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. $161/night

    Turtle Bay 19th Hole*TA-017785446401

    Turtle Bay 19th Hole*TA-017785446401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  5. $254/night

    Turtle Bay Paniolo**TA-202779033601

    Turtle Bay Paniolo**TA-202779033601

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  6. $237/night

    Turtle Bay Pakalana***TA-147815833601

    Turtle Bay Pakalana***TA-147815833601

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $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
  8. $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
  9. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  10. $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
  11. $153 to $219/night

    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  12. $124 to $179/night

    Hawaiian King 405 Apartment

    Hawaiian King 405 Apartment

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $140 to $213/night

    Condo with Ocean View! On Golf Course, Minutes from Beaches!

    Condo with Ocean View! On Golf Course, Minutes from Beac...

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  15. $213 to $298/night

    Ocean & Golf Course Views! 3 Bedroom- Waikoloa Villas A202

    Ocean & Golf Course Views! 3 Bedroom- Waikoloa Villa...

    3 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool
    FREE CANCELLATION
  16. $142 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  17. $392 to $523/night

    Plantation Cottage

    Plantation Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  18. $374 to $499/night

    Hanalei Colony G1

    Hanalei Colony G1

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  19. $260 to $437/night

    Puu Poa #305

    Puu Poa #305

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  20. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  21. $287 to $350/night

    Keauhou Kona Surf & Racquet Club #176

    Keauhou Kona Surf & Racquet Club #176

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $350/night

    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  23. $467 to $585/night

    Kona Makai 1-301

    Kona Makai 1-301

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $287 to $350/night

    Keauhou Kona Surf & Racquet Club 2103

    Keauhou Kona Surf & Racquet Club 2103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  25. $262 to $547/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  26. $363 to $869/night

    Pili Mai 3G

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  27. $280 to $682/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  28. $292 to $706/night

    Sea Village 4107

    Sea Village 4107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  29. $899 to $2,678/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  30. $542 to $1,328/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  31. $1,081 to $3,790/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  32. $776 to $2,611/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  33. $252 to $672/night

    Waikoloa Villas F-100

    Waikoloa Villas F-100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  34. $262 to $647/night

    Kona Makai 6305

    Kona Makai 6305

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
  35. $411 to $1,096/night

    Kona Makai 6301

    Kona Makai 6301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  36. $780 to $1,611/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  37. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  38. $363 to $986/night

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $198 to $579/night

    Kanaloa At Kona #3001

    Kanaloa At Kona #3001

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $144 to $375/night

    White Sands Village #135

    White Sands Village #135

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $250 to $734/night

    Royal Sea Cliff #418

    Royal Sea Cliff #418

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $219 to $649/night

    Kanaloa At Kona #3701

    Kanaloa At Kona #3701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $163 to $480/night

    Country Club Villas #208

    Country Club Villas #208

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $149 to $453/night

    White Sands Village #206

    White Sands Village #206

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $300 to $480/night

    White Sands Village #201

    White Sands Village #201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $343 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
  47. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  49. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  51. $688 to $1,623/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  52. $227 to $293/night

    Alii Kai 3103

    Alii Kai 3103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  53. $188 to $438/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. $181 to $464/night

    Eldorado G205

    Eldorado G205

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $250 to $292/night

    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. $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
  57. $336 to $606/night

    Mahana Resort #304

    Mahana Resort #304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $120 to $294/night

    Kaleialoha 402

    Kaleialoha 402

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $231 to $456/night

    Hale Ono Loa 102

    Hale Ono Loa 102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $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
  61. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  62. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  63. $324 to $669/night

    Mahana Resort #706

    Mahana Resort #706

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $319 to $574/night

    Mahana Resort #804

    Mahana Resort #804

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $290 to $534/night

    Papakea #G106

    Papakea #G106

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $294 to $494/night

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  67. $233 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $246 to $509/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $278 to $600/night

    Kaanapali Royal #A303

    Kaanapali Royal #A303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $412 to $940/night

    Papakea #C403

    Papakea #C403

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $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
  72. $245 to $363/night

    Poipu Kapili 46

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  74. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  75. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  76. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  77. $173 to $279/night

    Kahana Villa F410

    Kahana Villa F410

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  80. $470 to $953/night

    WAILEA ELUA, #0801*

    WAILEA ELUA, #0801*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  81. $469 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $391 to $654/night

    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $233 to $345/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $149 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $288 to $494/night

    Kapalua Bay Villa 12G5 Ocean View

    Kapalua Bay Villa 12G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  86. $342 to $669/night

    Mahana Resort #616

    Mahana Resort #616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $275 to $413/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  89. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $291 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  91. $188 to $258/night

    164

    164

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $186 to $459/night

    Papakea #A105

    Papakea #A105

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  93. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $203 to $383/night

    Papakea #C108

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $235 to $469/night

    Wailea Ekahi 50C

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $456 to $883/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  98. $163 to $239/night

    Hale Pineapple

    Hale Pineapple

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  99. $392 to $542/night

    Puu Poa 310

    Puu Poa 310

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $219 to $596/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION