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
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  2. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  3. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  4. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  5. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  6. CONDOMINIUM
    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $118 to $267/night

  7. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $117 to $414/night

  8. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  9. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

  10. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  11. 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

    $175 to $632/night

  12. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $489/night

  13. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  14. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  15. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $474/night

  16. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $213 to $446/night

  17. CONDOMINIUM
    Aina Nalu G204

    Aina Nalu G204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $236 to $455/night

  18. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $498/night

  19. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $239/night

  20. CONDOMINIUM
    Aina Nalu K102

    Aina Nalu K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $449/night

  21. CONDOMINIUM
    Alii Kai 3103

    Alii Kai 3103

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $293/night

  22. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  23. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  24. CONDOMINIUM
    Alii Kai II 8H

    Alii Kai II 8H

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  25. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  26. CONDOMINIUM
    Banyan Tree 404D

    Banyan Tree 404D

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION
  27. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  28. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $165 to $186/night

  29. CONDOMINIUM
    Casa De Emdeko 219

    Casa De Emdeko 219

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  30. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $336 to $337/night

  31. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  32. 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

  33. APARTMENT
    Condo with Ocean View! Right on a Golf Course & Minutes from the Beach!

    Condo with Ocean View! Right on a Golf Course & Minu...

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $140 to $213/night

  34. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  35. CONDOMINIUM
    Eldorado E104

    Eldorado E104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $480/night

  36. CONDOMINIUM
    Eldorado J109

    Eldorado J109

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $299/night

  37. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  38. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $618/night

  39. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $641/night

  40. CONDOMINIUM
    Eldorado K203

    Eldorado K203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $500/night

  41. HOUSE
    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $536/night

  42. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  43. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  44. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $134 to $213/night

  45. CONDOMINIUM
    Hale 'Olu'Olu

    Hale 'Olu'Olu

    Waikoloa, HI

    Pool

    $238 to $478/night

  46. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  47. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  48. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,384/night

  49. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  50. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $455 to $1,500/night

  51. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,500/night

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

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $559 to $1,784/night

  53. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

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

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,784/night

  55. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $186 to $275/night

  56. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  57. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  58. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,016/night

  59. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,384/night

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

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

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

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $466 to $1,384/night

  62. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  63. CONDOMINIUM
    Hale Mahina A-403

    Hale Mahina A-403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $234 to $521/night

  64. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

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

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

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

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $490 to $1,668/night

  67. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $330/night

  68. CONDOMINIUM
    Hale Mali'e

    Hale Mali'e

    Waikoloa, HI

    Pool

    $294 to $598/night

  69. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  70. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  71. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,268/night

  72. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Pool Hot Tub

    $548 to $2,016/night

  73. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  74. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Pool Hot Tub

    $286 to $478/night

  75. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  76. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $454/night

  77. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $314/night

  78. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $995/night

  79. CONDOMINIUM
    Hale Ono Loa 205

    Hale Ono Loa 205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  80. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  81. CONDOMINIUM
    Hale Ono Loa 402

    Hale Ono Loa 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $331/night

  82. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $974/night

  83. CONDOMINIUM
    Hale Ono Loa 416

    Hale Ono Loa 416

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $144 to $306/night

  84. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $548 to $2,016/night

  85. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,668/night

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

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,668/night

  87. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    Kapolei, HI

    Pool Hot Tub

    $443 to $1,384/night

  88. CONDOMINIUM
    Haleakala Shores #B-309

    Haleakala Shores #B-309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $331/night

  89. CONDOMINIUM
    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $617/night

  90. CONDOMINIUM
    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $220 to $238/night

  91. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Pool
    FREE CANCELLATION

    $520 to $581/night

  92. CONDOMINIUM
    Hanalei Bay Resort 5202

    Hanalei Bay Resort 5202

    Princeville, HI

    Pool
    FREE CANCELLATION

    $361 to $410/night

  93. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  94. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  95. CONDOMINIUM
    HBR1207-08

    HBR1207-08

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $405/night

  96. CONDOMINIUM
    Hear the Waves!! Honua Kai- Hokulani 306

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    Pool Hot Tub

    $394 to $1,512/night

  97. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $264/night

  98. CONDOMINIUM
    HOL #216

    HOL #216

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $159 to $348/night

  99. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $289 to $502/night

  100. CONDOMINIUM
    HOL 311

    HOL 311

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $348/night