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
    Diamond Head Beach Hotel 1202

    Diamond Head Beach Hotel 1202

    Honolulu, HI

    FREE CANCELLATION

    $248 to $326/night

  2. CONDOMINIUM
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  3. CONDOMINIUM
    Aina Nalu C108

    Aina Nalu C108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $623/night

  4. CONDOMINIUM
    Aina Nalu C102

    Aina Nalu C102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $623/night

  5. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  6. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  7. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  8. CONDOMINIUM
    International Colony Club #18

    International Colony Club #18

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $566/night

  9. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $266/night

  10. CONDOMINIUM
    Wailea Ekolu #1207

    Wailea Ekolu #1207

    Wailea, HI

    Pool
    FREE CANCELLATION

    $273 to $463/night

  11. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  12. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  13. CONDOMINIUM
    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $118 to $263/night

  14. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $469/night

  15. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $347/night

  16. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  17. CONDOMINIUM
    Maui Kamaole #J-221

    Maui Kamaole #J-221

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $463/night

  18. 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

  19. CONDOMINIUM
    Haleakala Shores #B-309

    Haleakala Shores #B-309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $331/night

  20. CONDOMINIUM
    Nohonani #202

    Nohonani #202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  21. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  22. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $493/night

  23. CONDOMINIUM
    Maui Kamaole #H-211

    Maui Kamaole #H-211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $284 to $405/night

  24. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  25. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  26. CONDOMINIUM
    Wailea Ekahi #45-E

    Wailea Ekahi #45-E

    Wailea, HI

    Pool
    FREE CANCELLATION

    $284 to $435/night

  27. CONDOMINIUM
    Kihei Garden Estates #B-201

    Kihei Garden Estates #B-201

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $226/night

  28. CONDOMINIUM
    Pali Ke Kua #241

    Pali Ke Kua #241

    Princeville, HI

    Pool Hot Tub

    $241 to $333/night

  29. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  30. CONDOMINIUM
    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    Kapaa, HI

    Pool Hot Tub

    $311 to $429/night

  31. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  32. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $413/night

  33. CONDOMINIUM
    Pali Ke Kua #103

    Pali Ke Kua #103

    Princeville, HI

    Pool Hot Tub

    $354 to $456/night

  34. CONDOMINIUM
    Plantations at Princeville #111

    Plantations at Princeville #111

    Princeville, HI

    Pool

    $206 to $340/night

  35. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $347/night

  36. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  37. CONDOMINIUM
    Palms at Wailea #1501

    Palms at Wailea #1501

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $405/night

  38. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  39. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  40. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $148 to $183/night

  41. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  42. CONDOMINIUM
    Puamana 25B

    Puamana 25B

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  43. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $221/night

  44. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  45. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  46. CONDOMINIUM
    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    Kihei, HI

    Pool
    FREE CANCELLATION

    $232 to $394/night

  47. CONDOMINIUM
    Maui Kamaole #A-207

    Maui Kamaole #A-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $348 to $592/night

  48. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $414/night

  49. CONDOMINIUM
    Island Surf #502

    Island Surf #502

    Kihei, HI

    Pool
    FREE CANCELLATION

    $215 to $362/night

  50. CONDOMINIUM
    Palms at Wailea #1102

    Palms at Wailea #1102

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $415 to $702/night

  51. CONDOMINIUM
    Palms at Wailea #2303

    Palms at Wailea #2303

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $390 to $658/night

  52. CONDOMINIUM
    Leinaala Oceanfront #301

    Leinaala Oceanfront #301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $233 to $422/night

  53. CONDOMINIUM
    Maui Kamaole #L-202

    Maui Kamaole #L-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $314 to $527/night

  54. CONDOMINIUM
    Palms at Wailea #205

    Palms at Wailea #205

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $625/night

  55. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  56. CONDOMINIUM
    Waiohuli Beach Hale #B-108

    Waiohuli Beach Hale #B-108

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  57. CONDOMINIUM
    Kihei Alii Kai #D-406

    Kihei Alii Kai #D-406

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $290/night

  58. CONDOMINIUM
    Waiohuli Beach Hale #C-113

    Waiohuli Beach Hale #C-113

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  59. CONDOMINIUM
    Kamaole Sands #1-103

    Kamaole Sands #1-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $278/night

  60. CONDOMINIUM
    Kanai A Nalu #311

    Kanai A Nalu #311

    Maalaea, HI

    Pool
    FREE CANCELLATION

    $162 to $324/night

  61. CONDOMINIUM
    Keawakapu Views #206

    Keawakapu Views #206

    Kihei, HI

    FREE CANCELLATION

    $157 to $261/night

  62. CONDOMINIUM
    Wailea Ekolu #201

    Wailea Ekolu #201

    Wailea, HI

    Pool
    FREE CANCELLATION

    $290 to $487/night

  63. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  64. CONDOMINIUM
    Kihei Akahi #D-112

    Kihei Akahi #D-112

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  65. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  66. CONDOMINIUM
    Wailea Ekolu #205

    Wailea Ekolu #205

    Wailea, HI

    Pool
    FREE CANCELLATION

    $307 to $522/night

  67. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

  68. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  69. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  70. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $409/night

  71. HOUSE
    Hanalei Bay Villa 26

    Hanalei Bay Villa 26

    Princeville, HI

    FREE CANCELLATION

    $268 to $336/night

  72. CONDOMINIUM
    Pacific Shores #A-101

    Pacific Shores #A-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $158 to $244/night

  73. CONDOMINIUM
    Grand Champions #65

    Grand Champions #65

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $464/night

  74. CONDOMINIUM
    Menehune Shores #401

    Menehune Shores #401

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  75. CONDOMINIUM
    Kihei Bay Surf #253

    Kihei Bay Surf #253

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  76. TOWNHOUSE
    Palm Villas F4 at Mauna Lani Resort

    Palm Villas F4 at Mauna Lani Resort

    Kamuela, HI

    Pool
    FREE CANCELLATION

    $364 to $608/night

  77. 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

  78. CONDOMINIUM
    Hale Kamaole #318

    Hale Kamaole #318

    Kihei, HI

    Pool
    FREE CANCELLATION

    $249 to $348/night

  79. CONDOMINIUM
    Pacific Shores #A-303

    Pacific Shores #A-303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $300/night

  80. CONDOMINIUM
    Kihei Garden Estates #E-102

    Kihei Garden Estates #E-102

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $244/night

  81. CONDOMINIUM
    Palms at Wailea #1604

    Palms at Wailea #1604

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $383/night

  82. CONDOMINIUM
    Shores of Maui #211

    Shores of Maui #211

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $335/night

  83. CONDOMINIUM
    Hale Kamaole #101

    Hale Kamaole #101

    Kihei, HI

    Pool
    FREE CANCELLATION

    $231 to $331/night

  84. CONDOMINIUM
    Maui Vista #3-404

    Maui Vista #3-404

    Kihei, HI

    Pool
    FREE CANCELLATION

    $219 to $348/night

  85. CONDOMINIUM
    Shores of Maui #124

    Shores of Maui #124

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $209/night

  86. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  87. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  88. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  89. CONDOMINIUM
    Kihei Bay Surf #257

    Kihei Bay Surf #257

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  90. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $114 to $399/night

  91. 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

  92. CONDOMINIUM
    Kihei Bay Surf #226

    Kihei Bay Surf #226

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  93. HOUSE
    Ohana Retreat

    Ohana Retreat

    Princeville, HI

    $247 to $340/night

  94. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $572/night

  95. CONDOMINIUM
    Noelani # 115

    Noelani # 115

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $437/night

  96. 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

  97. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  98. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  99. CONDOMINIUM
    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $220 to $238/night

  100. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night