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. $306/night

    Turtle Bay Haupia**TA-136982118401

    Turtle Bay Haupia**TA-136982118401

    2 BedroomsBathroomsSleeps 8
    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. $237/night

    Turtle Bay Pakalana***TA-147815833601

    Turtle Bay Pakalana***TA-147815833601

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $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
  9. $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
  10. $190 to $731/night

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  11. $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
  12. $140/night

    Bamboo 906 Condominium

    Bamboo 906 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  13. $142 to $197/night

    Bamboo 1001 Condominium

    Bamboo 1001 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $145 to $180/night

    Diamond Head Beach Hotel 1104

    Diamond Head Beach Hotel 1104

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  15. $153 to $219/night

    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  16. $141 to $163/night

    Kuhio Village 1205 Condominium

    Kuhio Village 1205 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  17. $158 to $203/night

    Tradewinds Plaza 304

    Tradewinds Plaza 304

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  18. $124 to $179/night

    Hawaiian King 405 Apartment

    Hawaiian King 405 Apartment

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $140 to $186/night

    Palms Waikiki 815 Hotel Suites

    Palms Waikiki 815 Hotel Suites

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $133 to $169/night

    Waikiki Grand 312 Condo

    Waikiki Grand 312 Condo

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $142 to $179/night

    Waikiki Grand 408 Studio

    Waikiki Grand 408 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. $124 to $174/night

    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $122/night

    Waikiki Grand 605 Condo

    Waikiki Grand 605 Condo

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  24. $144 to $186/night

    Waikiki Grand 811 Studio

    Waikiki Grand 811 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  25. $107 to $158/night

    Waikiki Grand 216 Hotel

    Waikiki Grand 216 Hotel

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $248 to $309/night

    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $142 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  29. $371 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $167 to $197/night

    Waikiki Grand 908 Studio

    Waikiki Grand 908 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $123 to $596/night

    Waikiki Grand Condominium 922 *Legal Vacation Rental

    Waikiki Grand Condominium 922 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $344 to $488/night

    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  33. $110 to $203/night

    Discovery Bay 2502

    Discovery Bay 2502

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  34. $392 to $523/night

    Plantation Cottage

    Plantation Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  35. $237 to $502/night

    Maui Eldorado Condo C102

    Maui Eldorado Condo C102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  37. $238 to $423/night

    Aina Nalu B204

    Aina Nalu B204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $133 to $203/night

    Waikiki Grand 315 Studio

    Waikiki Grand 315 Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $207 to $496/night

    Maui Eldorado Condo K217

    Maui Eldorado Condo K217

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $358 to $816/night

    Maui Eldorado Condo J100

    Maui Eldorado Condo J100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $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
  42. $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
  43. $176 to $502/night

    Kaleialoha #115

    Kaleialoha #115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $174 to $211/night

    Maui Sands K1

    Maui Sands K1

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  45. $599 to $1,616/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  46. $601 to $1,317/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  47. $363 to $869/night

    Pili Mai 3G

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  48. $304 to $750/night

    Kanaloa 701

    Kanaloa 701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  49. $1,764 to $6,409/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  50. $280 to $682/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  51. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  52. $292 to $706/night

    Sea Village 4107

    Sea Village 4107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  53. $899 to $2,678/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  54. $542 to $1,328/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  55. $1,209 to $4,266/night

    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  56. $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
  57. $375 to $720/night

    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  58. $238 to $543/night

    Kona Pacific B310

    Kona Pacific B310

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
  59. $482 to $720/night

    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  60. $256 to $543/night

    Keauhou Resort 104

    Keauhou Resort 104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  61. $776 to $2,611/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  62. $252 to $672/night

    Waikoloa Villas F-100

    Waikoloa Villas F-100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  63. $262 to $647/night

    Kona Makai 6305

    Kona Makai 6305

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
  64. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  65. $500 to $1,333/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  66. $1,063 to $4,047/night

    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  67. $780 to $1,611/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  68. $254 to $621/night

    Paki Maui 313

    Paki Maui 313

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  69. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  70. $238 to $598/night

    Palm Leaf

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  71. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  72. $157 to $242/night

    Surf & Racquet Club 6201

    Surf & Racquet Club 6201

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $688 to $1,623/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  75. $204 to $238/night

    Mauna Kai 5A

    Mauna Kai 5A

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  76. $227 to $293/night

    Alii Kai 3103

    Alii Kai 3103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  77. $156 to $274/night

    Hale Ono Loa 401

    Hale Ono Loa 401

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $188 to $438/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  79. $188 to $415/night

    Honua Kai 1024

    Honua Kai 1024

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $124 to $319/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $211 to $324/night

    Napili Shores E243

    Napili Shores E243

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $181 to $464/night

    Eldorado G205

    Eldorado G205

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $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
  84. $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
  85. $195 to $299/night

    Napili Shores E240

    Napili Shores E240

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $193 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $200 to $438/night

    Lauloa 105

    Lauloa 105

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $181 to $331/night

    Hale Ono Loa 106

    Hale Ono Loa 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $120 to $294/night

    Kaleialoha 402

    Kaleialoha 402

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $220 to $501/night

    Maui Eldorado Condo J120

    Maui Eldorado Condo J120

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  91. $207 to $501/night

    Maui Eldorado Condo K206

    Maui Eldorado Condo K206

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  93. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  94. $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
  95. $233 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $245 to $363/night

    Poipu Kapili 46

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  97. $227 to $285/night

    Sealodge J1

    Sealodge J1

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  98. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  99. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  100. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION