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. $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
  2. $360 to $557/night

    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  3. $124 to $174/night

    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $142 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  5. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  6. $152 to $219/night

    Nani Kai Hale 307

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  7. $349 to $585/night

    A5-2 Beachfront Loft Suite

    A5-2 Beachfront Loft Suite

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  8. $141 to $197/night

    Nani Kai Hale # 301

    Nani Kai Hale # 301

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $362 to $422/night

    Pali Ke Kua 203

    Pali Ke Kua 203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $152 to $219/night

    Nani Kai Hale # 405

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  11. $311 to $564/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  12. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  13. $188 to $258/night

    107

    107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  14. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  15. $201 to $274/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  16. $513 to $1,002/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $193 to $359/night

    Kaanapali Shores Studio 742

    Kaanapali Shores Studio 742

    Studio BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  18. $362 to $512/night

    Puu Poa 107

    Puu Poa 107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $392 to $542/night

    Puu Poa 310

    Puu Poa 310

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $253 to $301/night

    Cliffs 8205

    Cliffs 8205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $253 to $309/night

    Kahana Sunset B1

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  22. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  23. $276 to $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  24. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  25. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  26. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  27. $428 to $484/night

    Kahana Sunset A5

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  28. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  29. $276 to $332/night

    Kahana Sunset E8

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  30. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  31. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  32. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  33. $262 to $547/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  34. $273 to $589/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $186 to $334/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  37. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  38. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  39. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  41. $473 to $868/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $161 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $163 to $239/night

    Hale Pineapple

    Hale Pineapple

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  44. $275 to $413/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $227 to $257/night

    Wailua Bay View 204

    Wailua Bay View 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $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
  47. $443 to $861/night

    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  48. $432 to $861/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  49. $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
  50. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  52. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

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

    KIHEI BEACH, #305*

    KIHEI BEACH, #305*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  54. $212 to $309/night

    KIHEI BEACH, #306

    KIHEI BEACH, #306

    1 BedroomBathroomsSleeps 3
    5 nights minstay
    Pool
  55. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  56. $190 to $387/night

    SUGAR BEACH RESORT, #430^

    SUGAR BEACH RESORT, #430^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  57. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  58. $223 to $258/night

    KEALIA RESORT, #609**

    KEALIA RESORT, #609**

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
  59. $193 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $202 to $387/night

    SUGAR BEACH RESORT, #418

    SUGAR BEACH RESORT, #418

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  61. $470 to $953/night

    WAILEA ELUA, #0105

    WAILEA ELUA, #0105

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  62. $190 to $387/night

    SUGAR BEACH RESORT, #524^

    SUGAR BEACH RESORT, #524^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  63. $329 to $528/night

    WAILEA ELUA, #0807

    WAILEA ELUA, #0807

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
  64. $437 to $953/night

    WAILEA ELUA, #0802

    WAILEA ELUA, #0802

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  65. $347 to $443/night

    WAILEA EKAHI, #22D

    WAILEA EKAHI, #22D

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  66. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  67. $190 to $387/night

    SUGAR BEACH RESORT, #531

    SUGAR BEACH RESORT, #531

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  68. $235 to $324/night

    KIHEI BEACH, #103

    KIHEI BEACH, #103

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  69. $202 to $387/night

    SUGAR BEACH RESORT, #PH23

    SUGAR BEACH RESORT, #PH23

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  70. $292 to $526/night

    MAALAEA SURF, #C-8

    MAALAEA SURF, #C-8

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  71. $627 to $1,065/night

    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  72. $212 to $309/night

    KIHEI BEACH, #403

    KIHEI BEACH, #403

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  73. $223 to $309/night

    KIHEI BEACH, #506^

    KIHEI BEACH, #506^

    1 BedroomBathroomsSleeps 2
    7 nights minstay
    Pool
  74. $1,514 to $2,750/night

    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
  75. $190 to $387/night

    SUGAR BEACH RESORT, #136^

    SUGAR BEACH RESORT, #136^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  76. $538 to $1,065/night

    WAILEA ELUA, #0202*

    WAILEA ELUA, #0202*

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  77. $178 to $309/night

    KIHEI BEACH, #303

    KIHEI BEACH, #303

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  78. $448 to $1,065/night

    WAILEA ELUA, #0902

    WAILEA ELUA, #0902

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  79. $571 to $1,789/night

    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  80. $397 to $1,209/night

    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  81. $397 to $717/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  82. $248 to $292/night

    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  83. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  84. $299 to $488/night

    WAILEA ELUA, #0106

    WAILEA ELUA, #0106

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
  85. $221 to $506/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $186 to $331/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $344 to $676/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $211 to $364/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $219 to $455/night

    Mahana 602

    Mahana 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $315 to $686/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $508 to $1,789/night

    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  93. $181 to $331/night

    Hale Ono Loa 106

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. $504 to $896/night

    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  95. $263 to $421/night

    KIHEI BEACH, #309

    KIHEI BEACH, #309

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  96. $362 to $977/night

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  97. $167 to $296/night

    Kaleialoha 112

    Kaleialoha 112

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  98. $855 to $1,319/night

    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  99. $470 to $953/night

    WAILEA ELUA, #2010

    WAILEA ELUA, #2010

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  100. $470 to $953/night

    WAILEA ELUA, #0801*

    WAILEA ELUA, #0801*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub