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
    Sugar Beach #127

    Sugar Beach #127

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  2. CONDOMINIUM
    Sugar Beach #416

    Sugar Beach #416

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  3. CONDOMINIUM
    Lahaina Shores 210

    Lahaina Shores 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $138 to $569/night

  4. HOUSE
    Kauhale Makai #135

    Kauhale Makai #135

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $426/night

  5. CONDOMINIUM
    Waiohuli Beach Hale #B-205

    Waiohuli Beach Hale #B-205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  6. 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

  7. CONDOMINIUM
    Maalaea Surf Resort #C-3

    Maalaea Surf Resort #C-3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $244 to $418/night

  8. CONDOMINIUM
    Kauhale Makai #114

    Kauhale Makai #114

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $426/night

  9. CONDOMINIUM
    Hoyochi Nikko #202

    Hoyochi Nikko #202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $353/night

  10. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  11. CONDOMINIUM
    Sugar Beach #124

    Sugar Beach #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  12. CONDOMINIUM
    Sugar Beach #618

    Sugar Beach #618

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $318 to $426/night

  13. CONDOMINIUM
    Valley Isle #205

    Valley Isle #205

    Lahaina, HI

    Pool
    FREE CANCELLATION
  14. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  15. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  16. CONDOMINIUM
    Kauhale Makai #411

    Kauhale Makai #411

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $426/night

  17. CONDOMINIUM
    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  18. CONDOMINIUM
    Sugar Beach #522

    Sugar Beach #522

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  19. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  20. CONDOMINIUM
    Kaleialoha 406

    Kaleialoha 406

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $194 to $331/night

  21. CONDOMINIUM
    Sugar Beach #520

    Sugar Beach #520

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  22. CONDOMINIUM
    Maui Kai 1005

    Maui Kai 1005

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $508/night

  23. CONDOMINIUM
    Sugar Beach #223

    Sugar Beach #223

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $318 to $426/night

  24. CONDOMINIUM
    Sugar Beach #120

    Sugar Beach #120

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  25. CONDOMINIUM
    Kaleialoha #313

    Kaleialoha #313

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  26. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  27. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  28. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  29. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

  30. CONDOMINIUM
    Leinaala Oceanfront #105

    Leinaala Oceanfront #105

    Kihei, HI

    Pool
    FREE CANCELLATION

    $231 to $551/night

  31. CONDOMINIUM
    Waiohuli Beach Hale #D-225

    Waiohuli Beach Hale #D-225

    Kihei, HI

    Pool
    FREE CANCELLATION

    $201 to $477/night

  32. CONDOMINIUM
    Kona Isle C28

    Kona Isle C28

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $221 to $243/night

  33. CONDOMINIUM
    Kona Shores#130

    Kona Shores#130

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $198 to $219/night

  34. CONDOMINIUM
    Royal Kahana 1114 1 Bdrm

    Royal Kahana 1114 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $423/night

  35. CONDOMINIUM
    Kaleialoha #414

    Kaleialoha #414

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  36. CONDOMINIUM
    Waiohuli Beach Hale #D-223

    Waiohuli Beach Hale #D-223

    Kihei, HI

    Pool
    FREE CANCELLATION

    $189 to $451/night

  37. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $689 to $759/night

  38. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  39. CONDOMINIUM
    Kona Makai 6201

    Kona Makai 6201

    Kailua Kona, HI

    Pool Hot Tub

    $304 to $362/night

  40. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $243 to $384/night

  41. CONDOMINIUM
    Sea Village 1-205-Oceanfront

    Sea Village 1-205-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $194 to $279/night

  42. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $464/night

  43. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  44. CONDOMINIUM
    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  45. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  46. CONDOMINIUM
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $961/night

  47. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $451/night

  48. CONDOMINIUM
    Papakea G301

    Papakea G301

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $299/night

  49. CONDOMINIUM
    Waiohuli Beach Hale #A-203

    Waiohuli Beach Hale #A-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $255/night

  50. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $579/night

  51. CONDOMINIUM
    Waiohuli Beach Hale #C-111

    Waiohuli Beach Hale #C-111

    Kihei, HI

    Pool
    FREE CANCELLATION

    $232 to $394/night

  52. CONDOMINIUM
    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  53. 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

  54. CONDOMINIUM
    Valley Isle #1004

    Valley Isle #1004

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $414/night

  55. CONDOMINIUM
    Valley Isle #508

    Valley Isle #508

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $767/night

  56. CONDOMINIUM
    Valley Isle #808

    Valley Isle #808

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $209 to $609/night

  57. CONDOMINIUM
    Mahana Resort #1104

    Mahana Resort #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $606/night

  58. CONDOMINIUM
    Hale Mahina #B304

    Hale Mahina #B304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $396/night

  59. CONDOMINIUM
    Valley Isle #310

    Valley Isle #310

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $522/night

  60. CONDOMINIUM
    Royal Kahana #1112

    Royal Kahana #1112

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $162 to $447/night

  61. CONDOMINIUM
    Mahana Resort #1217

    Mahana Resort #1217

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $354 to $606/night

  62. CONDOMINIUM
    Mahana Resort #612

    Mahana Resort #612

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $476/night

  63. CONDOMINIUM
    Valley Isle #806

    Valley Isle #806

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $139 to $406/night

  64. CONDOMINIUM
    Mahana Resort #1103

    Mahana Resort #1103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $273 to $493/night

  65. CONDOMINIUM
    Hale Mahina #B102

    Hale Mahina #B102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $414/night

  66. CONDOMINIUM
    Valley Isle #509

    Valley Isle #509

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $440/night

  67. CONDOMINIUM
    Lahaina Roads #210

    Lahaina Roads #210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $168 to $414/night

  68. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  69. CONDOMINIUM
    Lahaina Shores #321

    Lahaina Shores #321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $435/night

  70. CONDOMINIUM
    Valley Isle #809

    Valley Isle #809

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $493/night

  71. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,558/night

  72. CONDOMINIUM
    Valley Isle #1204

    Valley Isle #1204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $383/night

  73. CONDOMINIUM
    Hale Mahina #A205

    Hale Mahina #A205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $414/night

  74. CONDOMINIUM
    Lokelani #B203

    Lokelani #B203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $640/night

  75. CONDOMINIUM
    Valley Isle #705

    Valley Isle #705

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $139 to $423/night

  76. CONDOMINIUM
    Valley Isle #208

    Valley Isle #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $255 to $767/night

  77. CONDOMINIUM
    Lahaina Roads #502

    Lahaina Roads #502

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $284 to $600/night

  78. CONDOMINIUM
    Napili Point #B-26

    Napili Point #B-26

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $574/night

  79. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $488 to $874/night

  80. CONDOMINIUM
    Hoyochi Nikko 108

    Hoyochi Nikko 108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $254 to $458/night

  81. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $208 to $471/night

  82. CONDOMINIUM
    Napili Point B44

    Napili Point B44

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $321 to $578/night

  83. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $359 to $1,016/night

  84. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $299/night

  85. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $801/night

  86. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $483/night

  87. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $406 to $624/night

  88. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $471/night

  89. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $198 to $355/night

  90. CONDOMINIUM
    Kona Isle #D31

    Kona Isle #D31

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $126 to $409/night

  91. CONDOMINIUM
    Royal Sea Cliff #415

    Royal Sea Cliff #415

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $748/night

  92. CONDOMINIUM
    Royal Sea Cliff #314

    Royal Sea Cliff #314

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $874/night

  93. CONDOMINIUM
    Kona Reef #A33

    Kona Reef #A33

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $536/night

  94. CONDOMINIUM
    Kona Isle #D1

    Kona Isle #D1

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $125 to $474/night

  95. CONDOMINIUM
    Kona Bali Kai #314- 2 Bedroom

    Kona Bali Kai #314- 2 Bedroom

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $565/night

  96. CONDOMINIUM
    Kahana Outrigger #2B1

    Kahana Outrigger #2B1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $551 to $1,015/night

  97. CONDOMINIUM
    Mahana Resort #705

    Mahana Resort #705

    Lahaina, HI

    FREE CANCELLATION

    $331 to $737/night

  98. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  99. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  100. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Kaanapali, HI

    Pool Hot Tub

    $531 to $1,999/night