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. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $553 to $1,159/night

  2. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

  3. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  4. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  5. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  6. CONDOMINIUM
    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  7. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $337/night

  8. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  9. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  10. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  11. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    FREE CANCELLATION

    $360 to $557/night

  12. CONDOMINIUM
    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  13. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  14. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $343 to $540/night

  15. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  16. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  17. HOUSE
    Hale Koaniani

    Hale Koaniani

    Wainiha, HI

    FREE CANCELLATION

    $717 to $904/night

  18. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $686/night

  19. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  20. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $494/night

  21. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $494/night

  22. CONDOMINIUM
    Hale Ono Loa 109

    Hale Ono Loa 109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $1,170/night

  23. CONDOMINIUM
    Hale Ono Loa 214

    Hale Ono Loa 214

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $513/night

  24. CONDOMINIUM
    Hale Ono Loa 402

    Hale Ono Loa 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $351/night

  25. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $304 to $581/night

  26. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $264/night

  27. HOUSE
    Hoku'Ea Hale

    Hoku'Ea Hale

    Kailua Kona, HI

    Hot Tub

    $566 to $788/night

  28. CONDOMINIUM
    Hololani A303

    Hololani A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $488/night

  29. CONDOMINIUM
    Hololani A701

    Hololani A701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $474/night

  30. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $413/night

  31. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $508 to $988/night

  32. CONDOMINIUM
    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View! 1b/1b

    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View!...

    Kaanapali, HI

    Pool Hot Tub

    $908/night

  33. CONDOMINIUM
    Honua Kai- Konea 606- Partial Ocean and Mountain Views! 2b/1b

    Honua Kai- Konea 606- Partial Ocean and Mountain Views! ...

    Kaanapali, HI

    Pool Hot Tub

    $320 to $1,197/night

  34. CONDOMINIUM
    Hoyochi Nikko 108

    Hoyochi Nikko 108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $166 to $660/night

  35. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  36. COTTAGE
    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    Kamuela, HI

    FREE CANCELLATION

    $436 to $916/night

  37. CONDOMINIUM
    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Honolulu, HI

    FREE CANCELLATION

    $219 to $731/night

  38. CONDOMINIUM
    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Honolulu, HI

    FREE CANCELLATION

    $219 to $731/night

  39. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $346 to $965/night

  40. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $336 to $1,016/night

  41. CONDOMINIUM
    Kaanapali Shores 613

    Kaanapali Shores 613

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $1,016/night

  42. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $1,118/night

  43. CONDOMINIUM
    Kahana Reef 106

    Kahana Reef 106

    Lahaina, HI

    FREE CANCELLATION

    $124 to $461/night

  44. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $154 to $381/night

  45. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $461/night

  46. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $169 to $548/night

  47. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $150 to $275/night

  48. CONDOMINIUM
    Kaleialoha 402

    Kaleialoha 402

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $115 to $468/night

  49. CONDOMINIUM
    Kaleialoha 406

    Kaleialoha 406

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $194 to $331/night

  50. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  51. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  52. CONDOMINIUM
    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $750/night

  53. CONDOMINIUM
    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $823/night

  54. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $471/night

  55. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $464/night

  56. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $27,561/night

  57. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $334/night

  58. 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

  59. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $311 to $350/night

  60. CONDOMINIUM
    Kona Alii 403

    Kona Alii 403

    Kailua Kona, HI

    Pool

    $374/night

  61. CONDOMINIUM
    Kona Makai 6301

    Kona Makai 6301

    Kailua Kona, HI

    Pool

    $409/night

  62. CONDOMINIUM
    Kona Nalu 304

    Kona Nalu 304

    Kailua Kona, HI

    Pool

    $263 to $397/night

  63. CONDOMINIUM
    Kulakane 211

    Kulakane 211

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $149 to $461/night

  64. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  65. CONDOMINIUM
    Kulakane 306

    Kulakane 306

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $281 to $311/night

  66. CONDOMINIUM
    Kulakane 307

    Kulakane 307

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $531/night

  67. CONDOMINIUM
    Kuleana 208 1 Bdrm

    Kuleana 208 1 Bdrm

    Lahaina, HI

    FREE CANCELLATION

    $225 to $423/night

  68. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $596/night

  69. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $251 to $346/night

  70. CONDOMINIUM
    Lauloa 105

    Lauloa 105

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $175 to $438/night

  71. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $152 to $239/night

  72. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $804/night

  73. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $241 to $749/night

  74. CONDOMINIUM
    Mahana 1008

    Mahana 1008

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $266 to $1,105/night

  75. CONDOMINIUM
    Mahana 1113

    Mahana 1113

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $1,158/night

  76. CONDOMINIUM
    Mahana 307

    Mahana 307

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $869/night

  77. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $1,245/night

  78. CONDOMINIUM
    Mahana 602

    Mahana 602

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $178 to $763/night

  79. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,313/night

  80. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $724/night

  81. CONDOMINIUM
    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  82. CONDOMINIUM
    Maui Kai 108

    Maui Kai 108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $485/night

  83. CONDOMINIUM
    Maui Kai 206

    Maui Kai 206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $438/night

  84. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $606/night

  85. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $499/night

  86. CONDOMINIUM
    Maui Kai 605

    Maui Kai 605

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $306/night

  87. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $298/night

  88. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $729 to $759/night

  89. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469/night

  90. CONDOMINIUM
    Napili Point B44

    Napili Point B44

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $711/night

  91. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $250 to $625/night

  92. CONDOMINIUM
    Napili Point C-12 2bdrm/2bath

    Napili Point C-12 2bdrm/2bath

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $410 to $641/night

  93. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $581/night

  94. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $311/night

  95. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $437/night

  96. CONDOMINIUM
    Nohonani #202

    Nohonani #202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $403/night

  97. HOUSE
    Oceanfront 3BR, Breathtaking Views

    Oceanfront 3BR, Breathtaking Views

    Captain Cook, HI

    FREE CANCELLATION

    $234 to $545/night

  98. CONDOMINIUM
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $199 to $602/night

  99. HOUSE
    Pacific Edge Kona

    Pacific Edge Kona

    Kailua Kona, HI

    $309 to $438/night

  100. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $799/night

  101. CONDOMINIUM
    Papakea B405

    Papakea B405

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,450/night

  102. CONDOMINIUM
    Papakea G301

    Papakea G301

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $286/night

  103. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $3,125/night

  104. CONDOMINIUM
    Polynesian Shores 111

    Polynesian Shores 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $113 to $455/night

  105. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $153 to $668/night

  106. CONDOMINIUM
    Sands of Kahana 354

    Sands of Kahana 354

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,185/night

  107. CONDOMINIUM
    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $444/night

  108. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $312/night

  109. CONDOMINIUM
    Valley Isle 902

    Valley Isle 902

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $144 to $461/night

  110. CONDOMINIUM
    Wailea Ekahi 36C

    Wailea Ekahi 36C

    Wailea, HI

    Pool
    FREE CANCELLATION

    $419/night

  111. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Pool
    FREE CANCELLATION

    $167 to $490/night

  112. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $720/night