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. $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
  2. $146 to $286/night

    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    2 BedroomsBathroomsSleeps 6
    4 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. $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
  5. $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
  6. $155 to $269/night

    Kamaole Sands 8-203

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $274 to $409/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $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
  9. $200 to $436/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $206 to $406/night

    Aina Nalu I104

    Aina Nalu I104

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $276 to $370/night

    Honua Kai 322

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $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
  13. $249 to $312/night

    Malolo Cottage

    Malolo Cottage

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  14. $203 to $527/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
  15. $205 to $358/night

    Aina Nalu A 201

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $516 to $620/night

    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $214 to $238/night

    Cliffs 7303

    Cliffs 7303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $199 to $239/night

    Aina Nalu K 205

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $174 to $421/night

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $454 to $699/night

    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  23. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $300 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $198 to $323/night

    Maui Kai 108

    Maui Kai 108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $219 to $438/night

    Maui Kai 206

    Maui Kai 206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $250 to $350/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $253 to $313/night

    Keawakapu 208

    Keawakapu 208

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  29. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $201 to $251/night

    Hale Kamaole 109

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $144 to $219/night

    Island Surf 306

    Island Surf 306

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $290 to $435/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $220 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $260 to $394/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $311 to $738/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $293 to $361/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $344 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $426 to $531/night

    Wailea Ekolu 1606

    Wailea Ekolu 1606

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $174 to $299/night

    Eldorado J111

    Eldorado J111

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  44. $231 to $449/night

    Puamana 24-3

    Puamana 24-3

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  45. $2,000 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  47. $249 to $312/night

    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  48. $216 to $235/night

    Lil Grass Shack-103

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  49. $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
  50. $208 to $731/night

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $361 to $479/night

    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    4 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  52. $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
  53. $196 to $369/night

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $239 to $263/night

    PentHouse 701

    PentHouse 701

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $188 to $435/night

    Aina Nalu A104

    Aina Nalu A104

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $186 to $324/night

    Kihei Akahi C-616

    Kihei Akahi C-616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $186 to $366/night

    Eldorado A203

    Eldorado A203

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $372 to $444/night

    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $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
  60. $264 to $299/night

    Hula Hideaway-303

    Hula Hideaway-303

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $229 to $365/night

    Honua Kai Konea 224

    Honua Kai Konea 224

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $282 to $477/night

    Honua Kai Konea 508

    Honua Kai Konea 508

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $306 to $394/night

    Kahana Sunset C 3

    Kahana Sunset C 3

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $278 to $341/night

    Junior Suite Oceanfront #702

    Junior Suite Oceanfront #702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $278 to $341/night

    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $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
  67. $280 to $374/night

    Nihilani 28C

    Nihilani 28C

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $748 to $1,060/night

    Malapua

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  69. $249 to $312/night

    Chung Cottage

    Chung Cottage

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  70. $686 to $936/night

    Hale A Kai

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  71. $717 to $904/night

    Hale Koaniani

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  72. $181 to $249/night

    Hale Moi #216A

    Hale Moi #216A

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  73. $1,870 to $2,494/night

    Wilikoki House

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  74. $408 to $803/night

    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  75. $249 to $274/night

    Nohonani

    Nohonani

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    FREE CANCELLATION
  76. $275 to $353/night

    Honua Kai 210

    Honua Kai 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $397 to $1,093/night

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    2 BedroomsBathroomsSleeps 4
    6 nights minstay
    Pool Hot Tub
  78. $408 to $1,383/night

    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  79. $278 to $341/night

    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $341 to $413/night

    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $244 to $328/night

    Aina Nalu G204

    Aina Nalu G204

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $235 to $371/night

    Aina Nalu C 203

    Aina Nalu C 203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $220 to $448/night

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $159 to $356/night

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $137 to $258/night

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  86. $135 to $344/night

    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  87. $439 to $715/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $278 to $400/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $510 to $573/night

    Kaanapali Shores 725

    Kaanapali Shores 725

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $266 to $486/night

    Maui Vista 1417

    Maui Vista 1417

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  91. $219 to $344/night

    Pacific Shores B414

    Pacific Shores B414

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $280 to $323/night

    Eldorado K104

    Eldorado K104

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $201 to $315/night

    Island Surf 409

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. $269 to $369/night

    Eldorado K102

    Eldorado K102

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $418 to $659/night

    Kaanapali Shores 527

    Kaanapali Shores 527

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $260 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $246 to $374/night

    Kahana Reef 201

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $240 to $286/night

    Maalaea Banyans 203

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $306 to $556/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $329 to $490/night

    Island Sands 210

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION