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. $188 to $502/night

    Kaleialoha #204

    Kaleialoha #204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $152 to $443/night

    Kaleialoha #305

    Kaleialoha #305

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  3. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  5. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  6. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  7. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  8. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $230 to $396/night

    Royal Kahana 107 1Bdrm

    Royal Kahana 107 1Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  10. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $274 to $409/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $152 to $502/night

    Kaleialoha #413

    Kaleialoha #413

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $204 to $423/night

    Royal Kahana 315

    Royal Kahana 315

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  14. $176 to $454/night

    Hale Ono Loa 101

    Hale Ono Loa 101

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $176 to $502/night

    Kaleialoha #114

    Kaleialoha #114

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $740 to $2,021/night

    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  17. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  18. $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
  19. $249 to $368/night

    Papakea A108

    Papakea A108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  20. $188 to $502/night

    Kaleialoha #113

    Kaleialoha #113

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $191 to $392/night

    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  22. $408 to $861/night

    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  23. $494 to $781/night

    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua Bay Villa 30B1 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  24. $428 to $484/night

    Kahana Sunset F4

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  25. $428 to $484/night

    Kahana Sunset F2

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  26. $236 to $304/night

    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  27. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  28. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $426 to $619/night

    Ilikai #1743

    Ilikai #1743

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  33. $292 to $337/night

    Casa De Emdeko 317

    Casa De Emdeko 317

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $377 to $591/night

    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  36. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $451 to $571/night

    Hale Ono Loa 409

    Hale Ono Loa 409

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $324 to $531/night

    Kulakane 307

    Kulakane 307

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $219 to $438/night

    Maui Kai 206

    Maui Kai 206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $250 to $350/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $290 to $435/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $220 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $169 to $261/night

    Kahana Reef 303

    Kahana Reef 303

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $311 to $738/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $324 to $588/night

    Sands of Kahana 316

    Sands of Kahana 316

    2 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $293 to $361/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $274 to $336/night

    Honokeana Cove 103

    Honokeana Cove 103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $136 to $289/night

    Kahana Reef 103

    Kahana Reef 103

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. $344 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $176 to $249/night

    Royal Kahana 618

    Royal Kahana 618

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. $185 to $316/night

    Kaleialoha 202

    Kaleialoha 202

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $231 to $449/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $152 to $443/night

    HOL 311

    HOL 311

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $299 to $456/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $216 to $235/night

    Lil Grass Shack-103

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  62. $371 to $484/night

    Kahana Sunset F6

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  63. $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
  64. $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
  65. $259 to $428/night

    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  66. $354 to $436/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $362 to $977/night

    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  68. $140 to $413/night

    HOL #216

    HOL #216

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $248 to $361/night

    Kaleialoha 309

    Kaleialoha 309

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $199 to $306/night

    Maui Kai 605

    Maui Kai 605

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $455 to $1,035/night

    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  72. $207 to $620/night

    HOL 119

    HOL 119

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  73. $188 to $502/night

    Kaleialoha #207

    Kaleialoha #207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $164 to $502/night

    Kaleialoha #214

    Kaleialoha #214

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  77. $363 to $985/night

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  79. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  80. $191 to $355/night

    Royal Kahana 702

    Royal Kahana 702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  81. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  84. $341 to $413/night

    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  86. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $176 to $502/night

    Kaleialoha #115

    Kaleialoha #115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $306/night

    Kulakane 304

    Kulakane 304

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  91. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  93. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  94. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  95. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  96. $594 to $1,063/night

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  97. $164 to $502/night

    Kaleialoha #315

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  99. $311 to $365/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $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