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. $386 to $522/night

    Moloa'a Bay Cottage

    Moloa'a Bay Cottage

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
  2. $456 to $594/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  3. $402 to $524/night

    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $542 to $555/night

    Hale Pahukoa

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  5. $256 to $436/night

    Kuleana 622 1Bdrm

    Kuleana 622 1Bdrm

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  6. $135 to $411/night

    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $256 to $436/night

    Kuleana 713 1 Bdrm

    Kuleana 713 1 Bdrm

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  8. $344 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $299 to $440/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $218 to $324/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  11. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  12. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $406 to $599/night

    Hale Ono Loa 409

    Hale Ono Loa 409

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $204 to $384/night

    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $263 to $421/night

    KIHEI BEACH, #409

    KIHEI BEACH, #409

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  17. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $293 to $356/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $274 to $409/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  20. $305 to $448/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  21. $249 to $346/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $202 to $387/night

    SUGAR BEACH RESORT, #518^

    SUGAR BEACH RESORT, #518^

    1 Bedroom BathroomSleeps 2
    7 nights minstay
    Pool Hot Tub
  23. $326 to $350/night

    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  24. $219 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $574 to $1,347/night

    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  26. $397 to $551/night

    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $353 to $421/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $191 to $410/night

    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. $482 to $1,009/night

    WAILEA ELUA, #0702

    WAILEA ELUA, #0702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  31. $393 to $560/night

    SUGAR BEACH RESORT, #PH12

    SUGAR BEACH RESORT, #PH12

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  32. $897 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  33. $448 to $897/night

    WAILEA ELUA, #2106

    WAILEA ELUA, #2106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  34. $504 to $896/night

    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  35. $291 to $425/night

    WAILEA EKAHI, #33B

    WAILEA EKAHI, #33B

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  36. $212 to $309/night

    KIHEI BEACH, #406^

    KIHEI BEACH, #406^

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  37. $456 to $660/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  38. $311 to $735/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $313 to $504/night

    WAILEA ELUA, #2101*

    WAILEA ELUA, #2101*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  40. $212 to $309/night

    KIHEI BEACH, #107

    KIHEI BEACH, #107

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  41. $212 to $309/night

    KIHEI BEACH, #207

    KIHEI BEACH, #207

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  42. $897 to $1,459/night

    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  43. $482 to $868/night

    WAILEA ELUA, #0302

    WAILEA ELUA, #0302

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  44. $292 to $526/night

    MAALAEA SURF, #G-7

    MAALAEA SURF, #G-7

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  45. $212 to $309/night

    KIHEI BEACH, #407

    KIHEI BEACH, #407

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  46. $223 to $309/night

    KIHEI BEACH, #603^

    KIHEI BEACH, #603^

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
  47. $241 to $326/night

    KIHEI BEACH, #606

    KIHEI BEACH, #606

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  48. $185 to $377/night

    WAILEA EKAHI, #24B^

    WAILEA EKAHI, #24B^

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  49. $219 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $212 to $309/night

    KIHEI BEACH, #404

    KIHEI BEACH, #404

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  52. $775 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  53. $212 to $309/night

    KIHEI BEACH, #405

    KIHEI BEACH, #405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  54. $296 to $448/night

    KIHEI BEACH, #501

    KIHEI BEACH, #501

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  55. $724 to $1,065/night

    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  56. $724 to $1,065/night

    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  57. $459 to $856/night

    WAILEA ELUA, #2003

    WAILEA ELUA, #2003

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  58. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  59. $223 to $309/night

    KIHEI BEACH, #307

    KIHEI BEACH, #307

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  60. $1,413 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  61. $231 to $445/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $236 to $636/night

    Kuleana 313

    Kuleana 313

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  65. $145 to $569/night

    Lahaina Shores 210

    Lahaina Shores 210

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  66. $488 to $658/night

    Sands of Kahana 354

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $311 to $428/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  68. $279 to $350/night

    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  69. $307 to $491/night

    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $255 to $455/night

    Kaleialoha 205

    Kaleialoha 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $426 to $795/night

    Hale Ono Loa 109

    Hale Ono Loa 109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  72. $281 to $474/night

    Hale Kai 208 2bdrm 2bath

    Hale Kai 208 2bdrm 2bath

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  73. $218 to $330/night

    Hoyochi Nikko #202

    Hoyochi Nikko #202

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  74. $390 to $958/night

    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $306 to $556/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $235 to $339/night

    Kuleana 321

    Kuleana 321

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $200 to $289/night

    Kulakane 211

    Kulakane 211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $200 to $320/night

    Valley Isle 902

    Valley Isle 902

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  79. $240 to $286/night

    Maalaea Banyans 203

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $418 to $666/night

    Kaanapali Shores 613

    Kaanapali Shores 613

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $200 to $316/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $418 to $666/night

    Kaanapali Shores 515

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $240 to $353/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  84. $220 to $356/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $436 to $715/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $259 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $443 to $1,022/night

    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  88. $251 to $384/night

    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  89. $329 to $490/night

    Island Sands 210

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $217 to $371/night

    Noelani 211- Modern, Upscale Ocean Front Condo

    Noelani 211- Modern, Upscale Ocean Front Condo

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $278 to $400/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $247 to $393/night

    MAALAEA SURF, #F-2

    MAALAEA SURF, #F-2

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  93. $571 to $1,065/night

    WAILEA ELUA, #2202*

    WAILEA ELUA, #2202*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  94. $421 to $627/night

    SUGAR BEACH RESORT, #540

    SUGAR BEACH RESORT, #540

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  95. $347 to $443/night

    WAILEA EKAHI, #22B

    WAILEA EKAHI, #22B

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  96. $223 to $321/night

    KEALIA RESORT, #304

    KEALIA RESORT, #304

    2 Bedrooms BathroomSleeps 4
    5 nights minstay
    Pool
  97. $421 to $627/night

    SUGAR BEACH RESORT, #535^

    SUGAR BEACH RESORT, #535^

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  98. $212 to $309/night

    KIHEI BEACH, #504

    KIHEI BEACH, #504

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  99. $246 to $379/night

    Hololani A204

    Hololani A204

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $378 to $564/night

    Kulakane 301

    Kulakane 301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION