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. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $379 to $1,385/night

  2. CONDOMINIUM
    Kapalua Ridge Villa #311

    Kapalua Ridge Villa #311

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $464/night

  3. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  4. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $304/night

  5. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  6. APARTMENT
    KV1002 2463 Kuhio Ave Honolulu TH-PTO-00-ACH

    KV1002 2463 Kuhio Ave Honolulu TH-PTO-00-ACH

    Honolulu, HI

    FREE CANCELLATION

    $118 to $140/night

  7. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  8. CONDOMINIUM
    Wailea Ekolu #1207

    Wailea Ekolu #1207

    Wailea, HI

    Pool
    FREE CANCELLATION

    $273 to $463/night

  9. CONDOMINIUM
    Kaanapali Plantation #52

    Kaanapali Plantation #52

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $619/night

  10. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $111 to $284/night

  11. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  12. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $418/night

  13. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $221/night

  14. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $351 to $383/night

  15. CONDOMINIUM
    Maui Vista #1306

    Maui Vista #1306

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $279/night

  16. CONDOMINIUM
    Kamaole Sands #10-405

    Kamaole Sands #10-405

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $480/night

  17. CONDOMINIUM
    Kamaole Sands #01-302

    Kamaole Sands #01-302

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $332/night

  18. CONDOMINIUM
    Hale Mahina #A207

    Hale Mahina #A207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $414/night

  19. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  20. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Pool

    $525 to $1,785/night

  21. HOUSE
    Hoku'Ea Hale

    Hoku'Ea Hale

    Kailua Kona, HI

    Hot Tub

    $609 to $2,136/night

  22. HOUSE
    Elua Honu

    Elua Honu

    Kailua Kona, HI

    $462 to $1,522/night

  23. HOUSE
    Kahalu'u Hale

    Kahalu'u Hale

    Kailua Kona, HI

    Pool

    $396 to $1,248/night

  24. CONDOMINIUM
    Keauhou Surf & Racquet 58

    Keauhou Surf & Racquet 58

    Kailua Kona, HI

    Pool

    $262 to $614/night

  25. CONDOMINIUM
    Maui Vista #2-101

    Maui Vista #2-101

    Kihei, HI

    Pool
    FREE CANCELLATION

    $145 to $231/night

  26. CONDOMINIUM
    268

    268

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  27. CONDOMINIUM
    276

    276

    Kihei, HI

    Pool
    FREE CANCELLATION

    $269 to $409/night

  28. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $370/night

  29. CONDOMINIUM
    Hale Mahina #B403

    Hale Mahina #B403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $600/night

  30. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  31. CONDOMINIUM
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $162 to $579/night

  32. CONDOMINIUM
    Ilikai 815

    Ilikai 815

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $141 to $250/night

  33. CONDOMINIUM
    Ilikai 1118

    Ilikai 1118

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $146 to $262/night

  34. CONDOMINIUM
    Kihei Akahi Resort- Unit C213

    Kihei Akahi Resort- Unit C213

    Kihei, HI

    FREE CANCELLATION

    $161 to $379/night

  35. VILLA
    Wailea Inn Maui

    Wailea Inn Maui

    Kihei, HI

    $3,248 to $5,568/night

  36. CONDOMINIUM
    Ali'i Kai 2201

    Ali'i Kai 2201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $96 to $331/night

  37. CONDOMINIUM
    Puu Poa 309

    Puu Poa 309

    Princeville, HI

    Pool
    FREE CANCELLATION

    $402 to $804/night

  38. CONDOMINIUM
    Lahaina Roads 309

    Lahaina Roads 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $213 to $438/night

  39. CONDOMINIUM
    Island Surf 306

    Island Surf 306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $161 to $281/night

  40. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  41. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $500/night

  42. CONDOMINIUM
    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua, HI

    Pool

    $294 to $494/night

  43. CONDOMINIUM
    Wailea Ekolu #201

    Wailea Ekolu #201

    Wailea, HI

    Pool
    FREE CANCELLATION

    $290 to $487/night

  44. CONDOMINIUM
    Wavecrest B209

    Wavecrest B209

    Ualapue, HI

    FREE CANCELLATION

    $113 to $152/night

  45. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  46. CONDOMINIUM
    Maui Kaanapali Villas #A317

    Maui Kaanapali Villas #A317

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $348/night

  47. CONDOMINIUM
    Kahana Villas #F507

    Kahana Villas #F507

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $267 to $532/night

  48. CONDOMINIUM
    Kamaole Sands #06-106

    Kamaole Sands #06-106

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $332/night

  49. CONDOMINIUM
    Maui Vista #1120

    Maui Vista #1120

    KIHEI, HI

    Pool
    FREE CANCELLATION

    $241 to $279/night

  50. CONDOMINIUM
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $602 to $764/night

  51. APARTMENT
    KV1201L 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    KV1201L 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

    Honolulu, HI

    FREE CANCELLATION

    $110 to $163/night

  52. CONDOMINIUM
    WPH1801 2440 Kuhio Ave Honolulu THTC-CTOQ(XS)-01M-ACH

    WPH1801 2440 Kuhio Ave Honolulu THTC-CTOQ(XS)-01M-ACH

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $199 to $249/night

  53. CONDOMINIUM
    Maui Banyan Q306

    Maui Banyan Q306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $130 to $406/night

  54. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  55. CONDOMINIUM
    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To Beach

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    Kihei, HI

    Pool Hot Tub

    $347 to $786/night

  56. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $452 to $926/night

  57. CONDOMINIUM
    Maui Eldorado Condo G101

    Maui Eldorado Condo G101

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $169 to $395/night

  58. CONDOMINIUM
    Discovery Bay 1309

    Discovery Bay 1309

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $102 to $186/night

  59. CONDOMINIUM
    Maui Eldorado Condo F201

    Maui Eldorado Condo F201

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $250 to $596/night

  60. CONDOMINIUM
    Maui Eldorado Condo K207

    Maui Eldorado Condo K207

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $207 to $501/night

  61. CONDOMINIUM
    Maui Eldorado Condo A104

    Maui Eldorado Condo A104

    Kaanapali, HI

    Pool
    FREE CANCELLATION

    $262 to $565/night

  62. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $114 to $399/night

  63. HOUSE
    Oceanfront 3BR, Breathtaking Views

    Oceanfront 3BR, Breathtaking Views

    Captain Cook, HI

    FREE CANCELLATION

    $203 to $522/night

  64. CONDOMINIUM
    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $118 to $263/night

  65. HOUSE
    Malolo Cottage

    Malolo Cottage

    Hanalei, HI

    FREE CANCELLATION

    $249 to $312/night

  66. CONDOMINIUM
    Plantations 111

    Plantations 111

    Princeville, HI

    Pool

    $206 to $332/night

  67. HOUSE
    Moloa'a Bay Villa

    Moloa'a Bay Villa

    Kilauea, HI

    $1,208 to $1,413/night

  68. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Kilauea, HI

    $1,413 to $1,906/night

  69. CONDOMINIUM
    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    Kapaa, HI

    $311 to $429/night

  70. COTTAGE
    Moloa'a Bay Cottage

    Moloa'a Bay Cottage

    Kilauea, HI

    $430 to $514/night

  71. CONDOMINIUM
    Pali Ke Kua 103

    Pali Ke Kua 103

    Princeville, HI

    Pool

    $365 to $458/night

  72. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $604/night

  73. CONDOMINIUM
    Pali Ke Kua 241

    Pali Ke Kua 241

    Princeville, HI

    Pool

    $241 to $311/night

  74. TOWNHOUSE
    Puamana 15-3

    Puamana 15-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $449/night

  75. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  76. CONDOMINIUM
    Hololani A701

    Hololani A701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $204 to $474/night

  77. CONDOMINIUM
    Kahana Sunset B3

    Kahana Sunset B3

    Lahaina, HI

    Pool

    $253 to $366/night

  78. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  79. CONDOMINIUM
    Shores of Maui #211

    Shores of Maui #211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $335/night

  80. CONDOMINIUM
    Unit 213

    Unit 213

    Lahaina, HI

    FREE CANCELLATION

    $196 to $284/night

  81. CONDOMINIUM
    Unit 114

    Unit 114

    Lahaina, HI

    FREE CANCELLATION

    $249 to $302/night

  82. CONDOMINIUM
    147

    147

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  83. CONDOMINIUM
    141

    141

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  84. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $337/night

  85. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $465/night

  86. CONDOMINIUM
    Kauhale Makai #331

    Kauhale Makai #331

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $326/night

  87. CONDOMINIUM
    Ewa Hotel Waikiki #507

    Ewa Hotel Waikiki #507

    Honolulu, HI

    FREE CANCELLATION

    $194 to $563/night

  88. CONDOMINIUM
    Pohailani #201

    Pohailani #201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $249/night

  89. CONDOMINIUM
    Pikake #A2

    Pikake #A2

    Lahaina, HI

    FREE CANCELLATION

    $215 to $363/night

  90. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $435/night

  91. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $128 to $249/night

  92. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  93. CONDOMINIUM
    Turtle Bay Pupukea***NUC 90-TVU-0246

    Turtle Bay Pupukea***NUC 90-TVU-0246

    Kahuku, HI

    Pool
    FREE CANCELLATION
  94. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  95. CONDOMINIUM
    Unit 214

    Unit 214

    Lahaina, HI

    FREE CANCELLATION

    $249 to $302/night

  96. APARTMENT
    KV702 2463 Kuhio Ave Honolulu THTH-PTO-00-ACH

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

    Honolulu, HI

    FREE CANCELLATION

    $110 to $149/night

  97. CONDOMINIUM
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    Ilikai Tower 420

    1 Bedroom Deluxe Lagoon View on the 4th Floor!

    Modern and elegant in style, this updated unit will ensure a comfortable and luxurious stay at the Ilikai. Whether you're enjoying watching the sun rise over the ocean from the lanai, or a

    Multiple properties, see more below

    Ilikai Tower 931

    Honolulu, HI

    1 Bedroom | 1 Bathroom | Sleeps 4   Pool

    FREE CANCELLATION

    1 Bedroom Deluxe Yacht Harbor View on the 9th Floor! This unit features tile flooring throughout, a full, renovated kitchen, a king bed and pull-out sofa bed, and free wifi. This unit also boasts a lanai overlooking the yacht harbor and Pacific...

  98. CONDOMINIUM
    Discovery Bay 2016

    Discovery Bay 2016

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $79 to $139/night

  99. CONDOMINIUM
    Kamaole Sands #03-401

    Kamaole Sands #03-401

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $371 to $458/night

  100. CONDOMINIUM
    Kauhale Makai #627

    Kauhale Makai #627

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $326/night