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. VILLA
    Kahana Villa E614

    Kahana Villa E614

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $248 to $641/night

  2. CONDOMINIUM
    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $247 to $649/night

  3. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    Wailea, HI

    Pool
    FREE CANCELLATION

    $302 to $724/night

  4. CONDOMINIUM
    Kihei Alii Kai #A-305

    Kihei Alii Kai #A-305

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $208/night

  5. CONDOMINIUM
    Waiohuli Beach Hale #A-203

    Waiohuli Beach Hale #A-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $255/night

  6. CONDOMINIUM
    Waiohuli Beach Hale #B-205

    Waiohuli Beach Hale #B-205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $277/night

  7. CONDOMINIUM
    Leinaala Oceanfront #105

    Leinaala Oceanfront #105

    Kihei, HI

    Pool
    FREE CANCELLATION

    $232 to $550/night

  8. CONDOMINIUM
    Maalaea Surf Resort #C-3

    Maalaea Surf Resort #C-3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $418/night

  9. CONDOMINIUM
    Grand Champions #86

    Grand Champions #86

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $325/night

  10. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  11. CONDOMINIUM
    Kamaole Sands #2-301

    Kamaole Sands #2-301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $282 to $645/night

  12. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  13. CONDOMINIUM
    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244/night

  14. CONDOMINIUM
    Kamaole Sands #3-307

    Kamaole Sands #3-307

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $441/night

  15. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $251 to $595/night

  16. CONDOMINIUM
    Kihei Bay Vista #C-106

    Kihei Bay Vista #C-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  17. CONDOMINIUM
    Maui Kamaole #L-205

    Maui Kamaole #L-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $254 to $602/night

  18. CONDOMINIUM
    Palms at Wailea #704

    Palms at Wailea #704

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $292 to $704/night

  19. CONDOMINIUM
    Kamaole Sands #4-201

    Kamaole Sands #4-201

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $406/night

  20. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  21. CONDOMINIUM
    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    Kihei, HI

    Pool
    FREE CANCELLATION

    $347/night

  22. CONDOMINIUM
    Puamana 9C

    Puamana 9C

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  23. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $447/night

  24. CONDOMINIUM
    Palms at Wailea #1209

    Palms at Wailea #1209

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $365/night

  25. CONDOMINIUM
    Kihei Bay Vista #A-102

    Kihei Bay Vista #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  26. CONDOMINIUM
    Kihei Bay Vista #D-202

    Kihei Bay Vista #D-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  27. CONDOMINIUM
    Wailea Ekolu #501

    Wailea Ekolu #501

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $521/night

  28. CONDOMINIUM
    Kihei Alii Kai #C-306

    Kihei Alii Kai #C-306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $133 to $226/night

  29. CONDOMINIUM
    Pali Ke Kua #241

    Pali Ke Kua #241

    Princeville, HI

    Pool

    $241 to $276/night

  30. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  31. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $467/night

  32. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $635/night

  33. CONDOMINIUM
    Grand Champions #45

    Grand Champions #45

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $556/night

  34. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $476/night

  35. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $212 to $502/night

  36. CONDOMINIUM
    Maui Vista #2-423

    Maui Vista #2-423

    Kihei, HI

    Pool
    FREE CANCELLATION

    $347/night

  37. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $347/night

  38. CONDOMINIUM
    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach

    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach...

    Kihei, HI

    Pool
    FREE CANCELLATION

    $112 to $353/night

  39. CONDOMINIUM
    Kihei Bay Surf #109

    Kihei Bay Surf #109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  40. CONDOMINIUM
    Haleakala Shores #A-212

    Haleakala Shores #A-212

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $331/night

  41. CONDOMINIUM
    Wailea Ekolu #503

    Wailea Ekolu #503

    Wailea, HI

    Pool
    FREE CANCELLATION

    $232 to $521/night

  42. CONDOMINIUM
    Maui Kamaole #J-103

    Maui Kamaole #J-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $342/night

  43. CONDOMINIUM
    Maui Kamaole #A-201

    Maui Kamaole #A-201

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $292 to $693/night

  44. CONDOMINIUM
    Papakea E306

    Papakea E306

    Lahaina, HI

    Pool Hot Tub

    $183 to $314/night

  45. CONDOMINIUM
    Leinaala Oceanfront #302

    Leinaala Oceanfront #302

    Kihei, HI

    Pool
    FREE CANCELLATION

    $161 to $278/night

  46. CONDOMINIUM
    Maui Vista #2-320

    Maui Vista #2-320

    Kihei, HI

    Pool
    FREE CANCELLATION

    $289/night

  47. CONDOMINIUM
    Kihei Akahi #DG06

    Kihei Akahi #DG06

    Kihei, HI

    Pool
    FREE CANCELLATION

    $126 to $231/night

  48. CONDOMINIUM
    Kamaole Sands #8-208

    Kamaole Sands #8-208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289/night

  49. CONDOMINIUM
    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  50. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  51. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  52. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    Pool
    FREE CANCELLATION

    $296/night

  53. CONDOMINIUM
    Kamaole Sands #9-203

    Kamaole Sands #9-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $208/night

  54. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  55. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  56. CONDOMINIUM
    Maui Kamaole #L-202

    Maui Kamaole #L-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $262 to $633/night

  57. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $556/night

  58. CONDOMINIUM
    Leinaala Oceanfront #104

    Leinaala Oceanfront #104

    Kihei, HI

    Pool
    FREE CANCELLATION

    $201 to $476/night

  59. CONDOMINIUM
    Maui Kamaole #I-215

    Maui Kamaole #I-215

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $377/night

  60. CONDOMINIUM
    Wailea Ekolu #805

    Wailea Ekolu #805

    Wailea, HI

    Pool
    FREE CANCELLATION

    $481/night

  61. CONDOMINIUM
    Maui Vista #2-418

    Maui Vista #2-418

    Kihei, HI

    Pool
    FREE CANCELLATION

    $289/night

  62. CONDOMINIUM
    Pacific Shores #A-303

    Pacific Shores #A-303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300/night

  63. CONDOMINIUM
    Maui Kamaole #H-211

    Maui Kamaole #H-211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405/night

  64. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $277/night

  65. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $927/night

  66. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $486/night

  67. CONDOMINIUM
    Waiohuli Beach Hale #B-206

    Waiohuli Beach Hale #B-206

    Kihei, HI

    Pool
    FREE CANCELLATION

    $277/night

  68. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $209/night

  69. CONDOMINIUM
    Kanai A Nalu #311

    Kanai A Nalu #311

    Maalaea, HI

    Pool
    FREE CANCELLATION

    $324/night

  70. CONDOMINIUM
    Leinaala Oceanfront #301

    Leinaala Oceanfront #301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $200 to $476/night

  71. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  72. CONDOMINIUM
    Maui Kamaole #L-105

    Maui Kamaole #L-105

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $245 to $581/night

  73. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $182 to $336/night

  74. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  75. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  76. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  77. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  78. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  79. CONDOMINIUM
    Kamaole Sands #8-310

    Kamaole Sands #8-310

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $289/night

  80. CONDOMINIUM
    Kihei Bay Surf #136

    Kihei Bay Surf #136

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $99 to $173/night

  81. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418/night

  82. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $266/night

  83. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,015/night

  84. CONDOMINIUM
    Maui Vista #2-402

    Maui Vista #2-402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $348/night

  85. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $347/night

  86. CONDOMINIUM
    Wailea Ekolu #1207

    Wailea Ekolu #1207

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $463/night

  87. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night