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. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  2. $485 to $652/night

    Hale Ulu'wehi

    Hale Ulu'wehi

    4 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  3. $162 to $584/night

    Kona Alii 608

    Kona Alii 608

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  5. $204 to $370/night

    Honua Kai 322

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $397 to $1,209/night

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  7. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $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
  9. $186 to $214/night

    Kahana Sunset B3B

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  10. $428 to $484/night

    Kahana Sunset F2

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  11. $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
  12. $178 to $319/night

    Hale Ono Loa #316

    Hale Ono Loa #316

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  13. $174 to $299/night

    Eldorado J111

    Eldorado J111

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  14. $164 to $502/night

    Kaleialoha #413

    Kaleialoha #413

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $140 to $239/night

    Aina Nalu K 205

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $214 to $270/night

    Bay Villa 33B2

    Bay Villa 33B2

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  17. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $294 to $494/night

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  19. $339 to $861/night

    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  20. $276 to $332/night

    Kahana Sunset D8

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  21. $428 to $484/night

    Kahana Sunset F4

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  22. $525 to $869/night

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  23. $253 to $366/night

    Kahana Sunset B3

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  24. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $204 to $235/night

    Lil Grass Shack-103

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  26. $218 to $296/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  27. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  28. $309 to $366/night

    Kahana Sunset B7

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  29. $253 to $309/night

    Kahana Sunset D10

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  30. $219 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  31. $181 to $358/night

    Aina Nalu A 201

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  34. $501 to $557/night

    Sands Of Kahana 474

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  35. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $276 to $332/night

    Kahana Sunset D2

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  37. $197 to $248/night

    Ridge Villa 1422

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  38. $152 to $443/night

    HOL 311

    HOL 311

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $276 to $332/night

    Kahana Sunset C7

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  40. $176 to $502/night

    Kaleialoha #114

    Kaleialoha #114

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $296 to $521/night

    International Colony Club #18

    International Colony Club #18

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  42. $369 to $594/night

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  43. $274 to $465/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $140 to $413/night

    HOL #216

    HOL #216

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $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
  46. $582 to $1,325/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  47. $371 to $484/night

    Kahana Sunset F6

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  48. $236 to $304/night

    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  49. $184 to $353/night

    Pohailani #133

    Pohailani #133

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  50. $249 to $312/night

    Malolo Cottage

    Malolo Cottage

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  51. $236 to $368/night

    Papakea A108

    Papakea A108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  52. $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
  53. $208 to $253/night

    Sands Of Kahana 231

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  54. $188 to $502/night

    Kaleialoha #204

    Kaleialoha #204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $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
  56. $274 to $686/night

    Kaanapali Royal N102

    Kaanapali Royal N102

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $2,203 to $4,290/night

    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  58. $293 to $337/night

    Casa De Emdeko 211

    Casa De Emdeko 211

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $305 to $337/night

    Casa De Emdeko 317

    Casa De Emdeko 317

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. $234 to $239/night

    Casa De Emdeko 332

    Casa De Emdeko 332

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  61. $1,109 to $1,111/night

    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $286 to $478/night

    Hale Ohana Aloha

    Hale Ohana Aloha

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  63. $102 to $162/night

    AV 302

    AV 302

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  64. $269 to $469/night

    Kapalua Ridge Villa 611 Ocean View

    Kapalua Ridge Villa 611 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  65. $152 to $443/night

    Kaleialoha #305

    Kaleialoha #305

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $478 to $1,673/night

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  68. $542 to $1,234/night

    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  69. $844 to $2,781/night

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  70. $1,261 to $4,648/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  71. $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
  72. $197 to $291/night

    Kona Plaza#402

    Kona Plaza#402

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $406 to $781/night

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  74. $314 to $764/night

    Poipu Crater

    Poipu Crater

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  75. $476 to $1,372/night

    Hallor House TVNC #5147

    Hallor House TVNC #5147

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  76. $690 to $1,609/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  77. $1,165 to $3,966/night

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  78. $416 to $786/night

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To Beach

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  79. $3,248 to $5,568/night

    Wailea Inn Maui

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 35
    2 nights minstay
  80. $1,734 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  81. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  82. $4,194 to $7,190/night

    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  83. $193 to $255/night

    Holoholo ku Waimea

    Holoholo ku Waimea

    3 BedroomsBathroomsSleeps 6
    14 nights minstay
    FREE CANCELLATION
  84. $315 to $495/night

    Diamond Head Beach Hotel 501

    Diamond Head Beach Hotel 501

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $321 to $444/night

    Diamond Head Beach Hotel 601

    Diamond Head Beach Hotel 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  86. $124 to $174/night

    Waikiki Grand 411

    Waikiki Grand 411

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $501 to $619/night

    Sands of Kahana 366

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  88. $204 to $312/night

    Valley Isle 110

    Valley Isle 110

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $362 to $861/night

    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  90. $513 to $977/night

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  91. $781 to $1,219/night

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  92. $428 to $484/night

    Kahana Sunset A4

    Kahana Sunset A4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  93. $444 to $557/night

    Sands Of Kahana 275

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  94. $309 to $366/night

    Kahana Sunset B6

    Kahana Sunset B6

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pool
  95. $173 to $296/night

    Noelani #219

    Noelani #219

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $501 to $1,093/night

    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  97. $240 to $319/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  98. $278 to $341/night

    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $366 to $501/night

    Bay Villa 37G4

    Bay Villa 37G4

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  100. $218 to $330/night

    Hoyochi Nikko #202

    Hoyochi Nikko #202

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION