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. $217 to $604/night

    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  2. $140/night

    Bamboo 906 Condominium

    Bamboo 906 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  3. $178 to $248/night

    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  4. $360 to $557/night

    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  5. $153 to $219/night

    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  6. $158 to $203/night

    Tradewinds Plaza 304

    Tradewinds Plaza 304

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  7. $129 to $169/night

    Waikiki Grand 312 Condo

    Waikiki Grand 312 Condo

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $124 to $179/night

    Waikiki Grand 315 Studio

    Waikiki Grand 315 Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  9. $142 to $179/night

    Waikiki Grand 408 Studio

    Waikiki Grand 408 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $124 to $174/night

    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $128/night

    Waikiki Grand 600 Condo

    Waikiki Grand 600 Condo

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $122/night

    Waikiki Grand 605 Condo

    Waikiki Grand 605 Condo

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  13. $144/night

    Waikiki Grand 704 Condo

    Waikiki Grand 704 Condo

    Studio BathroomSleeps 2
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  14. $167 to $197/night

    Waikiki Grand 908 Studio

    Waikiki Grand 908 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $100 to $158/night

    Waikiki Grand 216 Hotel

    Waikiki Grand 216 Hotel

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $124 to $179/night

    Hawaiian King 405 Apartment

    Hawaiian King 405 Apartment

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $142 to $197/night

    Bamboo 1001 Condominium

    Bamboo 1001 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $141 to $163/night

    Kuhio Village 1205 Condominium

    Kuhio Village 1205 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  20. $133 to $213/night

    Marine Surf 1708 Studio

    Marine Surf 1708 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $242 to $309/night

    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. $174 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
  23. $202 to $636/night

    Napili Shores F147

    Napili Shores F147

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  24. $364 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $283 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $144 to $186/night

    Waikiki Grand 811 Studio

    Waikiki Grand 811 Studio

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  27. $134 to $186/night

    Palms Waikiki 815 Hotel Suites

    Palms Waikiki 815 Hotel Suites

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $99 to $129/night

    Aloha Surf 207

    Aloha Surf 207

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $144/night

    Art Cottage

    Art Cottage

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. $191/night

    Hale Kipa

    Hale Kipa

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $329/night

    Turtle Bay Wicked Wahine***TA-129213644801

    Turtle Bay Wicked Wahine***TA-129213644801

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $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
  33. $260 to $271/night

    Turtle Bay NorthShore Haven***TA074664550401

    Turtle Bay NorthShore Haven***TA074664550401

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $149 to $237/night

    Naupaka- Kahuku Condo

    Naupaka- Kahuku Condo

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $161/night

    Turtle Bay 19th Hole*TA-017785446401

    Turtle Bay 19th Hole*TA-017785446401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $306/night

    Turtle Bay Haupia**TA-136982118401

    Turtle Bay Haupia**TA-136982118401

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $254/night

    Turtle Bay Paniolo**TA-202779033601

    Turtle Bay Paniolo**TA-202779033601

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. $241/night

    Turtle Bay The Darrolee**TA-151924326401

    Turtle Bay The Darrolee**TA-151924326401

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $248/night

    Crown Flower Turtle Bay Condo

    Crown Flower Turtle Bay Condo

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $237/night

    Turtle Bay Pakalana***TA-147815833601

    Turtle Bay Pakalana***TA-147815833601

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $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
  42. $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
  43. $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
  44. $152 to $219/night

    Nani Kai Hale # 307

    Nani Kai Hale # 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  45. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  46. $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
  47. $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
  48. $246 to $476/night

    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $196 to $342/night

    Maui Kamaole #J-103

    Maui Kamaole #J-103

    1 BedroomBathroomsSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $162 to $299/night

    Keauhou Punahele E-102

    Keauhou Punahele E-102

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  51. $525 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $538 to $860/night

    Papakea K-402

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $243 to $441/night

    Royal Kahana 1012

    Royal Kahana 1012

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  54. $243 to $333/night

    Pohailani Maui 115

    Pohailani Maui 115

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  55. $211 to $339/night

    Maui Kamaole #M-105

    Maui Kamaole #M-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $289 to $620/night

    HOL 119

    HOL 119

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $370 to $741/night

    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $172 to $275/night

    Ilikai 1904

    Ilikai 1904

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $556 to $1,063/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  60. $219 to $391/night

    Maui Kamaole #G-107

    Maui Kamaole #G-107

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $317 to $565/night

    Maui Kamaole #A-201

    Maui Kamaole #A-201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $254 to $452/night

    Grand Champions #45

    Grand Champions #45

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $184 to $318/night

    Pacific Shores B406

    Pacific Shores B406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  65. $350 to $467/night

    Sea Village 4-205

    Sea Village 4-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $173 to $289/night

    Maui Vista #2-320

    Maui Vista #2-320

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  67. $195 to $502/night

    Kaleialoha #214

    Kaleialoha #214

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $282 to $528/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  69. $217 to $333/night

    Royal Kahana 702

    Royal Kahana 702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. $126 to $231/night

    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $138 to $277/night

    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $138 to $277/night

    Kihei Bay Surf #109

    Kihei Bay Surf #109

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $302 to $517/night

    Kamaole Sands #7-403

    Kamaole Sands #7-403

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $174 to $211/night

    Maui Sands K1

    Maui Sands K1

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  75. $141 to $262/night

    Ilikai 1236

    Ilikai 1236

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $585 to $622/night

    Kona Makai 1-301

    Kona Makai 1-301

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $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
  78. $309 to $326/night

    Casa De Emdeko 111

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  79. $174 to $375/night

    Kaleialoha 211

    Kaleialoha 211

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. $361 to $749/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  81. $269 to $594/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. $175 to $349/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $206 to $498/night

    Wailea Ekahi 49A

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $161 to $448/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $139 to $456/night

    Hale Ono Loa 102

    Hale Ono Loa 102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $249 to $526/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  88. $211 to $543/night

    International Colony Club 20

    International Colony Club 20

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $148 to $353/night

    Kihei Akahi Resort- Unit C405

    Kihei Akahi Resort- Unit C405

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  90. $251 to $495/night

    Kanai A Nalu 318

    Kanai A Nalu 318

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  91. $389 to $428/night

    Keauhou Kona Surf & Racket Club Townhouse #4

    Keauhou Kona Surf & Racket Club Townhouse #4

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $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
  93. $110 to $321/night

    Ilikai Marina 1783

    Ilikai Marina 1783

    1 Bedroom BathroomSleeps 3
    1 night minstay
    FREE CANCELLATION
  94. $133 to $390/night

    Ilikai Tower 827

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  95. $157 to $430/night

    Ilikai Tower 633

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  96. $145 to $361/night

    Ilikai Tower 333

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  97. $128 to $353/night

    Ilikai Tower 611

    Ilikai Tower 611

    1 Bedroom BathroomSleeps 3
    1 night minstay
    Pool
    FREE CANCELLATION
  98. $145 to $368/night

    Ilikai Tower 735

    Ilikai Tower 420

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  99. $150 to $484/night

    Ilikai Tower 2136

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  100. $154 to $455/night

    Ilikai Tower 814

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION