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. $175 to $410/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $350 to $688/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $156 to $410/night

    Wailea Ekahi 49A

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $122 to $316/night

    Pono Kai H207

    Pono Kai H207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $330 to $625/night

    Hanalei Bay Resort 8133/4

    Hanalei Bay Resort 8133/4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $106 to $253/night

    Cliffs 4209

    Cliffs 4209

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $96 to $260/night

    Sealodge B6

    Sealodge B6

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $241 to $526/night

    Villas of Kamalii 44

    Villas of Kamalii 44

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $121 to $348/night

    Ali'i Kai 6102

    Ali'i Kai 6102

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $145 to $314/night

    Ali'i Kai 4303

    Ali'i Kai 4303

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $121 to $262/night

    Cliffs 5205

    Cliffs 5205

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $154 to $332/night

    Ali'i Kai 7204

    Ali'i Kai 7204

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $231 to $275/night

    Sealodge D1

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  14. $188 to $502/night

    Kaleialoha #207

    Kaleialoha #207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $156 to $240/night

    Valley Isle #1106

    Valley Isle #1106

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  16. $250 to $575/night

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in the Heart

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in th...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  17. $262 to $537/night

    Kona Plaza 112

    Kona Plaza 112

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  18. $1,063 to $4,054/night

    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  19. $145 to $358/night

    Ilikai Tower 735

    Ilikai Tower 735

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  20. $128 to $345/night

    Ilikai Tower 611

    Ilikai Tower 611

    1 Bedroom BathroomSleeps 3
    1 night minstay
    Pool
    FREE CANCELLATION
  21. $133 to $380/night

    Ilikai Tower 827

    Ilikai Tower 827

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  22. $145 to $353/night

    Ilikai Tower 333

    Ilikai Tower 333

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  23. $150 to $473/night

    Ilikai Tower 2136

    Ilikai Tower 2136

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  24. $145 to $406/night

    Ilikai Tower 527

    Ilikai Tower 527

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  25. $154 to $445/night

    Ilikai Tower 814

    Ilikai Tower 814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  26. $157 to $400/night

    Ilikai Tower 839

    Ilikai Tower 839

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  27. $164 to $480/night

    Sea Village #3318

    Sea Village #3318

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $164 to $480/night

    Country Club Villas #208

    Country Club Villas #208

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $128 to $439/night

    THE SHORES OF MAUI #223

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $175 to $536/night

    Kona Bali Kai #206- 2 Bedroom

    Kona Bali Kai #206- 2 Bedroom

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $269 to $705/night

    Fairway Villas #K1 at the Waikoloa Beach Resort

    Fairway Villas #K1 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $625 to $1,651/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $144 to $375/night

    White Sands Village #135

    White Sands Village #135

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $188 to $641/night

    WAILEA EKOLU #203

    WAILEA EKOLU #203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $119 to $339/night

    Keauhou Resort #111

    Keauhou Resort #111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $184 to $536/night

    Vista Waikoloa C305

    Vista Waikoloa C305

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $148 to $453/night

    White Sands Village #206

    White Sands Village #206

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $119 to $339/night

    Keauhou Akahi #312

    Keauhou Akahi #312

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $149 to $463/night

    Alii Villas #132

    Alii Villas #132

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $300 to $480/night

    White Sands Village #201

    White Sands Village #201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $250 to $625/night

    Ilima Suite at The Ilikai (Unit 1226)

    Ilima Suite at The Ilikai (Unit 1226)

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $349 to $1,073/night

    Mauna Lani Golf Villas #N4

    Mauna Lani Golf Villas #N4

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $193 to $574/night

    Kona Nalu #302

    Kona Nalu #302

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $719 to $1,411/night

    Nai'a Hale

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  46. $154 to $451/night

    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $198 to $579/night

    Kanaloa At Kona #3001

    Kanaloa At Kona #3001

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $119 to $350/night

    Casa De Emdeko #334

    Casa De Emdeko #334

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  49. $219 to $650/night

    Kanaloa At Kona #3701

    Kanaloa At Kona #3701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $236 to $776/night

    Sea Village #4114

    Sea Village #4114

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $250 to $734/night

    Kona Reef #D31

    Kona Reef #D31

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $347 to $389/night

    Keauhou Kona Surf & Racket Club Townhouse #4

    Keauhou Kona Surf & Racket Club Townhouse #4

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  53. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $106 to $273/night

    Paki Maui 316

    Paki Maui 316

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $211 to $324/night

    Napili Shores E243

    Napili Shores E243

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $389 to $625/night

    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  58. $250 to $326/night

    Casa De Emdeko 111

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $152 to $244/night

    Kona Isle B31

    Kona Isle B31

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  60. $149 to $169/night

    Kahana Reef 122

    Kahana Reef 122

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    FREE CANCELLATION
  61. $188 to $258/night

    207

    207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $258 to $340/night

    340

    340

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  63. $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
  64. $369 to $688/night

    Kapalua Golf Villa 23V3 Ocean View

    Kapalua Golf Villa 23V3 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  65. $589 to $1,616/night

    Ho'o Maluhia

    Ho'o Maluhia

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  66. $780 to $1,395/night

    Hale Poola

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  67. $201 to $296/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  68. $261 to $486/night

    Puamana 52-3

    Puamana 52-3

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $254 to $524/night

    International Colony Club 20

    International Colony Club 20

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $99 to $156/night

    Sandpiper 121B

    Sandpiper 121B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $241 to $244/night

    Country Club Villas#115

    Country Club Villas#115

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  73. $204 to $238/night

    Mauna Kai 5A

    Mauna Kai 5A

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. $542 to $1,330/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  75. $688 to $1,623/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  76. $227 to $293/night

    Alii Kai 3103

    Alii Kai 3103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  77. $181 to $470/night

    Eldorado G205

    Eldorado G205

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $156 to $274/night

    Hale Ono Loa 401

    Hale Ono Loa 401

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $193 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. $192 to $247/night

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  82. $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
  83. $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
  84. $357 to $741/night

    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $258 to $340/night

    221

    221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $188 to $299/night

    Napili Shores E240

    Napili Shores E240

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $526 to $860/night

    Papakea K-402

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $200 to $438/night

    Lauloa 105

    Lauloa 105

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $181 to $331/night

    Hale Ono Loa 106

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $556 to $1,063/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  91. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  92. $191 to $359/night

    Royal Kahana 318

    Royal Kahana 318

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  93. $269 to $461/night

    Kapalua Golf Villa 14T

    Kapalua Golf Villa 14T

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $231 to $456/night

    Hale Ono Loa 102

    Hale Ono Loa 102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $120 to $294/night

    Kaleialoha 402

    Kaleialoha 402

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  97. $233 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $246 to $518/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $110 to $203/night

    Discovery Bay 2502

    Discovery Bay 2502

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  100. $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