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 #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  2. HOUSE
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  3. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  4. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  5. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  6. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  7. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  8. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $358 to $1,092/night

  9. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $996 to $3,149/night

  10. VILLA
    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $934 to $2,945/night

  11. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Pool Hot Tub

    $977 to $3,081/night

  12. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,077 to $3,318/night

  13. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,605/night

  14. VILLA
    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    Kamuela, HI

    Pool Hot Tub

    $737 to $2,171/night

  15. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,160 to $3,417/night

  16. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  17. 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 $469/night

  18. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  19. CONDOMINIUM
    Aina Nalu A104

    Aina Nalu A104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $169 to $499/night

  20. CONDOMINIUM
    Aina Nalu B204

    Aina Nalu B204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $564/night

  21. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  22. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $383/night

  23. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION
  24. CONDOMINIUM
    Aina Nalu G204

    Aina Nalu G204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $431/night

  25. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $435/night

  26. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $239/night

  27. CONDOMINIUM
    Aina Nalu K102

    Aina Nalu K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $403/night

  28. CONDOMINIUM
    Aloha Surf 207

    Aloha Surf 207

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $99 to $129/night

  29. CONDOMINIUM
    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $96 to $359/night

  30. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  31. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,031/night

  32. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  33. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  34. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $366 to $501/night

  35. CONDOMINIUM
    Bay Villa 38G2

    Bay Villa 38G2

    Lahaina, HI

    Pool

    $248 to $304/night

  36. CONDOMINIUM
    Bay Villa 38G3

    Bay Villa 38G3

    Lahaina, HI

    Pool

    $248 to $304/night

  37. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  38. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $309 to $326/night

  39. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $186 to $239/night

  40. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $337/night

  41. CONDOMINIUM
    Casa De Emdeko 219

    Casa De Emdeko 219

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  42. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  43. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  44. CONDOMINIUM
    Casa De Emdeko 332

    Casa De Emdeko 332

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  45. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  46. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  47. CONDOMINIUM
    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $242 to $309/night

  48. CONDOMINIUM
    Diamond Head Beach Hotel 501

    Diamond Head Beach Hotel 501

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $315 to $495/night

  49. CONDOMINIUM
    Diamond Head Beach Hotel 601

    Diamond Head Beach Hotel 601

    Honolulu, HI

    FREE CANCELLATION

    $298 to $444/night

  50. CONDOMINIUM
    Diamond Head Beach Hotel 602

    Diamond Head Beach Hotel 602

    Honolulu, HI

    FREE CANCELLATION

    $186 to $309/night

  51. CONDOMINIUM
    Eldorado A203

    Eldorado A203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $479/night

  52. CONDOMINIUM
    Eldorado E104

    Eldorado E104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $433/night

  53. CONDOMINIUM
    Eldorado G205

    Eldorado G205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $556/night

  54. CONDOMINIUM
    Eldorado H107

    Eldorado H107

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $629/night

  55. CONDOMINIUM
    Eldorado J109

    Eldorado J109

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $299/night

  56. CONDOMINIUM
    Eldorado J110

    Eldorado J110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $158 to $349/night

  57. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  58. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $446/night

  59. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $416/night

  60. CONDOMINIUM
    Eldorado K203

    Eldorado K203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $500/night

  61. CONDOMINIUM
    Eldorado L102

    Eldorado L102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $406/night

  62. CONDOMINIUM
    Emmalani Court #525

    Emmalani Court #525

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  63. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  64. CONDOMINIUM
    Golf Villa 19T4

    Golf Villa 19T4

    Lahaina, HI

    Pool

    $197 to $248/night

  65. CONDOMINIUM
    Grand Champions 124

    Grand Champions 124

    Kihei, HI

    Pool
    FREE CANCELLATION

    $269 to $594/night

  66. CONDOMINIUM
    Hale 'Olu'Olu

    Hale 'Olu'Olu

    Waikoloa, HI

    Pool

    $238 to $478/night

  67. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

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

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

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

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

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

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,383/night

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

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $513 to $977/night

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

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $432 to $1,499/night

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

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,209/night

  74. 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

  75. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  76. 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

  77. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $275/night

  78. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  79. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  80. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

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

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,673/night

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

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  83. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,157 to $1,536/night

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

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,093/night

  85. 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

  86. 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

  87. CONDOMINIUM
    Hale Mahina A-403

    Hale Mahina A-403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $234 to $521/night

  88. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  89. 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

  90. 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

  91. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $330/night

  92. CONDOMINIUM
    Hale Mali'e

    Hale Mali'e

    Waikoloa, HI

    Pool

    $294 to $598/night

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

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

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

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,209/night

  95. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  96. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Pool Hot Tub

    $286 to $478/night

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

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,789/night

  98. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  99. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $149 to $454/night

  100. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $331/night