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. $485 to $652/night

    Hale Ulu'wehi

    Hale Ulu'wehi

    4 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  2. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  3. $175/night

    Waikiki Beach Walk 1 Bedroom

    Waikiki Beach Walk 1 Bedroom

    Multiple Units Available
    3 nights minstay
    Pool Hot Tub
  4. $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
  5. $221 to $431/night

    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $249 to $312/night

    Malolo Cottage

    Malolo Cottage

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  7. $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
  8. $102 to $162/night

    AV 302

    AV 302

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  9. $231 to $569/night

    Kapalua Ridge Villa #311

    Kapalua Ridge Villa #311

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $219 to $313/night

    Keawakapu 208

    Keawakapu 208

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  11. $124 to $438/night

    Maui Kai 206

    Maui Kai 206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $124 to $329/night

    Kahana Reef 106

    Kahana Reef 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  13. $281 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $286 to $478/night

    Hale Ohana Aloha

    Hale Ohana Aloha

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  15. $134 to $219/night

    Island Surf 306

    Island Surf 306

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $211 to $399/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $146 to $324/night

    Maui Kai 108

    Maui Kai 108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $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
  19. $186 to $336/night

    Villas of Kamalii 37

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $148 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $179 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $426 to $533/night

    Wailea Ekolu 1606

    Wailea Ekolu 1606

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $124 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $204 to $370/night

    Honua Kai 322

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $249 to $588/night

    Sands of Kahana 316

    Sands of Kahana 316

    2 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $192 to $238/night

    Kamahana 24

    Kamahana 24

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  27. $260/night

    Turtle Bay Takanoha**NUC 90-TVU-0557

    Turtle Bay Takanoha**NUC 90-TVU-0557

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $223 to $420/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $299 to $351/night

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. $329/night

    Turtle Bay Hanalei***TA-147868876801 Available 30 night rental

    Turtle Bay Hanalei***TA-147868876801 Available 30 night ...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $236/night

    Turtle Bay Red Ginger***TA-068313907201 Available 30 day rental

    Turtle Bay Red Ginger***TA-068313907201 Available 30 day...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $345/night

    Turtle Bay Sugar Cane***Available 30 day rental

    Turtle Bay Sugar Cane***Available 30 day rental

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $191/night

    Turtle Bay Sea Shells**TA-154567065601 Available 30 nights

    Turtle Bay Sea Shells**TA-154567065601 Available 30 nigh...

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $241/night

    Turtle Bay Pikake**TA-010173030401 Available 30 night rental

    Turtle Bay Pikake**TA-010173030401 Available 30 night re...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $161/night

    Turtle Bay Guava**TA-009966796801 Available 30 nights

    Turtle Bay Guava**TA-009966796801 Available 30 nights

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $271/night

    Turtle Bay Morning Glory***TA-147878707201 Available 30 nights

    Turtle Bay Morning Glory***TA-147878707201 Available 30 ...

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $351/night

    Turtle Bay White Ginger***TA-068313907201 Available 30 days

    Turtle Bay White Ginger***TA-068313907201 Available 30 d...

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $202/night

    Turtle Bay Primrose***TA-016722124801 Available 30 nights

    Turtle Bay Primrose***TA-016722124801 Available 30 night...

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $248/night

    Turtle Bay Blue Hawaii***NUC 90-TVU-0192

    Turtle Bay Blue Hawaii***NUC 90-TVU-0192

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. $191/night

    Turtle Bay Pineapple Delight**TA088724684801 Availalbe 30 days

    Turtle Bay Pineapple Delight**TA088724684801 Availalbe 3...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $237/night

    Turtle Bay Honu Lani***TA-006757785601 Available 30 nights

    Turtle Bay Honu Lani***TA-006757785601 Available 30 nigh...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $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
  43. $156/night

    Turtle Bay Hula House Budget NUC 90-TVU-0566

    Turtle Bay Hula House Budget NUC 90-TVU-0566

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $215 to $257/night

    Sealodge F9

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  45. $198 to $355/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $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
  47. $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
  48. $261 to $473/night

    Kaanapali Royal B303

    Kaanapali Royal B303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $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
  50. $219 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  51. $1,109/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
  52. $574 to $1,347/night

    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  53. $203 to $553/night

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $188 to $444/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $144 to $318/night

    Kaleialoha 202

    Kaleialoha 202

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. $358/night

    Turtle Bay Pupukea***NUC 90-TVU-0246

    Turtle Bay Pupukea***NUC 90-TVU-0246

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $163 to $313/night

    Kona Makai 2-102

    Kona Makai 2-102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $426 to $619/night

    Ilikai #1743

    Ilikai #1743

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  59. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. $260/night

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    1 BedroomBathroomsSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $199 to $239/night

    Aina Nalu K 205

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $362 to $421/night

    Kona Makai 3-302

    Kona Makai 3-302

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $204 to $238/night

    Cliffs 7303

    Cliffs 7303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $135 to $411/night

    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $516 to $620/night

    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $151 to $263/night

    Kahana Reef 303

    Kahana Reef 303

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $163 to $274/night

    Kaanapali Shores 628

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $224 to $443/night

    Kaanapali Royal E101

    Kaanapali Royal E101

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $197 to $350/night

    Kona Magic Sands 313

    Kona Magic Sands 313

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $279 to $337/night

    Casa De Emdeko 211

    Casa De Emdeko 211

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $156/night

    Turtle Bay 126 West Budget NUC 90-TVU-0538

    Turtle Bay 126 West Budget NUC 90-TVU-0538

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $205 to $358/night

    Aina Nalu A 201

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $224 to $449/night

    Puamana 15-3

    Puamana 15-3

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $186 to $338/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $249 to $446/night

    Kahana Sunset E4

    Kahana Sunset E4

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $203 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $210 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $227 to $280/night

    Sealodge G8

    Sealodge G8

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  83. $223 to $260/night

    Keauhou Akahi 210

    Keauhou Akahi 210

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  84. $623 to $748/night

    Hale Kalani

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  85. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $195 to $326/night

    Kona Isle D4

    Kona Isle D4

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  87. $401 to $699/night

    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  88. $313 to $741/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $171 to $448/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. $210 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $178 to $487/night

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. $263 to $413/night

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  93. $118 to $261/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $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
  95. $276 to $332/night

    Kahana Sunset D2

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  96. $208 to $253/night

    Sands Of Kahana 231

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  97. $197 to $248/night

    Ridge Villa 1422

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  98. $214 to $270/night

    Bay Villa 33B2

    Bay Villa 33B2

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  99. $253 to $309/night

    Kahana Sunset D10

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  100. $428 to $484/night

    Kahana Sunset F4

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool