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
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    Pool

    $594 to $1,063/night

  2. CONDOMINIUM
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  3. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  4. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  5. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  6. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  7. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  8. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  9. CONDOMINIUM
    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $431/night

  10. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  11. CONDOMINIUM
    Kaleialoha #207

    Kaleialoha #207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  12. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  13. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $477/night

  14. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $459/night

  15. CONDOMINIUM
    Royal Kahana 1012

    Royal Kahana 1012

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $551/night

  16. CONDOMINIUM
    Royal Kahana 702

    Royal Kahana 702

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $346/night

  17. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $289 to $502/night

  18. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  19. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  20. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  21. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  22. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $625/night

  23. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  24. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  25. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  26. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  27. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  28. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  29. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $990/night

  30. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  31. CONDOMINIUM
    Kaleialoha #214

    Kaleialoha #214

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  32. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  33. CONDOMINIUM
    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b/1b

    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b...

    Kaanapali, HI

    Pool Hot Tub

    $257 to $912/night

  34. CONDOMINIUM
    Honua Kai- Hokulani 930- View of the Rainbow Mountains! 1b/1b

    Honua Kai- Hokulani 930- View of the Rainbow Mountains! ...

    Kaanapali, HI

    Pool Hot Tub

    $246 to $977/night

  35. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  36. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  37. CONDOMINIUM
    Lauloa 105

    Lauloa 105

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $236 to $438/night

  38. CONDOMINIUM
    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $338 to $750/night

  39. CONDOMINIUM
    Kaleialoha 211

    Kaleialoha 211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $375/night

  40. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $303/night

  41. CONDOMINIUM
    Honua Kai 1024

    Honua Kai 1024

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $440/night

  42. CONDOMINIUM
    Mahana 1113

    Mahana 1113

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $981/night

  43. CONDOMINIUM
    Mahana 602

    Mahana 602

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $715/night

  44. CONDOMINIUM
    Maui Kai 201

    Maui Kai 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $873/night

  45. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $425 to $749/night

  46. CONDOMINIUM
    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $474 to $810/night

  47. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $345/night

  48. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $186 to $310/night

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

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  50. HOUSE
    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    Wailea, Maui, HI

    Pool

    $841 to $1,515/night

  51. 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

  52. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  53. CONDOMINIUM
    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua, HI

    Pool

    $494 to $781/night

  54. 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

  55. CONDOMINIUM
    Ilikai #1743

    Ilikai #1743

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $404 to $619/night

  56. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  57. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $302 to $326/night

  58. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  59. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $454/night

  60. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  61. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $181 to $239/night

  62. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  63. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  64. CONDOMINIUM
    Royal Kahana 107 1Bdrm

    Royal Kahana 107 1Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $346/night

  65. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  66. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  67. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $336/night

  68. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  69. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  70. CONDOMINIUM
    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  71. CONDOMINIUM
    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  72. CONDOMINIUM
    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  73. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  74. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  75. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  76. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $165 to $273/night

  77. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $588/night

  78. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $136 to $261/night

  79. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $469/night

  80. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  81. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  82. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  83. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  84. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  85. CONDOMINIUM
    Kaleialoha #413

    Kaleialoha #413

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  86. CONDOMINIUM
    Kaleialoha #113

    Kaleialoha #113

    LAHAINA, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  87. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  88. CONDOMINIUM
    HOL 311

    HOL 311

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $295/night

  89. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $322 to $1,154/night

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

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    Pool Hot Tub

    $394 to $1,513/night

  91. CONDOMINIUM
    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $376 to $1,513/night

  92. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $283 to $606/night

  93. CONDOMINIUM
    Maui Kai 206

    Maui Kai 206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $438/night

  94. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $211 to $498/night

  95. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $304/night

  96. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $384 to $990/night

  97. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $136 to $415/night

  98. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $361/night

  99. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $220 to $363/night

  100. CONDOMINIUM
    Papakea J107

    Papakea J107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $498/night