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
    Royal Kahana 802

    Royal Kahana 802

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $569/night

  2. HOUSE
    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    Makena, Maui, HI

    Pool

    $775 to $1,094/night

  3. HOUSE
    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    Kihei, Maui, HI

    Hot Tub

    $1,234 to $2,694/night

  4. HOUSE
    SUGAR BEACH RESORT, #524^

    SUGAR BEACH RESORT, #524^

    Kihei, Maui, HI

    Pool

    $190 to $387/night

  5. HOUSE
    MENEHUNE SHORES, #623**

    MENEHUNE SHORES, #623**

    Kihei, Maui, HI

    Pool

    $201 to $336/night

  6. HOUSE
    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    Makena, Maui, HI

    Pool

    $583 to $926/night

  7. HOUSE
    ROYAL MAUIAN, #302

    ROYAL MAUIAN, #302

    Kihei, Maui, HI

    Pool

    $560 to $702/night

  8. HOUSE
    KIHEI BEACH, #309

    KIHEI BEACH, #309

    Kihei, Maui, HI

    $263 to $421/night

  9. HOUSE
    SUGAR BEACH RESORT, #418

    SUGAR BEACH RESORT, #418

    Kihei, Maui, HI

    Pool

    $202 to $387/night

  10. HOUSE
    WAILEA EKAHI, #22D

    WAILEA EKAHI, #22D

    Wailea, Maui, HI

    Pool

    $336 to $432/night

  11. CONDOMINIUM
    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    Wailea, Maui, HI

    Pool

    $931 to $1,459/night

  12. CONDOMINIUM
    ROYAL MAUIAN, #403

    ROYAL MAUIAN, #403

    Kihei, Maui, HI

    Pool

    $336 to $505/night

  13. HOUSE
    KAMAOLE NALU, #604^

    KAMAOLE NALU, #604^

    Kihei, Maui, HI

    $247 to $459/night

  14. CONDOMINIUM
    Menehune Shores, #422

    Menehune Shores, #422

    Kihei, HI

    Pool

    $246 to $336/night

  15. CONDOMINIUM
    KIHEI SURFSIDE, #511

    KIHEI SURFSIDE, #511

    Kihei, Maui, HI

    Pool

    $190 to $448/night

  16. CONDOMINIUM
    ROYAL MAUIAN, #614

    ROYAL MAUIAN, #614

    Kihei, Maui, HI

    $425 to $561/night

  17. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $668 to $846/night

  18. CONDOMINIUM
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  19. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  20. CONDOMINIUM
    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  21. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  22. CONDOMINIUM
    Maui Sands K1

    Maui Sands K1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $211/night

  23. CONDOMINIUM
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    Pool

    $428 to $484/night

  24. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  25. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  26. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  27. CONDOMINIUM
    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    Kihei, HI

    Pool
    FREE CANCELLATION

    $139 to $244/night

  28. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  29. CONDOMINIUM
    Valley Isle 204

    Valley Isle 204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $363/night

  30. CONDOMINIUM
    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $269/night

  31. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $219/night

  32. CONDOMINIUM
    Kaleialoha 402

    Kaleialoha 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $379/night

  33. CONDOMINIUM
    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $431/night

  34. CONDOMINIUM
    Sugar Beach #133

    Sugar Beach #133

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $318 to $426/night

  35. CONDOMINIUM
    Kahana Reef #101

    Kahana Reef #101

    LAHAINA, HI

    Pool
    FREE CANCELLATION

    $276 to $326/night

  36. CONDOMINIUM
    Kihei Surfside #210

    Kihei Surfside #210

    KIHEI, HI

    Pool
    FREE CANCELLATION

    $344 to $460/night

  37. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  38. CONDOMINIUM
    Kahana Reef #313

    Kahana Reef #313

    LAHAINA, HI

    Pool
    FREE CANCELLATION

    $290 to $563/night

  39. CONDOMINIUM
    Sugar Beach #317

    Sugar Beach #317

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  40. CONDOMINIUM
    Sugar Beach #132

    Sugar Beach #132

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $334 to $444/night

  41. CONDOMINIUM
    Kaleialoha #207

    Kaleialoha #207

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  42. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  43. CONDOMINIUM
    Sugar Beach #227

    Sugar Beach #227

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $318 to $426/night

  44. CONDOMINIUM
    Menehune Shores #425

    Menehune Shores #425

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  45. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  46. CONDOMINIUM
    Kahana Reef #207

    Kahana Reef #207

    LAHAINA, HI

    Pool
    FREE CANCELLATION

    $290 to $341/night

  47. CONDOMINIUM
    Kihei Surfside #412

    Kihei Surfside #412

    KIHEI, HI

    Pool
    FREE CANCELLATION

    $344 to $460/night

  48. CONDOMINIUM
    Maalaea Banyans #403

    Maalaea Banyans #403

    Maalaea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $371/night

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

    Keauhou Kona Surf & Racquet Club #3-203

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $354 to $409/night

  50. CONDOMINIUM
    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $279 to $401/night

  51. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $409/night

  52. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  53. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $296/night

  54. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $255 to $610/night

  55. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $477/night

  56. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $459/night

  57. CONDOMINIUM
    Kona Reef D32

    Kona Reef D32

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $292/night

  58. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #3-101 "Hale Malama Pono"

    Keauhou Kona Surf & Racquet Club #3-101 "Hale M...

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $292 to $350/night

  59. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $343 to $452/night

  60. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $421/night

  61. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $585 to $626/night

  62. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club #176

    Keauhou Kona Surf & Racquet Club #176

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $325 to $360/night

  63. CONDOMINIUM
    Royal Kahana 1012

    Royal Kahana 1012

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $551/night

  64. CONDOMINIUM
    Royal Kahana 702

    Royal Kahana 702

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $346/night

  65. CONDOMINIUM
    Hale Ono Loa 102

    Hale Ono Loa 102

    lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $456/night

  66. CONDOMINIUM
    Leinaala Oceanfront #302

    Leinaala Oceanfront #302

    Kihei, HI

    Pool
    FREE CANCELLATION

    $161 to $278/night

  67. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $289 to $502/night

  68. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  69. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  70. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  71. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  72. CONDOMINIUM
    Kahana Villa F410

    Kahana Villa F410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $206 to $353/night

  73. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  74. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  75. CONDOMINIUM
    Kaleialoha 112

    Kaleialoha 112

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $167 to $381/night

  76. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $625/night

  77. CONDOMINIUM
    Kahana Reef 111

    Kahana Reef 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $415/night

  78. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  79. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  80. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night

  81. CONDOMINIUM
    Kahana Sunset A5

    Kahana Sunset A5

    Lahaina, HI

    Pool

    $428 to $484/night

  82. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  83. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  84. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  85. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  86. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  87. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #4

    Keauhou Kona Surf & Racket Club Townhouse #4

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $389 to $430/night

  88. 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

  89. CONDOMINIUM
    Hanalei Colony G1

    Hanalei Colony G1

    Haena, HI

    FREE CANCELLATION

    $374 to $499/night

  90. CONDOMINIUM
    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $335 to $390/night

  91. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  92. CONDOMINIUM
    Kaleialoha #214

    Kaleialoha #214

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  93. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  94. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  95. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  96. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $238 to $257/night

  97. CONDOMINIUM
    Sealodge J9

    Sealodge J9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  98. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Pool
    FREE CANCELLATION

    $257 to $361/night

  99. CONDOMINIUM
    Alii Kai 3103

    Alii Kai 3103

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $293/night

  100. 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