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
    Lahaina Shores 210

    Lahaina Shores 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $145 to $569/night

  2. CONDOMINIUM
    Ka Hale Kaeloha (House of Love) – Romantic Oceanside Condo

    Ka Hale Kaeloha (House of Love) – Romantic Oceanside C...

    Kaunakakai, HI

    Pool Pets OK
    FREE CANCELLATION

    $158 to $191/night

  3. CONDOMINIUM
    Kuleana 313

    Kuleana 313

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $236 to $636/night

  4. CONDOMINIUM
    Maui Kai 1005

    Maui Kai 1005

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $508/night

  5. CONDOMINIUM
    Sealodge G4

    Sealodge G4

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  6. CONDOMINIUM
    Waiohuli Beach Hale #B-205

    Waiohuli Beach Hale #B-205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

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

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  8. CONDOMINIUM
    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $293 to $770/night

  9. CONDOMINIUM
    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  10. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  11. CONDOMINIUM
    Napili Bay 204

    Napili Bay 204

    Lahaina, HI

    $158 to $203/night

  12. CONDOMINIUM
    Kahana Sunset A4

    Kahana Sunset A4

    Lahaina, HI

    Pool

    $428 to $484/night

  13. CONDOMINIUM
    Hale Ono Loa 205

    Hale Ono Loa 205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  14. CONDOMINIUM
    Paki Maui 422

    Paki Maui 422

    Lahaina, HI

    Pool Hot Tub

    $354 to $444/night

  15. CONDOMINIUM
    Sands Of Kahana 275

    Sands Of Kahana 275

    Lahaina, HI

    Pool Hot Tub

    $444 to $557/night

  16. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  17. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  18. CONDOMINIUM
    Maalaea Surf Resort #C-3

    Maalaea Surf Resort #C-3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $244 to $418/night

  19. CONDOMINIUM
    Hale Mahina A-403

    Hale Mahina A-403

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $234 to $521/night

  20. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  21. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

  22. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  23. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  24. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $243 to $384/night

  25. CONDOMINIUM
    Kona Isle C28

    Kona Isle C28

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $239 to $243/night

  26. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  27. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  28. CONDOMINIUM
    Kaleialoha 406

    Kaleialoha 406

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $194 to $331/night

  29. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $401/night

  30. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $194 to $331/night

  31. CONDOMINIUM
    Waiohuli Beach Hale #A-203

    Waiohuli Beach Hale #A-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $255/night

  32. CONDOMINIUM
    Kulakane 306

    Kulakane 306

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  33. CONDOMINIUM
    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua, HI

    Pool

    $594 to $969/night

  34. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $781 to $1,219/night

  35. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $484/night

  36. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  37. CONDOMINIUM
    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  38. CONDOMINIUM
    Sands Of Kahana 318

    Sands Of Kahana 318

    Lahaina, HI

    Pool Hot Tub

    $236 to $276/night

  39. HOUSE
    Hale Koaniani

    Hale Koaniani

    Wainiha, HI

    FREE CANCELLATION

    $717 to $904/night

  40. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  41. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  42. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  43. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  44. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  45. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  46. CONDOMINIUM
    Noelani 211- Modern, Upscale Ocean Front Condo

    Noelani 211- Modern, Upscale Ocean Front Condo

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $371/night

  47. CONDOMINIUM
    Hale Kai 208 2bdrm 2bath

    Hale Kai 208 2bdrm 2bath

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $500/night

  48. TOWNHOUSE
    Puamana 25-4

    Puamana 25-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $249/night

  49. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  50. CONDOMINIUM
    Kona Shores#130

    Kona Shores#130

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $198 to $219/night

  51. CONDOMINIUM
    Sea Village 3-317

    Sea Village 3-317

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $245 to $256/night

  52. CONDOMINIUM
    Valley Isle #1104

    Valley Isle #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $375/night

  53. CONDOMINIUM
    Hoyochi Nikko #202

    Hoyochi Nikko #202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $330/night

  54. CONDOMINIUM
    Lahaina Roads 209

    Lahaina Roads 209

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $213 to $438/night

  55. CONDOMINIUM
    Papakea B201

    Papakea B201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $385/night

  56. CONDOMINIUM
    Valley Isle 902

    Valley Isle 902

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $150 to $351/night

  57. CONDOMINIUM
    Waiohuli Beach Hale #D-223

    Waiohuli Beach Hale #D-223

    Kihei, HI

    Pool
    FREE CANCELLATION

    $216 to $370/night

  58. CONDOMINIUM
    Leinaala Oceanfront #105

    Leinaala Oceanfront #105

    Kihei, HI

    Pool
    FREE CANCELLATION

    $264 to $454/night

  59. CONDOMINIUM
    Waiohuli Beach Hale #D-225

    Waiohuli Beach Hale #D-225

    Kihei, HI

    Pool
    FREE CANCELLATION

    $230 to $392/night

  60. HOUSE
    Wilikoki House

    Wilikoki House

    Hanalei, HI

    FREE CANCELLATION

    $1,870 to $2,494/night

  61. CONDOMINIUM
    Sealodge E8

    Sealodge E8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $269/night

  62. CONDOMINIUM
    Kaleialoha #313

    Kaleialoha #313

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  63. CONDOMINIUM
    Napili Point A9

    Napili Point A9

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $339 to $721/night

  64. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $308 to $1,018/night

  65. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $314 to $1,018/night

  66. CONDOMINIUM
    Hale Ono Loa 416

    Hale Ono Loa 416

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $151 to $321/night

  67. CONDOMINIUM
    Royal Kahana 920

    Royal Kahana 920

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $225 to $443/night

  68. CONDOMINIUM
    Hoyochi Nikko 108

    Hoyochi Nikko 108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $409/night

  69. CONDOMINIUM
    Kulakane 211

    Kulakane 211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $133 to $291/night

  70. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $315/night

  71. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $153 to $345/night

  72. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $165 to $293/night

  73. CONDOMINIUM
    Hololani A204

    Hololani A204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $208 to $425/night

  74. CONDOMINIUM
    Kulakane 301

    Kulakane 301

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $245 to $533/night

  75. CONDOMINIUM
    Royal Kahana 308

    Royal Kahana 308

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $415/night

  76. CONDOMINIUM
    Waiohuli Beach Hale #C-111

    Waiohuli Beach Hale #C-111

    Kihei, HI

    Pool
    FREE CANCELLATION

    $232 to $406/night

  77. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  78. CONDOMINIUM
    Sealodge C7

    Sealodge C7

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  79. CONDOMINIUM
    Sealodge G3

    Sealodge G3

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $269/night

  80. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  81. CONDOMINIUM
    Kona Isle #D1

    Kona Isle #D1

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $125 to $474/night

  82. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $338 to $934/night

  83. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $475/night

  84. CONDOMINIUM
    Papakea G301

    Papakea G301

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $270/night

  85. CONDOMINIUM
    Kahana Reef 107

    Kahana Reef 107

    Lahaina, HI

    FREE CANCELLATION

    $133 to $378/night

  86. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $769/night

  87. CONDOMINIUM
    Maalaea Banyans 203

    Maalaea Banyans 203

    Wailuku, HI

    Pool Hot Tub
    FREE CANCELLATION

    $154 to $288/night

  88. CONDOMINIUM
    Napili Point B44

    Napili Point B44

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $239 to $576/night

  89. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $594/night

  90. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $424/night

  91. CONDOMINIUM
    Napili Shores I270

    Napili Shores I270

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $436/night

  92. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $350/night

  93. CONDOMINIUM
    Sealodge E10

    Sealodge E10

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  94. CONDOMINIUM
    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $174 to $431/night

  95. CONDOMINIUM
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $309 to $920/night

  96. CONDOMINIUM
    Kaleialoha #414

    Kaleialoha #414

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $443/night

  97. CONDOMINIUM
    Diamond Head Beach Hotel 1202

    Diamond Head Beach Hotel 1202

    Honolulu, HI

    FREE CANCELLATION

    $248 to $326/night

  98. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $158 to $239/night

  99. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $158 to $191/night

  100. CONDOMINIUM
    Napili Point C-12 2bdrm/2bath

    Napili Point C-12 2bdrm/2bath

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $359 to $616/night