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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night

  2. CONDOMINIUM
    Kihei Beach Unit #603

    Kihei Beach Unit #603

    Kihei, HI

    Pool

    $223 to $309/night

  3. CONDOMINIUM
    Royal Mauian Unit #315

    Royal Mauian Unit #315

    Kihei, HI

    Pool

    $437 to $605/night

  4. CONDOMINIUM
    Wailea Elua Unit #1002

    Wailea Elua Unit #1002

    Wailea, HI

    Pool

    $762 to $1,515/night

  5. CONDOMINIUM
    Wailea Ekahi Unit #33B

    Wailea Ekahi Unit #33B

    Kihei, HI

    Pool

    $280 to $414/night

  6. CONDOMINIUM
    Wailea Elua Unit #0702

    Wailea Elua Unit #0702

    Wailea, HI

    Pool

    $459 to $953/night

  7. CONDOMINIUM
    Kihei Surfside, #612

    Kihei Surfside, #612

    Kihei, HI

    Pool

    $185 to $427/night

  8. CONDOMINIUM
    Waiohuli Beach Hale #D-121

    Waiohuli Beach Hale #D-121

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  9. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  10. CONDOMINIUM
    Maui Kamaole #I-215

    Maui Kamaole #I-215

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $377/night

  11. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  12. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  13. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $263/night

  14. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  15. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $465 to $485/night

  16. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $556/night

  17. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $501/night

  18. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $162 to $413/night

  19. CONDOMINIUM
    Waiohuli Beach Hale #B-108

    Waiohuli Beach Hale #B-108

    Kihei, HI

    Pool
    FREE CANCELLATION

    $277/night

  20. CONDOMINIUM
    Keawakapu Views #206

    Keawakapu Views #206

    Kihei, HI

    FREE CANCELLATION

    $157 to $261/night

  21. CONDOMINIUM
    Maui Vista #2-418

    Maui Vista #2-418

    Kihei, HI

    Pool
    FREE CANCELLATION

    $202 to $289/night

  22. CONDOMINIUM
    Kihei Akahi #C-217

    Kihei Akahi #C-217

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $242/night

  23. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  24. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $1,219/night

  25. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  26. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night

  27. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418/night

  28. CONDOMINIUM
    Wailea Ekolu #205

    Wailea Ekolu #205

    Wailea, HI

    Pool
    FREE CANCELLATION

    $522/night

  29. CONDOMINIUM
    Waiohuli Beach Hale #D-122

    Waiohuli Beach Hale #D-122

    Kihei, HI

    Pool
    FREE CANCELLATION

    $277/night

  30. CONDOMINIUM
    309

    309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $393/night

  31. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $347/night

  32. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $182/night

  33. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $486/night

  34. CONDOMINIUM
    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    Kapaa, HI

    Pool

    $311 to $386/night

  35. CONDOMINIUM
    Sugar Beach Resort, #328

    Sugar Beach Resort, #328

    Kihei, HI

    Pool

    $202 to $387/night

  36. CONDOMINIUM
    Sugar Beach Resort, #535

    Sugar Beach Resort, #535

    Kihei, HI

    Pool

    $365 to $627/night

  37. CONDOMINIUM
    Kihei Beach Unit #110

    Kihei Beach Unit #110

    Kihei, HI

    Pool

    $263 to $421/night

  38. CONDOMINIUM
    Wailea Elua Unit #0909

    Wailea Elua Unit #0909

    Wailea, HI

    Pool

    $358 to $661/night

  39. CONDOMINIUM
    Wailea Ekolu Unit #312

    Wailea Ekolu Unit #312

    Wailea, HI

    Pool

    $190 to $382/night

  40. CONDOMINIUM
    Kealia Resort Unit #304

    Kealia Resort Unit #304

    Kihei, HI

    Pool

    $223 to $321/night

  41. CONDOMINIUM
    Kihei Surfside, #411

    Kihei Surfside, #411

    Kihei, HI

    Pool

    $208 to $448/night

  42. CONDOMINIUM
    Makena Surf Resort, #B-204

    Makena Surf Resort, #B-204

    Makena, HI

    Pool

    $773 to $1,319/night

  43. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458/night

  44. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $568/night

  45. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    Wailea, HI

    Pool
    FREE CANCELLATION

    $302 to $725/night

  46. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $616/night

  47. CONDOMINIUM
    Kepuhi Beach Condo 1153

    Kepuhi Beach Condo 1153

    Maunaloa, HI

    Pool
    FREE CANCELLATION

    $135/night

  48. CONDOMINIUM
    Ke Nani Kai Condo 260

    Ke Nani Kai Condo 260

    Maunaloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $169/night

  49. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  50. CONDOMINIUM
    Kihei Bay Vista #C-106

    Kihei Bay Vista #C-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  51. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $183/night

  52. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $273/night

  53. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $447/night

  54. CONDOMINIUM
    Grand Champions #86

    Grand Champions #86

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $325/night

  55. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $521/night

  56. CONDOMINIUM
    Hale Kamaole #201

    Hale Kamaole #201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $300 to $358/night

  57. CONDOMINIUM
    Wailea Ekolu #501

    Wailea Ekolu #501

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $521/night

  58. CONDOMINIUM
    Sealodge G4

    Sealodge G4

    Princeville, HI

    Pool
    FREE CANCELLATION

    $182 to $257/night

  59. CONDOMINIUM
    Wailea Elua Unit #1403

    Wailea Elua Unit #1403

    Wailea, HI

    Pool

    $931 to $1,459/night

  60. CONDOMINIUM
    Wailea Elua Unit #1309

    Wailea Elua Unit #1309

    Wailea, HI

    Pool

    $634 to $896/night

  61. CONDOMINIUM
    Kihei Surfside, #205

    Kihei Surfside, #205

    Kihei, HI

    Pool

    $185 to $427/night

  62. CONDOMINIUM
    Sugar Beach Resort #PH23

    Sugar Beach Resort #PH23

    Kihei, HI

    Pool Hot Tub

    $202 to $387/night

  63. HOUSE
    Indo Lotus Beach House

    Indo Lotus Beach House

    Wailea, HI

    Hot Tub

    $1,234 to $2,694/night

  64. CONDOMINIUM
    Kihei Surfside Unit #111

    Kihei Surfside Unit #111

    Kihei, Maui, HI

    Pool Pets OK

    $185 to $427/night

  65. CONDOMINIUM
    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    Wailea, HI

    Pool

    $448 to $896/night

  66. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    Wailea, HI

    Pool

    $494 to $1,065/night

  67. CONDOMINIUM
    Sugar Beach Resort, #418

    Sugar Beach Resort, #418

    Kihei, HI

    Pool

    $202 to $387/night

  68. CONDOMINIUM
    Makena Surf Resort, #G-101

    Makena Surf Resort, #G-101

    Makena, HI

    Pool

    $775 to $1,094/night

  69. CONDOMINIUM
    Sugar Beach Resort, #524

    Sugar Beach Resort, #524

    Kihei, HI

    Pool

    $190 to $387/night

  70. CONDOMINIUM
    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    Honolulu, HI

    FREE CANCELLATION

    $178 to $248/night

  71. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $219/night

  72. CONDOMINIUM
    Kihei Akahi #DG06

    Kihei Akahi #DG06

    Kihei, HI

    Pool
    FREE CANCELLATION

    $126 to $231/night

  73. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  74. CONDOMINIUM
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $320 to $703/night

  75. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $491/night

  76. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  77. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $308/night

  78. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  79. CONDOMINIUM
    Waiohuli Beach Hale #D-120

    Waiohuli Beach Hale #D-120

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  80. CONDOMINIUM
    Maui Vista #2-423

    Maui Vista #2-423

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $347/night

  81. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  82. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  83. CONDOMINIUM
    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  84. CONDOMINIUM
    Wailea Ekolu #804

    Wailea Ekolu #804

    Wailea, HI

    Pool
    FREE CANCELLATION

    $405/night

  85. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  86. CONDOMINIUM
    Maui Kamaole #M-105

    Maui Kamaole #M-105

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $339/night

  87. CONDOMINIUM
    131

    131

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night