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. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  2. $217 to $604/night

    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  3. $135 to $169/night

    Kepuhi Beach Resort 2143

    Kepuhi Beach Resort 2143

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $124 to $169/night

    Wavecrest A109

    Wavecrest A109

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  5. $327 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $371 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $180 to $609/night

    Aina Nalu Premier Platinum Condo H206

    Aina Nalu Premier Platinum Condo H206

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  8. $153 to $219/night

    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  9. $178 to $248/night

    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  10. $113 to $152/night

    Wavecrest B309

    Wavecrest B309

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  11. $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
  12. $181 to $636/night

    Napili Shores F147

    Napili Shores F147

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  13. $247 to $291/night

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  14. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  15. $223 to $306/night

    Hale Mala Hina-245

    Hale Mala Hina-245

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $288 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $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
  18. $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
  19. $279 to $401/night

    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  20. $257 to $363/night

    Poipu Kapili 46

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  21. $282 to $484/night

    Honua Kai 506

    Honua Kai 506

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $311 to $365/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $231 to $269/night

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  24. $1,797 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  25. $219 to $280/night

    OTA House

    OTA House

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  26. $306 to $358/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  29. $235 to $296/night

    Kihei Akahi #C-109

    Kihei Akahi #C-109

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  30. $204 to $353/night

    Kihei Akahi Resort- Unit C405

    Kihei Akahi Resort- Unit C405

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  31. $270 to $346/night

    Pali Ke Kua #204

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  32. $1,303 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  33. $688 to $1,464/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  34. $362 to $422/night

    Pali Ke Kua 203

    Pali Ke Kua 203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $241 to $283/night

    Pali Ke Kua 10

    Pali Ke Kua 10

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $235 to $301/night

    Sealodge E4

    Sealodge E4

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  38. $790 to $1,051/night

    Hale Ola Kai

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  39. $264 to $271/night

    New Listing! Hawaiian Experience- Walk to Two Step

    New Listing! Hawaiian Experience- Walk to Two Step

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  40. $238 to $275/night

    Sealodge D1

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  41. $201 to $324/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  42. $361 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  43. $978 to $1,129/night

    Punahele Point

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
  44. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  45. $456 to $616/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  46. $158 to $350/night

    Kona Pacific B511

    Kona Pacific B511

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  47. $157 to $242/night

    Sea Village 3-212

    Sea Village 3-212

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $121 to $156/night

    Sandpiper 121B

    Sandpiper 121B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $363 to $985/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
  50. $392 to $542/night

    Puu Poa 310

    Puu Poa 310

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $235 to $301/night

    Cliffs 4205

    Cliffs 4205

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $241 to $271/night

    Plantation 1111

    Plantation 1111

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $241 to $301/night

    Cliffs 4206

    Cliffs 4206

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $164 to $502/night

    Kaleialoha #315

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $224 to $458/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $438 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $379 to $485/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $117 to $243/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $191 to $536/night

    Kona Bali Kai #206- 2 Bedroom

    Kona Bali Kai #206- 2 Bedroom

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $261 to $734/night

    Royal Sea Cliff #418

    Royal Sea Cliff #418

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $184 to $535/night

    Vista Waikoloa C305

    Vista Waikoloa C305

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $253 to $734/night

    Kona Reef #D31

    Kona Reef #D31

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $138 to $438/night

    THE SHORES OF MAUI #223

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $149 to $450/night

    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $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
  67. $690 to $1,616/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  68. $304 to $652/night

    Kanaloa 701

    Kanaloa 701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  69. $780 to $1,395/night

    Hale Poola

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  70. $500 to $1,095/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  71. $481 to $899/night

    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  72. $482 to $1,220/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  73. $292 to $616/night

    Sea Village 4107

    Sea Village 4107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  74. $899 to $2,407/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  75. $631 to $1,335/night

    Koa Kai Hale

    Koa Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  76. $1,434 to $3,932/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  77. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  78. $1,160 to $3,737/night

    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  79. $1,131 to $3,225/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
  80. $375 to $720/night

    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  81. $1,063 to $3,442/night

    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  82. $766 to $2,122/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  83. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  84. $174 to $324/night

    Sealodge J3

    Sealodge J3

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $151 to $423/night

    Keauhou Punahele #B202

    Keauhou Punahele #B202

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $171 to $480/night

    Country Club Villas #208

    Country Club Villas #208

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $120 to $411/night

    Waikiki Gem at the Hawaiian King

    Waikiki Gem at the Hawaiian King

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $625 to $1,648/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $169 to $225/night

    Ke Nani Kai 218

    Ke Nani Kai 218

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. $152 to $197/night

    Ke Nani Kai 237

    Ke Nani Kai 237

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  91. $113 to $135/night

    Kepuhi Beach 1226

    Kepuhi Beach 1226

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $322 to $435/night

    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $250 to $741/night

    Pohailani 231

    Pohailani 231

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $309 to $438/night

    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  96. $485 to $652/night

    Hale Ulu'wehi

    Hale Ulu'wehi

    4 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  97. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  98. $167 to $248/night

    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $225 to $281/night

    A Ala Hale

    A Ala Hale

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  100. $284 to $747/night

    Hale Ono Loa 120

    Hale Ono Loa 120

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION