINIUM
    Lahaina Shores #532

    Lahaina Shores #532

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $162 to $360/night

  66. CONDOMINIUM
    Mahana Resort #612

    Mahana Resort #612

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $476/night

  67. CONDOMINIUM
    Kaanapali Royal #P101

    Kaanapali Royal #P101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $261 to $600/night

  68. CONDOMINIUM
    Mahana Resort #1205

    Mahana Resort #1205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $606/night

  69. HOUSE
    Pineapple Hale

    Pineapple Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $574 to $1,871/night

  70. CONDOMINIUM
    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $465 to $1,354/night

  71. TOWNHOUSE
    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $630/night

  72. CONDOMINIUM
    Fairway Villas M2 at the Waikoloa Beach Resort

    Fairway Villas M2 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $564/night

  73. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $299/night

  74. CONDOMINIUM
    Aina Nalu Condo A107

    Aina Nalu Condo A107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $190 to $664/night

  75. CONDOMINIUM
    Fairway Villas A-31

    Fairway Villas A-31

    WAIKOLOA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $244/night

  76. HOUSE
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Pool Hot Tub

    $506 to $2,069/night

  77. CONDOMINIUM
    Noelani 304 3bdrm 2.5 bath

    Noelani 304 3bdrm 2.5 bath

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $564 to $680/night

  78. CONDOMINIUM
    Maui Eldorado Condo B102

    Maui Eldorado Condo B102

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $237 to $502/night

  79. CONDOMINIUM
    Kaanapali Royal #P102

    Kaanapali Royal #P102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $261 to $601/night

  80. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,517/night

  81. CONDOMINIUM
    Papakea #C404

    Papakea #C404

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $412 to $940/night

  82. CONDOMINIUM
    Maui Kaanapali Villas #A221

    Maui Kaanapali Villas #A221

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $383/night

  83. CONDOMINIUM
    Maui Eldorado Condo J221

    Maui Eldorado Condo J221

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $220 to $501/night

  84. CONDOMINIUM
    Alii Kai 4103

    Alii Kai 4103

    Princeville, HI

    Pool

    $283 to $331/night

  85. CONDOMINIUM
    Hale Mahina #B102

    Hale Mahina #B102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $414/night

  86. CONDOMINIUM
    Maui Eldorado Condo K200

    Maui Eldorado Condo K200

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $345 to $816/night

  87. CONDOMINIUM
    Maui Eldorado Condo F101

    Maui Eldorado Condo F101

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $237 to $533/night

  88. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $229 to $365/night

  89. CONDOMINIUM
    Maui Eldorado Condo D108

    Maui Eldorado Condo D108

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $358 to $816/night

  90. CONDOMINIUM
    Mahana Resort #1103

    Mahana Resort #1103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $493/night

  91. CONDOMINIUM
    Lahaina Shores #522

    Lahaina Shores #522

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $157 to $360/night

  92. CONDOMINIUM
    Maui Kaanapali Villas #C160

    Maui Kaanapali Villas #C160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $197 to $354/night

  93. CONDOMINIUM
    Papakea #K303

    Papakea #K303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $619/night

  94. CONDOMINIUM
    Papakea #K203

    Papakea #K203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $283 to $600/night

  95. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  96. CONDOMINIUM
    Hale Mahina #A205

    Hale Mahina #A205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $414/night

  97. CONDOMINIUM
    Honua Kai-Konea #537

    Honua Kai-Konea #537

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $667/night

  98. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Pool Hot Tub

    $253 to $271/night

  99. CONDOMINIUM
    Lahaina Shores #321

    Lahaina Shores #321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $435/night

  100. CONDOMINIUM
    Mahana Resort #305

    Mahana Resort #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $307 to $606/night