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. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

  2. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  3. CONDOMINIUM
    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $242 to $309/night

  4. CONDOMINIUM
    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Honolulu, HI

    FREE CANCELLATION

    $174 to $731/night

  5. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  6. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  7. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $193 to $306/night

  8. CONDOMINIUM
    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    Lahaina, HI

    Pool

    $594 to $1,063/night

  9. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $251 to $348/night

  10. CONDOMINIUM
    Keauhou Kona Surf & Racquet Townhouse #36

    Keauhou Kona Surf & Racquet Townhouse #36

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $267 to $400/night

  11. CONDOMINIUM
    Paki Maui 415

    Paki Maui 415

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $375/night

  12. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  13. CONDOMINIUM
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $333 to $703/night

  14. CONDOMINIUM
    Kahana Sunset E6

    Kahana Sunset E6

    Lahaina, HI

    Pool

    $276 to $332/night

  15. CONDOMINIUM
    Kahana Sunset B1

    Kahana Sunset B1

    Lahaina, HI

    Pool

    $253 to $309/night

  16. CONDOMINIUM
    Kona Reef D32

    Kona Reef D32

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $292/night

  17. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  18. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $238 to $257/night

  19. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  20. CONDOMINIUM
    Kahana Sunset B5B

    Kahana Sunset B5B

    Lahaina, HI

    Pool

    $214 to $270/night

  21. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  22. CONDOMINIUM
    Kahana Sunset E8

    Kahana Sunset E8

    Lahaina, HI

    Pool

    $276 to $332/night

  23. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  24. CONDOMINIUM
    Kahana Sunset A5

    Kahana Sunset A5

    Lahaina, HI

    Pool

    $428 to $484/night

  25. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  26. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  27. CONDOMINIUM
    107

    107

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  28. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  29. CONDOMINIUM
    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $617/night

  30. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $571 to $1,789/night

  31. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  32. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  33. CONDOMINIUM
    Valley Isle 204

    Valley Isle 204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $363/night

  34. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $813/night

  35. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Pool
    FREE CANCELLATION

    $257 to $361/night

  36. CONDOMINIUM
    Kalani Kai 105

    Kalani Kai 105

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $99 to $350/night

  37. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  38. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  39. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $348 to $451/night

  40. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Pool

    $887 to $1,138/night

  41. CONDOMINIUM
    Kahana Sunset C5

    Kahana Sunset C5

    Lahaina, HI

    Pool

    $276 to $332/night

  42. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,209/night

  43. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $354 to $410/night

  44. CONDOMINIUM
    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    Koloa, HI

    Pool Hot Tub

    $289 to $394/night

  45. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,209/night

  46. CONDOMINIUM
    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $431/night

  47. CONDOMINIUM
    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $192 to $252/night

  48. CONDOMINIUM
    Palm Leaf

    Palm Leaf

    Kamuela, HI

    Pool Hot Tub

    $238 to $598/night

  49. CONDOMINIUM
    Kahana Sunset B8

    Kahana Sunset B8

    Lahaina, HI

    Pool

    $309 to $366/night

  50. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  51. HOUSE
    Plantation Cottage

    Plantation Cottage

    Hanalei, HI

    FREE CANCELLATION

    $392 to $523/night

  52. CONDOMINIUM
    Kona Bali Kai Studio w/ Pool & Spa

    Kona Bali Kai Studio w/ Pool & Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $61 to $269/night

  53. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $324/night

  54. CONDOMINIUM
    Mauna Kai 5A

    Mauna Kai 5A

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  55. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    FREE CANCELLATION

    $163 to $239/night

  56. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  57. CONDOMINIUM
    Kona Isle B31

    Kona Isle B31

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $152 to $244/night

  58. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  59. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  60. HOUSE
    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    Honolulu, HI

    FREE CANCELLATION

    $325 to $786/night

  61. CONDOMINIUM
    Kapalua Bay Villa 12G5 Ocean View

    Kapalua Bay Villa 12G5 Ocean View

    Kapalua, HI

    Pool

    $288 to $494/night

  62. CONDOMINIUM
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    Pool

    $781 to $1,219/night

  63. CONDOMINIUM
    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua, HI

    Pool

    $294 to $563/night

  64. CONDOMINIUM
    Kapalua Golf Villa 11T4 Ocean View

    Kapalua Golf Villa 11T4 Ocean View

    Kapalua, HI

    Pool

    $281 to $494/night

  65. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  66. CONDOMINIUM
    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua, HI

    Pool

    $294 to $494/night

  67. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool
  68. CONDOMINIUM
    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $476/night

  69. CONDOMINIUM
    Lauloa 105

    Lauloa 105

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $211 to $438/night

  70. CONDOMINIUM
    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $431/night

  71. CONDOMINIUM
    Kona Plaza#220

    Kona Plaza#220

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $139 to $207/night

  72. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  73. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  74. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  75. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  76. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Pool Hot Tub

    $1,635 to $2,364/night

  77. HOUSE
    New Listing! Hawaiian Experience- Walk to Two Step

    New Listing! Hawaiian Experience- Walk to Two Step

    Captain Cook, HI

    Pets OK
    FREE CANCELLATION

    $218 to $271/night

  78. CONDOMINIUM
    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua, HI

    Pool

    $481 to $856/night

  79. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,174/night

  80. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $508 to $988/night

  81. CONDOMINIUM
    Hale Ono Loa 402

    Hale Ono Loa 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $331/night

  82. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  83. CONDOMINIUM
    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  84. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,789/night

  85. CONDOMINIUM
    Maui Vista 2211

    Maui Vista 2211

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $386/night

  86. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  87. CONDOMINIUM
    Alii Kai #2104

    Alii Kai #2104

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  88. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  89. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $132 to $304/night

  90. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  91. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  92. CONDOMINIUM
    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,673/night

  93. CONDOMINIUM
    Kaanapali Shores 546

    Kaanapali Shores 546

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $170 to $441/night

  94. CONDOMINIUM
    Turtle Bay Hale Kai***NUC90-TVU-0746 Available for 2 people only

    Turtle Bay Hale Kai***NUC90-TVU-0746 Available for 2 peo...

    Kahuku, HI

    Pool
    FREE CANCELLATION
  95. CONDOMINIUM
    Turtle Bay Deep Blue**NUC 90-TVU-0523

    Turtle Bay Deep Blue**NUC 90-TVU-0523

    Kahuku, HI

    Pool
    FREE CANCELLATION
  96. CONDOMINIUM
    Turtle Bay Alea**NUC 90-TVU-0263

    Turtle Bay Alea**NUC 90-TVU-0263

    Kahuku, HI

    Pool
    FREE CANCELLATION
  97. CONDOMINIUM
    Hanalei Colony G1

    Hanalei Colony G1

    Haena, HI

    FREE CANCELLATION

    $374 to $499/night

  98. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  99. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  100. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night