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
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  2. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  3. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  4. CONDOMINIUM
    Ke Nani Kai 237

    Ke Nani Kai 237

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $152 to $197/night

  5. HOUSE
    Hale Hiamoe

    Hale Hiamoe

    Kaunakakai, HI

    FREE CANCELLATION

    $225 to $338/night

  6. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  7. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  8. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  9. CONDOMINIUM
    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $363/night

  10. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  11. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  12. 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

  13. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  14. CONDOMINIUM
    Kihei Bay Surf #123

    Kihei Bay Surf #123

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  15. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $573 to $1,344/night

  16. HOUSE
    A Ala Hale

    A Ala Hale

    Kaunakakai, HI

    FREE CANCELLATION

    $225 to $309/night

  17. CONDOMINIUM
    128

    128

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  18. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  19. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $488/night

  20. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  21. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  22. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  23. CONDOMINIUM
    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  24. CONDOMINIUM
    Kihei Bay Vista #D-208

    Kihei Bay Vista #D-208

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $219/night

  25. CONDOMINIUM
    Wailea Ekolu #911

    Wailea Ekolu #911

    Wailea, HI

    Pool
    FREE CANCELLATION

    $231 to $347/night

  26. CONDOMINIUM
    Wailea Ekolu #407

    Wailea Ekolu #407

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $347/night

  27. CONDOMINIUM
    Maui Kamaole #F-210

    Maui Kamaole #F-210

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $360/night

  28. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  29. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  30. CONDOMINIUM
    Pacific Shores #A-101

    Pacific Shores #A-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $158 to $244/night

  31. CONDOMINIUM
    Pali Ke Kua #103

    Pali Ke Kua #103

    Princeville, HI

    Pool Hot Tub

    $354 to $456/night

  32. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $604/night

  33. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  34. CONDOMINIUM
    Kihei Bay Surf #253

    Kihei Bay Surf #253

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  35. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  36. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  37. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $614/night

  38. CONDOMINIUM
    Shores of Maui #211

    Shores of Maui #211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $335/night

  39. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  40. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $347/night

  41. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  42. CONDOMINIUM
    117

    117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  43. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  44. CONDOMINIUM
    236

    236

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  45. CONDOMINIUM
    133

    133

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  46. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  47. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  48. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $148 to $183/night

  49. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $209/night

  50. CONDOMINIUM
    205

    205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  51. CONDOMINIUM
    Keawakapu Views #206

    Keawakapu Views #206

    Kihei, HI

    FREE CANCELLATION

    $157 to $261/night

  52. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  53. HOUSE
    Moloa'a Bay Villa

    Moloa'a Bay Villa

    Anahola, HI

    $1,208 to $1,413/night

  54. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  55. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  56. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  57. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  58. CONDOMINIUM
    Menehune Shores #401

    Menehune Shores #401

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  59. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  60. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  61. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  62. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $351 to $384/night

  63. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $463/night

  64. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $337/night

  65. CONDOMINIUM
    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $409/night

  66. CONDOMINIUM
    Alii Villas 340

    Alii Villas 340

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $273 to $292/night

  67. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  68. CONDOMINIUM
    Kona Isle E23

    Kona Isle E23

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $198 to $326/night

  69. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $641 to $934/night

  70. CONDOMINIUM
    Kona Magic Sands 313

    Kona Magic Sands 313

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $312/night

  71. CONDOMINIUM
    Kona Isle D4

    Kona Isle D4

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $224 to $326/night

  72. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $413/night

  73. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $443/night

  74. CONDOMINIUM
    Maui Sunset #B-106

    Maui Sunset #B-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $303/night

  75. CONDOMINIUM
    Leinaala Oceanfront #405

    Leinaala Oceanfront #405

    Kihei, HI

    Pool
    FREE CANCELLATION

    $342 to $588/night

  76. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $380 to $653/night

  77. CONDOMINIUM
    Leinaala Oceanfront #301

    Leinaala Oceanfront #301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $230 to $422/night

  78. CONDOMINIUM
    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    Kihei, HI

    Pool
    FREE CANCELLATION

    $226 to $392/night

  79. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $406 to $697/night

  80. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $259 to $458/night

  81. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $737 to $1,720/night

  82. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $349/night

  83. CONDOMINIUM
    Waiohuli Beach Hale #C-112

    Waiohuli Beach Hale #C-112

    Kihei, HI

    Pool
    FREE CANCELLATION

    $254 to $436/night

  84. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $412/night

  85. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  86. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  87. CONDOMINIUM
    Pali Ke Kua #241

    Pali Ke Kua #241

    Princeville, HI

    Pool Hot Tub

    $241 to $333/night

  88. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $610/night

  89. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $291/night

  90. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  91. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $221/night

  92. CONDOMINIUM
    Casa De Emdeko 332

    Casa De Emdeko 332

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  93. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  94. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  95. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  96. 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

  97. CONDOMINIUM
    Wavecrest C205

    Wavecrest C205

    Ualapue, HI

    FREE CANCELLATION

    $113 to $152/night

  98. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  99. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  100. CONDOMINIUM
    Cottage 2B

    Cottage 2B

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $225 to $281/night