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. $168 to $731/night

    Waikiki Banyan 2206-2 *Legal Vacation Rental

    Waikiki Banyan 2206-2 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  2. $717 to $904/night

    Hale Koaniani

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  3. $204 to $312/night

    Valley Isle 110

    Valley Isle 110

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $251 to $432/night

    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  5. $281 to $311/night

    Kulakane 306

    Kulakane 306

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  6. $287 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
  7. $211 to $286/night

    Maalaea Banyans 203

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $417 to $985/night

    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  9. $218 to $431/night

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  10. $161 to $334/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $313 to $529/night

    Napili Point B44

    Napili Point B44

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $126 to $291/night

    Kulakane 211

    Kulakane 211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $203 to $374/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $374 to $765/night

    Kaanapali Shores 515

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $200 to $289/night

    Napili Shores B214

    Napili Shores B214

    Studio BathroomSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $419 to $725/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $319 to $829/night

    Hale Ono Loa 109

    Hale Ono Loa 109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $301 to $690/night

    Napili Point A9

    Napili Point A9

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $150 to $336/night

    Valley Isle 902

    Valley Isle 902

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $199 to $456/night

    Kaleialoha 406

    Kaleialoha 406

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $410 to $926/night

    Mahana 501

    Mahana 501

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $161 to $265/night

    Papakea G301

    Papakea G301

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $263 to $765/night

    Kaanapali Shores 613

    Kaanapali Shores 613

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $438 to $695/night

    Sands of Kahana 354

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $757 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $229 to $299/night

    Hula Hideaway-303

    Hula Hideaway-303

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $459 to $1,037/night

    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  28. $256 to $436/night

    Kuleana 208 1 Bdrm

    Kuleana 208 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  29. $180 to $343/night

    Kuleana 321

    Kuleana 321

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $290 to $456/night

    Mahana 307

    Mahana 307

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $153 to $378/night

    Hale Ono Loa 214

    Hale Ono Loa 214

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  32. $141 to $208/night

    Nani Kai Hale # 507

    Nani Kai Hale # 507

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  33. $208 to $389/night

    Kahana Reef 201

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $156 to $405/night

    Wailea Ekahi 36C

    Wailea Ekahi 36C

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $179 to $376/night

    Hoyochi Nikko 108

    Hoyochi Nikko 108

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $331 to $709/night

    Mahana 1008

    Mahana 1008

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $255 to $515/night

    Paki Maui 123

    Paki Maui 123

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $190 to $731/night

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  39. $152 to $219/night

    Nani Kai Hale # 405

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. $531 to $969/night

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  41. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  42. $513 to $966/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $350/night

    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  44. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  45. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  46. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $234 to $683/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $350 to $686/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $224 to $516/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $200 to $438/night

    Lauloa 105

    Lauloa 105

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $181 to $331/night

    Hale Ono Loa 106

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $120 to $294/night

    Kaleialoha 402

    Kaleialoha 402

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $246 to $509/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $391 to $654/night

    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $149 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $219 to $596/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $150 to $333/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $152 to $219/night

    Nani Kai Hale 307

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  60. $141 to $197/night

    Nani Kai Hale # 301

    Nani Kai Hale # 301

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  61. $281 to $311/night

    Kulakane 304

    Kulakane 304

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  62. $199 to $325/night

    Hale Ono Loa 402

    Hale Ono Loa 402

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  63. $186 to $334/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $229 to $455/night

    Mahana 602

    Mahana 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $275 to $624/night

    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $204 to $235/night

    Lil Grass Shack-103

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  67. $152 to $219/night

    Nani Kai Hale # 304

    Nani Kai Hale # 304

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  68. $197 to $264/night

    Nani Kai Hale # 302

    Nani Kai Hale # 302

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  69. $141 to $208/night

    Nani Kai Hale # 601

    Nani Kai Hale # 601

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. $203 to $276/night

    Nani Kai Hale # 502

    Nani Kai Hale # 502

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  71. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  72. $299 to $337/night

    Casa De Emdeko 317

    Casa De Emdeko 317

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $313 to $524/night

    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  75. $263 to $522/night

    Oceanfront 3BR, Breathtaking Views

    Oceanfront 3BR, Breathtaking Views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  76. $162 to $452/night

    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $188 to $438/night

    Maui Kai 206

    Maui Kai 206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $226 to $430/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $206 to $326/night

    Maui Kai 108

    Maui Kai 108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $199 to $308/night

    Maui Kai 605

    Maui Kai 605

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $336 to $746/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $249 to $614/night

    Hololani A303

    Hololani A303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $124 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $235 to $531/night

    Kulakane 307

    Kulakane 307

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $136 to $336/night

    Kahana Reef 106

    Kahana Reef 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  86. $188 to $463/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $199 to $448/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  88. $513 to $1,789/night

    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  89. $176 to $454/night

    Hale Ono Loa 101

    Hale Ono Loa 101

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $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
  92. $188 to $344/night

    Polynesian Shores 111

    Polynesian Shores 111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  93. $226 to $453/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $589 to $1,363/night

    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  95. $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
  96. $216 to $470/night

    Hololani A701

    Hololani A701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  97. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $144 to $304/night

    Kaleialoha 202

    Kaleialoha 202

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $186 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION