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
    Papakea J107

    Papakea J107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $484/night

  2. 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

  3. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Pool
    FREE CANCELLATION

    $137 to $470/night

  4. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $608/night

  5. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  6. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $158 to $239/night

  7. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $463/night

  8. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $149 to $454/night

  9. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $128 to $249/night

  10. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  11. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  12. CONDOMINIUM
    Kuleana 622 1Bdrm

    Kuleana 622 1Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $436/night

  13. CONDOMINIUM
    Maui Kai 605

    Maui Kai 605

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $336/night

  14. CONDOMINIUM
    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $359/night

  15. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  16. CONDOMINIUM
    Leinaala Oceanfront #405

    Leinaala Oceanfront #405

    Kihei, HI

    Pool
    FREE CANCELLATION

    $335 to $582/night

  17. CONDOMINIUM
    Honokeana Cove 103

    Honokeana Cove 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $208 to $336/night

  18. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    FREE CANCELLATION

    $360 to $557/night

  19. APARTMENT
    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $124 to $174/night

  20. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night

  21. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  22. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  23. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  24. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  25. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $467/night

  26. CONDOMINIUM
    Royal Kahana 1012

    Royal Kahana 1012

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $243 to $433/night

  27. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  28. CONDOMINIUM
    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    Kihei, HI

    Pool
    FREE CANCELLATION

    $139 to $244/night

  29. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $585 to $622/night

  30. CONDOMINIUM
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    Pool

    $594 to $1,063/night

  31. CONDOMINIUM
    Royal Kahana 702

    Royal Kahana 702

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $333/night

  32. CONDOMINIUM
    Kaleialoha #214

    Kaleialoha #214

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $413/night

  33. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $289 to $620/night

  34. CONDOMINIUM
    Maui Sands K1

    Maui Sands K1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $211/night

  35. CONDOMINIUM
    Maalaea Banyans #403

    Maalaea Banyans #403

    Maalaea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $371/night

  36. CONDOMINIUM
    Hale Ono Loa 102

    Hale Ono Loa 102

    lahaina, HI

    Pool
    FREE CANCELLATION

    $139 to $456/night

  37. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  38. 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 $989/night

  39. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $177 to $357/night

  40. CONDOMINIUM
    Kaleialoha 211

    Kaleialoha 211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $375/night

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

    Keauhou Kona Surf & Racket Club Townhouse #4

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $389 to $428/night

  42. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  43. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $361 to $749/night

  44. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $345/night

  45. CONDOMINIUM
    Alii Kai 3103

    Alii Kai 3103

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $293/night

  46. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  47. CONDOMINIUM
    Kanaloa At Kona #3001

    Kanaloa At Kona #3001

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $579/night

  48. CONDOMINIUM
    Sea Village #3318

    Sea Village #3318

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $125 to $480/night

  49. CONDOMINIUM
    Kona Nalu #302

    Kona Nalu #302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $574/night

  50. CONDOMINIUM
    Kanaloa At Kona #3701

    Kanaloa At Kona #3701

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $163 to $649/night

  51. CONDOMINIUM
    Alii Villas #132

    Alii Villas #132

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $135 to $434/night

  52. CONDOMINIUM
    Sea Village #4114

    Sea Village #4114

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $225 to $776/night

  53. CONDOMINIUM
    Kona Bali Kai #206- 2 Bedroom

    Kona Bali Kai #206- 2 Bedroom

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $536/night

  54. CONDOMINIUM
    Country Club Villas #208

    Country Club Villas #208

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $480/night

  55. CONDOMINIUM
    Kona Reef #D31

    Kona Reef #D31

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $734/night

  56. HOUSE
    Nai'a Hale

    Nai'a Hale

    Kailua Kona, HI

    FREE CANCELLATION

    $719 to $1,411/night

  57. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  58. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  59. CONDOMINIUM
    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $269/night

  60. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  61. 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

  62. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $348 to $451/night

  63. CONDOMINIUM
    Mahana 519

    Mahana 519

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $410 to $1,336/night

  64. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  65. CONDOMINIUM
    Sealodge J1

    Sealodge J1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  66. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club #176

    Keauhou Kona Surf & Racquet Club #176

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $358/night

  67. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  68. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  69. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  70. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $813/night

  71. CONDOMINIUM
    Honua Kai 1024

    Honua Kai 1024

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $416/night

  72. CONDOMINIUM
    Maui Kai 506

    Maui Kai 506

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $724/night

  73. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $227 to $340/night

  74. CONDOMINIUM
    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $431/night

  75. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  76. CONDOMINIUM
    Kona Reef D32

    Kona Reef D32

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $292/night

  77. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $264/night

  78. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  79. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  80. CONDOMINIUM
    Sealodge J9

    Sealodge J9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  81. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $238 to $257/night

  82. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $625/night

  83. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $389/night

  84. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  85. CONDOMINIUM
    Kahana Sunset A5

    Kahana Sunset A5

    Lahaina, HI

    Pool

    $428 to $484/night

  86. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  87. CONDOMINIUM
    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $499/night

  88. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  89. CONDOMINIUM
    Kahana Villa F410

    Kahana Villa F410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $353/night

  90. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $363/night

  91. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  92. CONDOMINIUM
    Kaleialoha 402

    Kaleialoha 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $129 to $294/night

  93. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $296/night

  94. 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

  95. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $413/night

  96. HOUSE
    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  97. CONDOMINIUM
    Hale Kania Kai at Surf & Racquet 3302

    Hale Kania Kai at Surf & Racquet 3302

    Kailua-Kona,, HI

    Pool
    FREE CANCELLATION

    $279 to $401/night

  98. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  99. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  100. CONDOMINIUM
    Valley Isle 204

    Valley Isle 204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $363/night