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
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  2. CONDOMINIUM
    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    Lahaina, HI

    FREE CANCELLATION

    $217 to $604/night

  3. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    FREE CANCELLATION

    $360 to $557/night

  4. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

  5. CONDOMINIUM
    Napili Shores F147

    Napili Shores F147

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $236 to $510/night

  6. CONDOMINIUM
    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    Kapaa, HI

    Pool

    $282 to $398/night

  7. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool

    $456 to $543/night

  8. CONDOMINIUM
    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    Kapaa, HI

    Pool

    $340 to $467/night

  9. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool

    $256 to $344/night

  10. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool

    $299 to $415/night

  11. CONDOMINIUM
    Palms Waikiki 720

    Palms Waikiki 720

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $168 to $197/night

  12. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  13. CONDOMINIUM
    Poolside Aina Nalu Condo D107

    Poolside Aina Nalu Condo D107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $661/night

  14. CONDOMINIUM
    Poolside Aina Nalu Condo D109

    Poolside Aina Nalu Condo D109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $661/night

  15. CONDOMINIUM
    Lahaina Condo K106

    Lahaina Condo K106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $166 to $553/night

  16. CONDOMINIUM
    Aina Nalu Premier Platinum Condo K101

    Aina Nalu Premier Platinum Condo K101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  17. CONDOMINIUM
    Lahaina Condo I205

    Lahaina Condo I205

    St. Lahaina, HI

    Pool
    FREE CANCELLATION

    $166 to $553/night

  18. CONDOMINIUM
    Aina Nalu Condo G109

    Aina Nalu Condo G109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  19. CONDOMINIUM
    Maui Ka'anapali Villas Studio Premier Condo A417

    Maui Ka'anapali Villas Studio Premier Condo A417

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $372 to $636/night

  20. CONDOMINIUM
    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lahaina, HI

    FREE CANCELLATION

    $247 to $291/night

  21. CONDOMINIUM
    Aina Nalu Premier Platinum Condo A110

    Aina Nalu Premier Platinum Condo A110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $636/night

  22. CONDOMINIUM
    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  23. CONDOMINIUM
    Maui Parkshore #313

    Maui Parkshore #313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $177 to $354/night

  24. CONDOMINIUM
    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  25. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $409/night

  26. CONDOMINIUM
    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $617/night

  27. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  28. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  29. CONDOMINIUM
    Kihei Garden Estates #H-203

    Kihei Garden Estates #H-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $335/night

  30. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  31. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  32. CONDOMINIUM
    Maui Vista #2-423

    Maui Vista #2-423

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $347/night

  33. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  34. CONDOMINIUM
    Maui Parkshore #212

    Maui Parkshore #212

    Kihei, HI

    Pool
    FREE CANCELLATION

    $179 to $341/night

  35. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  36. CONDOMINIUM
    Kahana Villa F410

    Kahana Villa F410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $206 to $353/night

  37. CONDOMINIUM
    Maalaea Banyans #403

    Maalaea Banyans #403

    Maalaea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $371/night

  38. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  39. CONDOMINIUM
    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  40. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  41. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  42. CONDOMINIUM
    Kona Bali Kai Studio w/ Pool & Spa

    Kona Bali Kai Studio w/ Pool & Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $61 to $231/night

  43. CONDOMINIUM
    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $269/night

  44. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    Kapolei, HI

    Pool Hot Tub
  45. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $365/night

  46. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  47. CONDOMINIUM
    Kihei Akahi #C-203

    Kihei Akahi #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $115 to $242/night

  48. CONDOMINIUM
    Maui Kamaole #J-217

    Maui Kamaole #J-217

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $371/night

  49. CONDOMINIUM
    Kamaole Sands #4-105

    Kamaole Sands #4-105

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $371/night

  50. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  51. CONDOMINIUM
    Palm Leaf

    Palm Leaf

    Kamuela, HI

    Pool Hot Tub

    $238 to $598/night

  52. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  53. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  54. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  55. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $138 to $316/night

  56. CONDOMINIUM
    Maui Vista #2-320

    Maui Vista #2-320

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $289/night

  57. CONDOMINIUM
    Keauhou Gardens #11-101 at Kona Coast Resort

    Keauhou Gardens #11-101 at Kona Coast Resort

    Kailua-Kona, HI

    Pool
    FREE CANCELLATION

    $152 to $206/night

  58. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $668 to $846/night

  59. 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

  60. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  61. HOUSE
    Ali'i Point #5 Oceanfront

    Ali'i Point #5 Oceanfront

    Kailua-Kona, HI

    Pool
    FREE CANCELLATION

    $668 to $846/night

  62. CONDOMINIUM
    Sea Village 3-212

    Sea Village 3-212

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $157 to $242/night

  63. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  64. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    FREE CANCELLATION

    $304 to $467/night

  65. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  66. CONDOMINIUM
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    Pool

    $781 to $1,219/night

  67. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  68. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $296/night

  69. CONDOMINIUM
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $333 to $703/night

  70. CONDOMINIUM
    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $279 to $401/night

  71. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool
  72. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  73. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  74. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  75. CONDOMINIUM
    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $118 to $267/night

  76. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $383/night

  77. CONDOMINIUM
    Maui Kamaole #A-201

    Maui Kamaole #A-201

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $695/night

  78. CONDOMINIUM
    Kihei Bay Surf #109

    Kihei Bay Surf #109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  79. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $322 to $769/night

  80. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $495/night

  81. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $128 to $219/night

  82. CONDOMINIUM
    Kamaole Sands #7-305

    Kamaole Sands #7-305

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $179 to $430/night

  83. CONDOMINIUM
    Palms at Wailea #604

    Palms at Wailea #604

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $466/night

  84. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $637/night

  85. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $470/night

  86. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $559/night

  87. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $255 to $610/night

  88. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $477/night

  89. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  90. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $459/night

  91. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $505/night

  92. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $202 to $480/night

  93. CONDOMINIUM
    Kalani Kai 105

    Kalani Kai 105

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $99 to $428/night

  94. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  95. CONDOMINIUM
    Wailea Ekolu #503

    Wailea Ekolu #503

    Wailea, HI

    Pool
    FREE CANCELLATION

    $232 to $521/night

  96. CONDOMINIUM
    Kihei Bay Vista #A-201

    Kihei Bay Vista #A-201

    Kihei, HI

    Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  97. CONDOMINIUM
    Wailea Ekolu #804

    Wailea Ekolu #804

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $405/night

  98. CONDOMINIUM
    Waiohuli Beach Hale #D-120

    Waiohuli Beach Hale #D-120

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  99. CONDOMINIUM
    Maui Vista #1-418

    Maui Vista #1-418

    Kihei, HI

    Pool
    FREE CANCELLATION

    $173 to $260/night

  100. CONDOMINIUM
    Kamaole Sands #9-203

    Kamaole Sands #9-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $208/night