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
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $158 to $191/night

  2. CONDOMINIUM
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  3. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  4. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  5. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  6. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $347/night

  7. CONDOMINIUM
    Keawakapu Views #206

    Keawakapu Views #206

    Kihei, HI

    FREE CANCELLATION

    $157 to $261/night

  8. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  9. CONDOMINIUM
    Kihei Bay Surf #253

    Kihei Bay Surf #253

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  10. CONDOMINIUM
    Kihei Bay Vista #D-208

    Kihei Bay Vista #D-208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $219/night

  11. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  12. CONDOMINIUM
    Pacific Shores #A-101

    Pacific Shores #A-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $244/night

  13. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  14. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $347/night

  15. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $581 to $1,215/night

  16. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  17. CONDOMINIUM
    117

    117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  18. CONDOMINIUM
    128

    128

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  19. CONDOMINIUM
    Alii Villas 340

    Alii Villas 340

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $212 to $274/night

  20. CONDOMINIUM
    Casa De Emdeko 332

    Casa De Emdeko 332

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $196 to $239/night

  21. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  22. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $266/night

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

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $383 to $404/night

  24. CONDOMINIUM
    Kona Isle D4

    Kona Isle D4

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $218 to $222/night

  25. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  26. CONDOMINIUM
    Kihei Bay Surf #123

    Kihei Bay Surf #123

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  27. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  28. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  29. CONDOMINIUM
    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    Kihei, HI

    Pool
    FREE CANCELLATION

    $198 to $481/night

  30. CONDOMINIUM
    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $472/night

  31. CONDOMINIUM
    Menehune Shores #401

    Menehune Shores #401

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  32. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $164 to $183/night

  33. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  34. CONDOMINIUM
    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  35. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $855/night

  36. CONDOMINIUM
    Shores of Maui #211

    Shores of Maui #211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $335/night

  37. CONDOMINIUM
    Leinaala Oceanfront #301

    Leinaala Oceanfront #301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $200 to $481/night

  38. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $233 to $561/night

  39. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  40. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  41. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  42. CONDOMINIUM
    Waiohuli Beach Hale #C-112

    Waiohuli Beach Hale #C-112

    Kihei, HI

    Pool
    FREE CANCELLATION

    $223 to $535/night

  43. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  44. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  45. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $214/night

  46. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  47. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  48. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  49. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  50. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  51. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  52. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  53. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  54. CONDOMINIUM
    Wailea Ekolu #911

    Wailea Ekolu #911

    Wailea, HI

    Pool
    FREE CANCELLATION

    $231 to $347/night

  55. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  56. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  57. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  58. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $488/night

  59. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $209/night

  60. CONDOMINIUM
    Leinaala Oceanfront #405

    Leinaala Oceanfront #405

    Kihei, HI

    Pool
    FREE CANCELLATION

    $300 to $720/night

  61. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  62. CONDOMINIUM
    Puu Poa #305

    Puu Poa #305

    Princeville, HI

    Pool

    $334 to $375/night

  63. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool

    $270 to $305/night

  64. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night

  65. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  66. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $428/night

  67. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $632/night

  68. CONDOMINIUM
    Maui Kamaole #F-210

    Maui Kamaole #F-210

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $360/night

  69. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  70. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  71. CONDOMINIUM
    236

    236

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  72. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $633/night

  73. CONDOMINIUM
    205

    205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  74. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $465 to $486/night

  75. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  76. CONDOMINIUM
    Maui Sunset #B-106

    Maui Sunset #B-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $414/night

  77. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  78. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $209 to $506/night

  79. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $802/night

  80. CONDOMINIUM
    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $378/night

  81. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  82. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  83. HOUSE
    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    Wailea, Maui, HI

    Pool

    $616 to $1,065/night

  84. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  85. CONDOMINIUM
    133

    133

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  86. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $257/night

  87. CONDOMINIUM
    Kona Magic Sands 313

    Kona Magic Sands 313

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $270 to $358/night

  88. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $632 to $1,015/night

  89. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $162 to $413/night

  90. CONDOMINIUM
    Kona Isle E23

    Kona Isle E23

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $187 to $198/night

  91. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  92. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  93. CONDOMINIUM
    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    Lahaina, HI

    FREE CANCELLATION

    $217 to $604/night

  94. CONDOMINIUM
    Aina Nalu Premier Platinum Condo H206

    Aina Nalu Premier Platinum Condo H206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $591/night

  95. CONDOMINIUM
    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    Honolulu, HI

    FREE CANCELLATION

    $178 to $248/night

  96. CONDOMINIUM
    Napili Shores F147

    Napili Shores F147

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $236 to $510/night

  97. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  98. CONDOMINIUM
    Menehune Shores #425

    Menehune Shores #425

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  99. CONDOMINIUM
    Waiohuli Beach Hale #D-124

    Waiohuli Beach Hale #D-124

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  100. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night