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. $144/night

    Bamboo 801 Condominium

    Bamboo 801 Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  2. $160 to $197/night

    Diamond Head Beach Hotel 1105

    Diamond Head Beach Hotel 1105

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  3. $248 to $326/night

    Diamond Head Beach Hotel 1202

    Diamond Head Beach Hotel 1202

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  4. $309 to $438/night

    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  5. $179 to $270/night

    Diamond Head Beach Hotel 802

    Diamond Head Beach Hotel 802

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  6. $126/night

    Kuhio Village 1103 Condominium

    Kuhio Village 1103 Condominium

    Studio BathroomSleeps 3
    3 nights minstay
    FREE CANCELLATION
  7. $142 to $197/night

    Palms Waikiki 220 Studio

    Palms Waikiki 220 Studio

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  8. $129 to $174/night

    Waikiki Grand 412 Condo

    Waikiki Grand 412 Condo

    Studio BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  9. $134/night

    Waikiki Grand 500 Condo

    Waikiki Grand 500 Condo

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $155/night

    Pacific Monarch 3101 Condo

    Pacific Monarch 3101 Condo

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $152 to $248/night

    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $217 to $623/night

    Aina Nalu C108

    Aina Nalu C108

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $217 to $623/night

    Aina Nalu C102

    Aina Nalu C102

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $144 to $190/night

    Waikiki Grand 715 Condo

    Waikiki Grand 715 Condo

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  15. $96 to $359/night

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $151/night

    Bamboo 902 Hotel Suites

    Bamboo 902 Hotel Suites

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $140/night

    Waikiki Grand 701 Studio

    Waikiki Grand 701 Studio

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  18. $144 to $186/night

    Diamond Head Beach Hotel 1005

    Diamond Head Beach Hotel 1005

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  19. $106 to $158/night

    Aloha Surf 1507 Condominium

    Aloha Surf 1507 Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $124/night

    Aloha Surf 610 Apartment

    Aloha Surf 610 Apartment

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  21. $156/night

    Bamboo 610 Studio Apartment

    Bamboo 610 Studio Apartment

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $108/night

    Kuhio Village 410 Condominium

    Kuhio Village 410 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  23. $129 to $180/night

    Cabana 301 Apartment

    Cabana 301 Apartment

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  24. $111/night

    Aloha Surf 315 Hotel Suites

    Aloha Surf 315 Hotel Suites

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $158 to $191/night

     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. $123 to $180/night

    Hawaiian King 112 Condo

    Hawaiian King 112 Condo

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $122 to $186/night

    Bamboo 308 Condominium

    Bamboo 308 Condominium

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $141/night

    Bamboo 505 Condominium

    Bamboo 505 Condominium

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  29. $456 to $572/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  30. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $356 to $576/night

    Ilikai 526

    Ilikai 526

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $492 to $1,231/night

    Manoa Valley 2BR w/ Hot Tub & Lanai w/ Ocean View

    Manoa Valley 2BR w/ Hot Tub & Lanai w/ Ocean View

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Hot Tub Pets OK
    FREE CANCELLATION
  33. $79 to $139/night

    Discovery Bay 2016

    Discovery Bay 2016

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  34. $118 to $263/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $231 to $377/night

    Maui Kamaole #I-215

    Maui Kamaole #I-215

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $161 to $361/night

    Kaleialoha 309

    Kaleialoha 309

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $359 to $616/night

    Napili Point C-12 2bdrm/2bath

    Napili Point C-12 2bdrm/2bath

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  38. $174 to $347/night

    Maui Kamaole #I-109

    Maui Kamaole #I-109

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $276 to $332/night

    Kahana Sunset D8

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  40. $253 to $309/night

    Kahana Sunset D10

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  41. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  42. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $173 to $431/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $220 to $470/night

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  45. $244 to $383/night

    Palms at Wailea #1604

    Palms at Wailea #1604

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $161 to $208/night

    Kihei Kai Nani #8-363

    Kihei Kai Nani #8-363

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  47. $309 to $366/night

    Kahana Sunset B7

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  48. $214 to $270/night

    Bay Villa 33B2

    Bay Villa 33B2

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  49. $161 to $271/night

    Kaanapali Shores 628

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $132 to $277/night

    Kihei Bay Surf #136

    Kihei Bay Surf #136

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $204 to $413/night

    Maui Kamaole #K-108

    Maui Kamaole #K-108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $208 to $336/night

    Honokeana Cove 103

    Honokeana Cove 103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $208 to $253/night

    Sands Of Kahana 231

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  54. $371 to $484/night

    Kahana Sunset F6

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  55. $106 to $161/night

    KV510 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    KV510 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  56. $110 to $149/night

    KV702 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    KV702 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  57. $1,734 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  58. $231 to $331/night

    Hale Kamaole #101

    Hale Kamaole #101

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $218 to $502/night

    Kaleialoha #113

    Kaleialoha #113

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $681 to $1,717/night

    Wailea Elua #2303

    Wailea Elua #2303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $146 to $363/night

    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  62. $184 to $331/night

    Haleakala Shores #A-208

    Haleakala Shores #A-208

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  63. $234 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $118 to $174/night

    BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH

    BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    Prime Now
    FREE CANCELLATION
  65. $146 to $275/night

    Ilikai 908

    Ilikai 908

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $276 to $332/night

    Kahana Sunset C7

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  67. $186 to $625/night

    Kaanapali Royal B303

    Kaanapali Royal B303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $199 to $583/night

    Kaanapali Royal E101

    Kaanapali Royal E101

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $311 to $965/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  71. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  72. $113 to $161/night

    AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH

    AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  73. $171 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  74. $246 to $464/night

    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $199 to $406/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $171 to $443/night

    Kaleialoha #305

    Kaleialoha #305

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $208 to $347/night

    Menehune Shores #401

    Menehune Shores #401

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. $133 to $244/night

    Kihei Garden Estates #E-102

    Kihei Garden Estates #E-102

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $150 to $219/night

    Kihei Kai Nani #4-221

    Kihei Kai Nani #4-221

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. $219 to $348/night

    Maui Vista #3-404

    Maui Vista #3-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  81. $269 to $409/night

    276

    276

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. $234 to $464/night

    Vista Waikoloa G-104

    Vista Waikoloa G-104

    2 Bedrooms2.5 BathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $82 to $145/night

    Discovery Bay 1815

    Discovery Bay 1815

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  84. $296 to $566/night

    International Colony Club #18

    International Colony Club #18

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  85. $501 to $557/night

    Sands Of Kahana 474

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  86. $199 to $474/night

    Hololani A701

    Hololani A701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $174 to $299/night

    Eldorado J111

    Eldorado J111

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  88. $276 to $332/night

    Kahana Sunset D2

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  89. $347 to $695/night

    Maui Hill #I-99

    Maui Hill #I-99

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $213 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  91. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $294 to $494/night

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  93. $253 to $366/night

    Kahana Sunset B3

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  94. $180 to $209/night

    Shores of Maui #124

    Shores of Maui #124

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $274 to $686/night

    Kaanapali Royal N102

    Kaanapali Royal N102

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $249 to $348/night

    Hale Kamaole #318

    Hale Kamaole #318

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  97. $556 to $927/night

    Hale Ili Ili #D

    Hale Ili Ili #D

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $312 to $428/night

    Wailea Ekolu #1608

    Wailea Ekolu #1608

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  99. $126 to $231/night

    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $102 to $186/night

    Discovery Bay 1309

    Discovery Bay 1309

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION