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
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  2. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  3. CONDOMINIUM
    Papakea E306

    Papakea E306

    Lahaina, HI

    Pool Hot Tub

    $183 to $314/night

  4. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  5. CONDOMINIUM
    Kihei Bay Surf #213

    Kihei Bay Surf #213

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  6. CONDOMINIUM
    Kihei Bay Vista #A-201

    Kihei Bay Vista #A-201

    Kihei, HI

    Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  7. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  8. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  9. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  10. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  11. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  12. CONDOMINIUM
    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  13. CONDOMINIUM
    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  14. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $467/night

  15. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  16. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $422/night

  17. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $227 to $339/night

  18. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $247 to $420/night

  19. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $398/night

  20. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $420/night

  21. CONDOMINIUM
    Palms at Wailea #604

    Palms at Wailea #604

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $451/night

  22. CONDOMINIUM
    Maui Kamaole #J-217

    Maui Kamaole #J-217

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $371/night

  23. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  24. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  25. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $614/night

  26. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  27. CONDOMINIUM
    Kihei Bay Surf #123

    Kihei Bay Surf #123

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  28. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $488/night

  29. CONDOMINIUM
    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  30. CONDOMINIUM
    Kihei Bay Vista #D-208

    Kihei Bay Vista #D-208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $219/night

  31. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  32. CONDOMINIUM
    Pacific Shores #A-101

    Pacific Shores #A-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $158 to $244/night

  33. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  34. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  35. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $266/night

  36. CONDOMINIUM
    Shores of Maui #211

    Shores of Maui #211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $335/night

  37. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  38. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  39. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $347/night

  40. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $209/night

  41. CONDOMINIUM
    Maui Kamaole #F-210

    Maui Kamaole #F-210

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $360/night

  42. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  43. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  44. CONDOMINIUM
    Kihei Bay Surf #253

    Kihei Bay Surf #253

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  45. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $465/night

  46. CONDOMINIUM
    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $409/night

  47. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $413/night

  48. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $464/night

  49. CONDOMINIUM
    Maui Sunset #B-106

    Maui Sunset #B-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $303/night

  50. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $354/night

  51. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $416 to $708/night

  52. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $662/night

  53. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $739 to $1,723/night

  54. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $418/night

  55. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  56. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  57. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  58. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  59. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  60. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  61. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  62. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  63. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $551 to $922/night

  64. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  65. CONDOMINIUM
    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $244/night

  66. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $183/night

  67. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $273/night

  68. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $458/night

  69. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  70. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Pool Hot Tub

    $162 to $401/night

  71. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  72. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $429/night

  73. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  74. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $346/night

  75. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $360/night

  76. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  77. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  78. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $521/night

  79. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  80. CONDOMINIUM
    Kihei Garden Estates #A-102

    Kihei Garden Estates #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $196/night

  81. CONDOMINIUM
    Kona Makai 3-203

    Kona Makai 3-203

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $239/night

  82. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $348/night

  83. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $282 to $477/night

  84. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $303 to $515/night

  85. CONDOMINIUM
    Kamaole Sands #1-406

    Kamaole Sands #1-406

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $454/night

  86. CONDOMINIUM
    Grand Champions #151

    Grand Champions #151

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $398/night

  87. CONDOMINIUM
    Palms at Wailea #702

    Palms at Wailea #702

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $281 to $473/night

  88. CONDOMINIUM
    Palms at Wailea #1005

    Palms at Wailea #1005

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $325 to $552/night

  89. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  90. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night