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
    Ka Hale Kaeloha (House of Love) – Romantic Oceanside Condo

    Ka Hale Kaeloha (House of Love) – Romantic Oceanside C...

    Kaunakakai, HI

    Pool Pets OK
    FREE CANCELLATION

    $158 to $191/night

  2. CONDOMINIUM
    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $262 to $776/night

  3. VILLA
    Kahana Villa E614

    Kahana Villa E614

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $776/night

  4. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  5. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  6. CONDOMINIUM
    Nani Kai Hale # 507

    Nani Kai Hale # 507

    Kihei, HI

    Pool
    FREE CANCELLATION

    $141 to $208/night

  7. CONDOMINIUM
    Nani Kai Hale # 409

    Nani Kai Hale # 409

    Kihei, HI

    FREE CANCELLATION

    $253 to $276/night

  8. CONDOMINIUM
    Cottage 2B

    Cottage 2B

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $225 to $281/night

  9. CONDOMINIUM
    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $244/night

  10. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $183/night

  11. CONDOMINIUM
    Waiohuli Beach Hale #B-205

    Waiohuli Beach Hale #B-205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  12. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  13. CONDOMINIUM
    Hale Kamaole #201

    Hale Kamaole #201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $300 to $358/night

  14. HOUSE
    New Listing! “Kona Sunset Hale” w/ Ocean Views

    New Listing! “Kona Sunset Hale” w/ Ocean Views

    Kailua Kona, HI

    FREE CANCELLATION

    $166 to $465/night

  15. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $458/night

  16. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $273/night

  17. CONDOMINIUM
    123

    123

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  18. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $429/night

  19. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $348/night

  20. CONDOMINIUM
    Kihei Kai Nani #2-210

    Kihei Kai Nani #2-210

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $208/night

  21. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

  22. CONDOMINIUM
    Kihei Kai Nani #3-116

    Kihei Kai Nani #3-116

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $244/night

  23. CONDOMINIUM
    Wavecrest C205

    Wavecrest C205

    Ualapue, HI

    FREE CANCELLATION

    $113 to $152/night

  24. CONDOMINIUM
    Waiohuli Beach Hale #B-107

    Waiohuli Beach Hale #B-107

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  25. CONDOMINIUM
    203

    203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  26. CONDOMINIUM
    Kihei Garden Estates #A-102

    Kihei Garden Estates #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $196/night

  27. CONDOMINIUM
    206

    206

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  28. CONDOMINIUM
    Waiohuli Beach Hale #D-118

    Waiohuli Beach Hale #D-118

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  29. CONDOMINIUM
    111

    111

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  30. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Pool Hot Tub

    $162 to $401/night

  31. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $360/night

  32. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  33. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $521/night

  34. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  35. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  36. CONDOMINIUM
    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    Kapalua, HI

    Pool

    $525 to $869/night

  37. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $359/night

  38. CONDOMINIUM
    Royal Kahana 409 1 Bdrm

    Royal Kahana 409 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $563/night

  39. COTTAGE
    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Honolulu, HI

    FREE CANCELLATION

    $135 to $454/night

  40. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool Hot Tub

    $259 to $335/night

  41. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool Hot Tub

    $259 to $361/night

  42. CONDOMINIUM
    Turtle Bay Hale Lilly**NUC 90-TVU-0350

    Turtle Bay Hale Lilly**NUC 90-TVU-0350

    Kahuku, HI

    Pool
    FREE CANCELLATION
  43. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  44. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  45. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $502/night

  46. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $189 to $502/night

  47. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $502/night

  48. CONDOMINIUM
    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    Koloa, HI

    Pool Hot Tub

    $392 to $514/night

  49. CONDOMINIUM
    Kona Makai 3-203

    Kona Makai 3-203

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $239/night

  50. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 5-304

    Keauhou Kona Surf and Racquet Club 5-304

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $651 to $717/night

  51. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $311 to $350/night

  52. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  53. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 3202

    Keauhou Kona Surf & Racquet Club 3202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $349 to $350/night

  54. CONDOMINIUM
    Kona Isle C24

    Kona Isle C24

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $111 to $140/night

  55. CONDOMINIUM
    Sealodge E10

    Sealodge E10

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  56. CONDOMINIUM
    Palms at Wailea #1005

    Palms at Wailea #1005

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $303 to $538/night

  57. CONDOMINIUM
    Grand Champions #50

    Grand Champions #50

    Wailea, HI

    Pool
    FREE CANCELLATION

    $230 to $409/night

  58. CONDOMINIUM
    Waiohuli Beach Hale #D-114

    Waiohuli Beach Hale #D-114

    Kihei, HI

    Pool
    FREE CANCELLATION

    $181 to $317/night

  59. CONDOMINIUM
    Palms at Wailea #702

    Palms at Wailea #702

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $262 to $462/night

  60. CONDOMINIUM
    Leinaala Oceanfront #105

    Leinaala Oceanfront #105

    Kihei, HI

    Pool
    FREE CANCELLATION

    $252 to $448/night

  61. CONDOMINIUM
    Grand Champions #151

    Grand Champions #151

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $218 to $389/night

  62. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $262 to $464/night

  63. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $282 to $502/night

  64. CONDOMINIUM
    Kamaole Sands #1-406

    Kamaole Sands #1-406

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $442/night

  65. CONDOMINIUM
    Waiohuli Beach Hale #D-223

    Waiohuli Beach Hale #D-223

    Kihei, HI

    Pool
    FREE CANCELLATION

    $206 to $367/night

  66. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $273 to $485/night

  67. CONDOMINIUM
    Wailea Ekolu #406

    Wailea Ekolu #406

    Wailea, HI

    Pool
    FREE CANCELLATION

    $296 to $521/night

  68. CONDOMINIUM
    Valley Isle #1104

    Valley Isle #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $375/night

  69. CONDOMINIUM
    Islander on the Beach 259

    Islander on the Beach 259

    Kapaa, HI

    Pool
    FREE CANCELLATION
  70. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  71. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  72. CONDOMINIUM
    Puamana 9C

    Puamana 9C

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  73. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $361 to $479/night

  74. CONDOMINIUM
    Kona Pacific

    Kona Pacific

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $146 to $183/night

  75. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  76. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    $1,661 to $2,429/night

  77. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  78. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  79. CONDOMINIUM
    Nohonani #402

    Nohonani #402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  80. CONDOMINIUM
    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    Lahaina, HI

    FREE CANCELLATION

    $217 to $604/night

  81. CONDOMINIUM
    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    Honolulu, HI

    FREE CANCELLATION

    $178 to $248/night

  82. CONDOMINIUM
    Napili Shores F147

    Napili Shores F147

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $202 to $636/night

  83. CONDOMINIUM
    Turtle Bay Wicked Wahine***TA-129213644801

    Turtle Bay Wicked Wahine***TA-129213644801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  84. CONDOMINIUM
    Naupaka- Kahuku Condo

    Naupaka- Kahuku Condo

    Kahuku, HI

    Pool
    FREE CANCELLATION

    $149 to $237/night

  85. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  86. CONDOMINIUM
    Nani Kai Hale # 301

    Nani Kai Hale # 301

    Kihei, HI

    FREE CANCELLATION

    $141 to $197/night

  87. CONDOMINIUM
    Nani Kai Hale # 405

    Nani Kai Hale # 405

    Kihei, HI

    FREE CANCELLATION

    $152 to $219/night

  88. CONDOMINIUM
    Nani Kai Hale # 308

    Nani Kai Hale # 308

    Kihei, HI

    Pool
    FREE CANCELLATION

    $203 to $264/night

  89. CONDOMINIUM
    Nani Kai Hale # 609

    Nani Kai Hale # 609

    Kihei, HI

    Pool
    FREE CANCELLATION

    $264 to $298/night

  90. CONDOMINIUM
    Aina Nalu Premier Platinum Condo H206

    Aina Nalu Premier Platinum Condo H206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $609/night

  91. CONDOMINIUM
    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lahaina, HI

    FREE CANCELLATION

    $247 to $291/night

  92. CONDOMINIUM
    Wavecrest A109

    Wavecrest A109

    Ualapue, HI

    Pool
    FREE CANCELLATION

    $124 to $169/night

  93. CONDOMINIUM
    Kihei Bay Vista #A-201

    Kihei Bay Vista #A-201

    Kihei, HI

    Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  94. CONDOMINIUM
    207

    207

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  95. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $132 to $304/night

  96. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  97. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  98. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  99. CONDOMINIUM
    Sea Village 3-212

    Sea Village 3-212

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $157 to $242/night

  100. CONDOMINIUM
    266

    266

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night