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
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  2. 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

  3. CONDOMINIUM
    Turtle Bay Hanalei***TA-147868876801

    Turtle Bay Hanalei***TA-147868876801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  4. CONDOMINIUM
    Turtle Bay Pineapple Delight**TA088724684801

    Turtle Bay Pineapple Delight**TA088724684801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  5. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  6. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  7. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  8. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  9. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  10. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

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

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $363/night

  12. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  13. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  14. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $443/night

  15. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  16. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $164 to $183/night

  17. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  18. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $502/night

  19. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $502/night

  20. CONDOMINIUM
    Casa De Emdeko 332

    Casa De Emdeko 332

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  21. CONDOMINIUM
    Kona Isle E23

    Kona Isle E23

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $198 to $326/night

  22. 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 $384/night

  23. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  24. CONDOMINIUM
    Pali Ke Kua #103

    Pali Ke Kua #103

    Princeville, HI

    Pool Hot Tub

    $375 to $459/night

  25. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  26. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  27. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  28. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $291/night

  29. CONDOMINIUM
    Pali Ke Kua #241

    Pali Ke Kua #241

    Princeville, HI

    Pool Hot Tub

    $241 to $313/night

  30. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $609/night

  31. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  32. HOUSE
    Moloa'a Bay Villa

    Moloa'a Bay Villa

    Anahola, HI

    $1,094 to $1,413/night

  33. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  34. CONDOMINIUM
    Alii Villas 340

    Alii Villas 340

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $273 to $292/night

  35. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $337/night

  36. CONDOMINIUM
    Kona Magic Sands 313

    Kona Magic Sands 313

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $312/night

  37. CONDOMINIUM
    Kona Isle D4

    Kona Isle D4

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $224 to $326/night

  38. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $463/night

  39. 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 $409/night

  40. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $641 to $934/night

  41. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  42. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  43. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $308/night

  44. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  45. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  46. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $224/night

  47. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  48. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  49. 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

  50. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  51. 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

  52. CONDOMINIUM
    Nohonani #402

    Nohonani #402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  53. CONDOMINIUM
    Kona Pacific

    Kona Pacific

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $146 to $183/night

  54. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  55. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  56. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  57. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  58. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool Hot Tub

    $259 to $361/night

  59. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $359/night

  60. 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

  61. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $502/night

  62. CONDOMINIUM
    Kona Isle C24

    Kona Isle C24

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $111 to $140/night

  63. CONDOMINIUM
    Sealodge E10

    Sealodge E10

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  64. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool Hot Tub

    $259 to $335/night

  65. CONDOMINIUM
    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    Koloa, HI

    Pool Hot Tub

    $371 to $514/night

  66. CONDOMINIUM
    Valley Isle #1104

    Valley Isle #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $375/night

  67. 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

  68. CONDOMINIUM
    Kona Makai 3-203

    Kona Makai 3-203

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $239/night

  69. 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

  70. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 3202

    Keauhou Kona Surf & Racquet Club 3202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $349 to $350/night

  71. CONDOMINIUM
    Islander on the Beach 259

    Islander on the Beach 259

    Kapaa, HI

    Pool
    FREE CANCELLATION
  72. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $183/night

  73. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  74. CONDOMINIUM
    Puamana 9C

    Puamana 9C

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  75. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  76. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  77. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  78. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

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

    Turtle Bay Wicked Wahine***TA-129213644801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  80. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  81. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  82. CONDOMINIUM
    Papakea E306

    Papakea E306

    Lahaina, HI

    Pool Hot Tub

    $183 to $314/night

  83. CONDOMINIUM
    Kanaloa 202

    Kanaloa 202

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $169 to $230/night

  84. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool Hot Tub

    $270 to $341/night

  85. CONDOMINIUM
    Sea Village 3-212

    Sea Village 3-212

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $157 to $242/night

  86. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $502/night

  87. CONDOMINIUM
    Kona Isle B31

    Kona Isle B31

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $152 to $244/night

  88. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $186 to $239/night

  89. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool Hot Tub

    $299 to $452/night

  90. CONDOMINIUM
    Pali Ke Kua #118

    Pali Ke Kua #118

    Princeville, HI

    Pool Hot Tub

    $247 to $282/night

  91. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $467/night

  92. CONDOMINIUM
    Puu Poa #305

    Puu Poa #305

    Princeville, HI

    Pool

    $334 to $416/night

  93. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool Hot Tub

    $456 to $652/night

  94. HOUSE
    Kauai Tree House

    Kauai Tree House

    Wainiha, HI

    $334 to $398/night

  95. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $239 to $348/night

  96. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  97. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $309 to $326/night

  98. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  99. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night