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. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  2. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  3. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  4. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    $1,661 to $2,429/night

  5. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  6. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  7. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  8. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  9. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

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

    Keauhou Kona Surf and Racquet Club 5-304

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $650 to $718/night

  11. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $632 to $1,015/night

  12. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  13. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $571 to $1,115/night

  14. CONDOMINIUM
    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Pool

    $556 to $1,063/night

  15. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  16. 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

  17. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  18. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  19. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $493 to $922/night

  20. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  21. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  22. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  23. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  24. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  25. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool

    $456 to $543/night

  26. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night

  27. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  28. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $420 to $465/night

  29. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  30. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  31. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  32. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $579/night

  33. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $849/night

  34. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $421/night

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

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $350 to $384/night

  36. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 3202

    Keauhou Kona Surf & Racquet Club 3202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $349 to $350/night

  37. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  38. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $521/night

  39. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $544/night

  40. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  41. CONDOMINIUM
    Puu Poa #305

    Puu Poa #305

    Princeville, HI

    Pool

    $334 to $375/night

  42. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $796/night

  43. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  44. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $325 to $337/night

  45. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  46. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  47. 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

  48. CONDOMINIUM
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  49. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $458/night

  50. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  51. CONDOMINIUM
    Hale Kamaole #201

    Hale Kamaole #201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $300 to $358/night

  52. CONDOMINIUM
    Leinaala Oceanfront #405

    Leinaala Oceanfront #405

    Kihei, HI

    Pool
    FREE CANCELLATION

    $300 to $716/night

  53. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool

    $299 to $415/night

  54. CONDOMINIUM
    Wailea Ekolu #406

    Wailea Ekolu #406

    Wailea, HI

    Pool
    FREE CANCELLATION

    $296 to $521/night

  55. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

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

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

    Kahuku, HI

    Pool
    FREE CANCELLATION
  57. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $280 to $309/night

  58. CONDOMINIUM
    Palms at Wailea #1005

    Palms at Wailea #1005

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $664/night

  59. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  60. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  61. CONDOMINIUM
    Nohonani #402

    Nohonani #402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  62. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  63. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool

    $270 to $305/night

  64. CONDOMINIUM
    Kauai Beach Villas 2 Bedroom

    Kauai Beach Villas 2 Bedroom

    Lihue, HI

    Pool
  65. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $347/night

  66. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $259 to $618/night

  67. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  68. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  69. CONDOMINIUM
    221

    221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  70. CONDOMINIUM
    266

    266

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  71. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $488/night

  72. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  73. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool

    $256 to $344/night

  74. CONDOMINIUM
    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $461/night

  75. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $255 to $610/night

  76. CONDOMINIUM
    Palms at Wailea #604

    Palms at Wailea #604

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $466/night

  77. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $251 to $389/night

  78. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $429/night

  79. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $249 to $596/night

  80. VILLA
    Kahana Villa E614

    Kahana Villa E614

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $248 to $641/night

  81. CONDOMINIUM
    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $247 to $649/night

  82. CONDOMINIUM
    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lahaina, HI

    FREE CANCELLATION

    $247 to $291/night

  83. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  84. CONDOMINIUM
    Palms at Wailea #702

    Palms at Wailea #702

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $242 to $570/night

  85. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $570/night

  86. CONDOMINIUM
    Pali Ke Kua #241

    Pali Ke Kua #241

    Princeville, HI

    Pool

    $241 to $276/night

  87. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

  88. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  89. CONDOMINIUM
    Royal Kahana 409 1 Bdrm

    Royal Kahana 409 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $551/night

  90. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  91. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  92. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  93. CONDOMINIUM
    Napili Shores F147

    Napili Shores F147

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $236 to $510/night

  94. CONDOMINIUM
    203

    203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  95. CONDOMINIUM
    311

    311

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  96. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  97. 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

  98. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  99. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $233 to $557/night

  100. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night