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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  2. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  3. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  4. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    FREE CANCELLATION

    $304 to $467/night

  5. CONDOMINIUM
    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  6. CONDOMINIUM
    C1-2 Bedroom Oceanfront

    C1-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  7. CONDOMINIUM
    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  8. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  9. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  10. CONDOMINIUM
    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  11. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  12. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  13. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  14. CONDOMINIUM
    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  15. CONDOMINIUM
    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  16. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  17. CONDOMINIUM
    Eldorado E104

    Eldorado E104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $479/night

  18. CONDOMINIUM
    Eldorado J110

    Eldorado J110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $138 to $438/night

  19. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $740/night

  20. CONDOMINIUM
    Eldorado K104

    Eldorado K104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $776/night

  21. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  22. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  23. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  24. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  25. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  26. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  27. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  28. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  29. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $1,191/night

  30. CONDOMINIUM
    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $194 to $238/night

  31. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  32. CONDOMINIUM
    Hanalei Bay Resort 5202

    Hanalei Bay Resort 5202

    Princeville, HI

    Pool
    FREE CANCELLATION

    $243 to $410/night

  33. CONDOMINIUM
    Honua Kai 1024

    Honua Kai 1024

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $520/night

  34. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $445/night

  35. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $464/night

  36. CONDOMINIUM
    Islander on the Beach 259

    Islander on the Beach 259

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $145 to $170/night

  37. 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

  38. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $1,016/night

  39. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $220 to $1,178/night

  40. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  41. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $501/night

  42. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $163 to $435/night

  43. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $154 to $381/night

  44. CONDOMINIUM
    Kahana Reef 303

    Kahana Reef 303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $129 to $336/night

  45. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $411/night

  46. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $461/night

  47. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $169 to $548/night

  48. CONDOMINIUM
    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $1,000/night

  49. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $471/night

  50. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $464/night

  51. CONDOMINIUM
    Ke Nani Kai Condo 113

    Ke Nani Kai Condo 113

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $169/night

  52. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-104

    Keauhou Kona Surf & Racquet Club #5-104

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $453 to $467/night

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

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $314 to $326/night

  54. CONDOMINIUM
    Kepuhi Beach 1226

    Kepuhi Beach 1226

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $135/night

  55. CONDOMINIUM
    Kulakane 301

    Kulakane 301

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $225 to $708/night

  56. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  57. CONDOMINIUM
    Kulakane 306

    Kulakane 306

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  58. CONDOMINIUM
    Kulakane 307

    Kulakane 307

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $531/night

  59. CONDOMINIUM
    Kuleana 313

    Kuleana 313

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $211 to $636/night

  60. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $596/night

  61. CONDOMINIUM
    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $747/night

  62. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $804/night

  63. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $241 to $749/night

  64. CONDOMINIUM
    Mahana 1008

    Mahana 1008

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $266 to $1,105/night

  65. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $869/night

  66. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $1,245/night

  67. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $724/night

  68. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $499/night

  69. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $298/night

  70. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469/night

  71. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $250 to $625/night

  72. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $581/night

  73. CONDOMINIUM
    Napili Shores C116

    Napili Shores C116

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $249/night

  74. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $311/night

  75. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $799/night

  76. CONDOMINIUM
    Paniolo Hale Condo C1

    Paniolo Hale Condo C1

    Maunaloa, HI

    Pool
    FREE CANCELLATION

    $152/night

  77. CONDOMINIUM
    Paniolo Hale R2

    Paniolo Hale R2

    Maunaloa, HI

    Pool
    FREE CANCELLATION

    $169/night

  78. COTTAGE
    Pukoo Cottage (1-Bedroom Cottage)

    Pukoo Cottage (1-Bedroom Cottage)

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $338/night

  79. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $498/night

  80. CONDOMINIUM
    Royal Kahana 802

    Royal Kahana 802

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $569/night

  81. CONDOMINIUM
    Sands of Kahana 354

    Sands of Kahana 354

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,185/night

  82. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $320 to $741/night

  83. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $320 to $901/night

  84. CONDOMINIUM
    Wailea Ekahi 36C

    Wailea Ekahi 36C

    Wailea, HI

    Pool
    FREE CANCELLATION

    $419/night

  85. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    Pool
    FREE CANCELLATION

    $182 to $257/night

  86. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $720/night