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 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $364 to $1,219/night

  2. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $283 to $1,063/night

  3. CONDOMINIUM
    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $617/night

  4. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  5. CONDOMINIUM
    Maui Kamaole #G-210

    Maui Kamaole #G-210

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $377 to $493/night

  6. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  7. CONDOMINIUM
    Palm Leaf

    Palm Leaf

    Kamuela, HI

    Pool Hot Tub

    $238 to $598/night

  8. CONDOMINIUM
    Kamaole Sands #5-414

    Kamaole Sands #5-414

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $429/night

  9. CONDOMINIUM
    Maui Kamaole #J-103

    Maui Kamaole #J-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $342/night

  10. CONDOMINIUM
    Kihei Bay Vista #A-201

    Kihei Bay Vista #A-201

    Kihei, HI

    Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  11. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  12. CONDOMINIUM
    Kihei Bay Surf #213

    Kihei Bay Surf #213

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  13. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,174/night

  14. CONDOMINIUM
    Kihei Bay Surf #109

    Kihei Bay Surf #109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  15. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool Hot Tub

    $456 to $659/night

  16. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool Hot Tub

    $299 to $452/night

  17. CONDOMINIUM
    Maui Kamaole #M-105

    Maui Kamaole #M-105

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $339/night

  18. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  19. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  20. CONDOMINIUM
    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $186/night

  21. CONDOMINIUM
    Maui Kamaole #J-217

    Maui Kamaole #J-217

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $371/night

  22. CONDOMINIUM
    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    Kapaa, HI

    Pool Hot Tub

    $334 to $553/night

  23. CONDOMINIUM
    Pali Ke Kua #118

    Pali Ke Kua #118

    Princeville, HI

    Pool Hot Tub

    $247 to $282/night

  24. CONDOMINIUM
    Kihei Bay Surf #208

    Kihei Bay Surf #208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  25. CONDOMINIUM
    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    Kapaa, HI

    Pool Hot Tub

    $282 to $535/night

  26. CONDOMINIUM
    Kihei Bay Surf #110

    Kihei Bay Surf #110

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $158 to $297/night

  27. CONDOMINIUM
    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    Koloa, HI

    Pool Hot Tub

    $289 to $394/night

  28. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $608 to $846/night

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

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $397 to $977/night

  30. CONDOMINIUM
    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  31. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $383/night

  32. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $521/night

  33. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $213 to $365/night

  34. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $270 to $458/night

  35. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $610/night

  36. CONDOMINIUM
    Kamaole Sands #7-305

    Kamaole Sands #7-305

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $434/night

  37. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $227 to $393/night

  38. CONDOMINIUM
    Palms at Wailea #604

    Palms at Wailea #604

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $288 to $450/night

  39. CONDOMINIUM
    Kamaole Sands #9-203

    Kamaole Sands #9-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $208/night

  40. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $413/night

  41. CONDOMINIUM
    Maui Kamaole #A-201

    Maui Kamaole #A-201

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $328 to $570/night

  42. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $414/night

  43. 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 $269/night

  44. CONDOMINIUM
    Fairway Villas #K1 at the Waikoloa Beach Resort

    Fairway Villas #K1 at the Waikoloa Beach Resort

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $706/night

  45. CONDOMINIUM
    Kanaloa At Kona #3701

    Kanaloa At Kona #3701

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $163 to $649/night

  46. CONDOMINIUM
    White Sands Village #135

    White Sands Village #135

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $375/night

  47. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  48. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  49. CONDOMINIUM
    Kamaole Sands #2-306

    Kamaole Sands #2-306

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $347/night

  50. TOWNHOUSE
    THE SHORES OF MAUI #223

    THE SHORES OF MAUI #223

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $438/night

  51. CONDOMINIUM
    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $625 to $1,653/night

  52. CONDOMINIUM
    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $451/night

  53. CONDOMINIUM
    Kamaole Sands #4-105

    Kamaole Sands #4-105

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $371/night

  54. CONDOMINIUM
    Kamaole Sands #8-208

    Kamaole Sands #8-208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $289/night

  55. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  56. CONDOMINIUM
    Maalaea Banyans #403

    Maalaea Banyans #403

    Maalaea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $371/night

  57. CONDOMINIUM
    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    Kapaa, HI

    Pool Hot Tub

    $340 to $503/night

  58. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  59. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

  60. CONDOMINIUM
    Kihei Garden Estates #H-203

    Kihei Garden Estates #H-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $335/night

  61. CONDOMINIUM
    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    Koloa, HI

    Pool Hot Tub

    $363 to $528/night

  62. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool Hot Tub

    $270 to $338/night

  63. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $227 to $339/night

  64. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  65. CONDOMINIUM
    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $138 to $231/night

  66. CONDOMINIUM
    Maui Kamaole #D-107

    Maui Kamaole #D-107

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $238/night

  67. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $169/night

  68. CONDOMINIUM
    Kihei Garden Estates #E-204

    Kihei Garden Estates #E-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $244/night

  69. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $365/night

  70. CONDOMINIUM
    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $431/night

  71. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  72. CONDOMINIUM
    White Sands Village #206

    White Sands Village #206

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $141 to $453/night

  73. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $391/night

  74. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $413/night

  75. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  76. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  77. HOUSE
    Beautiful Resort! Close to Beaches! Pool & Hot Tub! Fairway Villas Unit N-3

    Beautiful Resort! Close to Beaches! Pool & Hot Tub! ...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $303/night

  78. CONDOMINIUM
    Exceptional Value for Family! Beautiful Views, Sunsets & Minutes from the Beach!

    Exceptional Value for Family! Beautiful Views, Sunsets &...

    Waikoloa Village, HI

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $286/night

  79. CONDOMINIUM
    Shores at Waikoloa #234 at Bo Tree Tower

    Shores at Waikoloa #234 at Bo Tree Tower

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $464/night

  80. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  81. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  82. CONDOMINIUM
    no image

    Maui Kamaole #H-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $383/night

  83. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $901/night

  84. CONDOMINIUM
    Kihei Bay Vista #D-202

    Kihei Bay Vista #D-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  85. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  86. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  87. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $319 to $447/night

  88. CONDOMINIUM
    Kihei Bay Vista #C-108

    Kihei Bay Vista #C-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  89. CONDOMINIUM
    The Mauna Lani Golf Villas K5

    The Mauna Lani Golf Villas K5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  90. CONDOMINIUM
    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $293 to $770/night

  91. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool Hot Tub

    $259 to $361/night

  92. CONDOMINIUM
    Kihei Bay Surf #144

    Kihei Bay Surf #144

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $110 to $168/night

  93. CONDOMINIUM
    New Listing! Ocean-View Apartment w/ Pool & Spa

    New Listing! Ocean-View Apartment w/ Pool & Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $306/night

  94. CONDOMINIUM
    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    Kapaa, HI

    Pool Hot Tub

    $322 to $423/night

  95. CONDOMINIUM
    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    Koloa, HI

    Pool Hot Tub

    $392 to $514/night

  96. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  97. CONDOMINIUM
    Kihei Garden Estates #A-102

    Kihei Garden Estates #A-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $196/night

  98. CONDOMINIUM
    Surfs Up

    Surfs Up

    Waikoloa, HI

    Pool Hot Tub

    $286 to $586/night

  99. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  100. CONDOMINIUM
    Waikoloa Beach Villas O2

    Waikoloa Beach Villas O2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $478/night