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. $329/night

    Turtle Bay Wicked Wahine***TA-129213644801

    Turtle Bay Wicked Wahine***TA-129213644801

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $283/night

    Turtle Bay Bird of Paradise**TA-086947840001

    Turtle Bay Bird of Paradise**TA-086947840001

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  3. $260 to $271/night

    Turtle Bay NorthShore Haven***TA074664550401

    Turtle Bay NorthShore Haven***TA074664550401

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $149 to $237/night

    Naupaka- Kahuku Condo

    Naupaka- Kahuku Condo

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  5. $161/night

    Turtle Bay 19th Hole*TA-017785446401

    Turtle Bay 19th Hole*TA-017785446401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $254/night

    Turtle Bay Paniolo**TA-202779033601

    Turtle Bay Paniolo**TA-202779033601

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  7. $241/night

    Turtle Bay The Darrolee**TA-151924326401

    Turtle Bay The Darrolee**TA-151924326401

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $248/night

    Crown Flower Turtle Bay Condo

    Crown Flower Turtle Bay Condo

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  9. $237/night

    Turtle Bay Pakalana***TA-147815833601

    Turtle Bay Pakalana***TA-147815833601

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $260 to $271/night

    Turtle Bay Sunset Retreat***TA-188332646401

    Turtle Bay Sunset Retreat***TA-188332646401

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $202 to $225/night

    Turtle Bay On The Green**TA-124574924801

    Turtle Bay On The Green**TA-124574924801

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $146 to $158/night

    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  14. $304 to $467/night

    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    FREE CANCELLATION
  15. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  16. $428 to $484/night

    Kahana Sunset A5

    Kahana Sunset A5

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  17. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  18. $276 to $332/night

    Kahana Sunset E8

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  19. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  20. $276 to $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  21. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  22. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  23. $248 to $304/night

    Bay Villa 30G1

    Bay Villa 30G1

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool
  24. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  25. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  26. $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
  27. $146 to $262/night

    Ilikai 1130

    Ilikai 1130

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $260 to $311/night

    Kamaole Sands #09-102

    Kamaole Sands #09-102

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $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
  30. $563 to $781/night

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  31. $183 to $314/night

    Papakea E306

    Papakea E306

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  32. $297 to $390/night

    Maui Kamaole #b-107

    Maui Kamaole #b-107

    1 BedroomBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $239 to $296/night

    Kauhale Makai #122

    Kauhale Makai #122

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $781 to $1,219/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  35. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  36. $253 to $309/night

    Kahana Sunset B1

    Kahana Sunset B1

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  37. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  38. $235 to $296/night

    Kihei Akahi #C-317

    Kihei Akahi #C-317

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  39. $371 to $458/night

    Kamaole Sands #03-407

    Kamaole Sands #03-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $397 to $977/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  41. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  42. $392 to $523/night

    Plantation Cottage

    Plantation Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  43. $235 to $296/night

    Kihei Akahi #C-109

    Kihei Akahi #C-109

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  44. $393 to $480/night

    Kamaole Sands #10-407

    Kamaole Sands #10-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $235 to $296/night

    Kihei Akahi #C-608

    Kihei Akahi #C-608

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  46. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  47. $466 to $1,209/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. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  49. $305 to $390/night

    Kauhale Makai #132

    Kauhale Makai #132

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $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
  51. $344 to $460/night

    Kihei Surfside #210

    Kihei Surfside #210

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  52. $253 to $301/night

    Cliffs 8205

    Cliffs 8205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  53. $241 to $301/night

    Cliffs 4206

    Cliffs 4206

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  54. $219 to $280/night

    OTA House

    OTA House

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  55. $253 to $311/night

    Kauhale Makai #605

    Kauhale Makai #605

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $370 to $466/night

    Maui Banyan #G-209

    Maui Banyan #G-209

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $371 to $458/night

    Kamaole Sands #06-405

    Kamaole Sands #06-405

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $493 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $481 to $856/night

    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua Ridge Villa 1214 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  60. $326 to $383/night

    Kahana Sunset A3

    Kahana Sunset A3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  61. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $978 to $1,166/night

    Punahele Point

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
  63. $282 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  64. $282 to $346/night

    Nihilani 22C

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool
  65. $334 to $556/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  66. $239 to $362/night

    Plantations at Princeville #1212

    Plantations at Princeville #1212

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  67. $456 to $652/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  68. $1,303 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  69. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  70. $340 to $503/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  71. $241 to $279/night

    Maui Vista #1322

    Maui Vista #1322

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  72. $241 to $279/night

    Maui Vista #3202

    Maui Vista #3202

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  73. $781 to $1,219/night

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  74. $168 to $258/night

    Waikiki Banyan Tower 2 Suite 2904- STQP

    Waikiki Banyan Tower 2 Suite 2904- STQP

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $313 to $526/night

    MAALAEA SURF, #C-8

    MAALAEA SURF, #C-8

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  76. $931 to $1,459/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  77. $448 to $1,065/night

    WAILEA ELUA, #0902

    WAILEA ELUA, #0902

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  78. $813 to $1,219/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  79. $243 to $423/night

    Aina Nalu B204

    Aina Nalu B204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $212 to $333/night

    Pohailani Maui 115

    Pohailani Maui 115

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  81. $271 to $461/night

    Kapalua Golf Villa 14T

    Kapalua Golf Villa 14T

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  82. $201 to $502/night

    Kaleialoha #207

    Kaleialoha #207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $195 to $502/night

    Kaleialoha #315

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  85. $172 to $275/night

    Ilikai 1904

    Ilikai 1904

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $281 to $297/night

    Casa De Emdeko 111

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  87. $263 to $492/night

    Kona Makai 1-204

    Kona Makai 1-204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $326 to $342/night

    Keauhou Kona Surf & Racquet Club 2103

    Keauhou Kona Surf & Racquet Club 2103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  89. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  90. $326 to $342/night

    Keauhou Kona Surf & Racquet Club #176

    Keauhou Kona Surf & Racquet Club #176

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  91. $349 to $395/night

    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $263 to $382/night

    Keauhou Kona Surf & Racquet Townhouse #36

    Keauhou Kona Surf & Racquet Townhouse #36

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  93. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  94. $282 to $546/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  95. $362 to $512/night

    Puu Poa 107

    Puu Poa 107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  96. $392 to $542/night

    Puu Poa 310

    Puu Poa 310

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  97. $222 to $228/night

    Keauhou Kona Surf & Racquet Club#37

    Keauhou Kona Surf & Racquet Club#37

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  98. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $132 to $304/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $230 to $496/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

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