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
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  2. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  3. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Pool Hot Tub

    $608 to $2,348/night

  4. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $829/night

  5. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  6. CONDOMINIUM
    Kahana Sunset B7

    Kahana Sunset B7

    Lahaina, HI

    Pool

    $309 to $366/night

  7. CONDOMINIUM
    Kahana Sunset D10

    Kahana Sunset D10

    Lahaina, HI

    Pool

    $253 to $309/night

  8. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  9. CONDOMINIUM
    Kahana Sunset D8

    Kahana Sunset D8

    Lahaina, HI

    Pool

    $276 to $332/night

  10. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  11. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  12. CONDOMINIUM
    Kahana Sunset C7

    Kahana Sunset C7

    Lahaina, HI

    Pool

    $276 to $332/night

  13. 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

    $203 to $632/night

  14. CONDOMINIUM
    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $403 to $1,539/night

  15. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $420 to $479/night

  16. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759/night

  17. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  18. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  19. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  20. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $331/night

  21. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $536 to $1,308/night

  22. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $183 to $407/night

  23. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $557/night

  24. CONDOMINIUM
    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Kaanapali, HI

    Pool Hot Tub

    $1,118/night

  25. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $264/night

  26. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,668/night

  27. 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

    $171 to $445/night

  28. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370/night

  29. CONDOMINIUM
    Kahana Sunset B3B

    Kahana Sunset B3B

    Lahaina, HI

    Pool

    $214/night

  30. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $270/night

  31. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $484/night

  32. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $253/night

  33. CONDOMINIUM
    Kahana Sunset B3

    Kahana Sunset B3

    Lahaina, HI

    Pool

    $366/night

  34. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $332/night

  35. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  36. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  37. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Kaanapali, HI

    Pool Hot Tub

    $522 to $1,992/night

  38. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $1,245/night

  39. CONDOMINIUM
    Kahana Sunset A4

    Kahana Sunset A4

    Lahaina, HI

    Pool

    $428 to $484/night

  40. CONDOMINIUM
    Kahana Sunset D7

    Kahana Sunset D7

    Lahaina, HI

    Pool

    $276 to $332/night

  41. CONDOMINIUM
    Bay Villa 38G3

    Bay Villa 38G3

    Lahaina, HI

    Pool

    $248 to $304/night

  42. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  43. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  44. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $181 to $312/night

  45. CONDOMINIUM
    Kahana Sunset C4

    Kahana Sunset C4

    Lahaina, HI

    Pool

    $219 to $276/night

  46. COTTAGE
    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $170 to $217/night

  47. COTTAGE
    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Honolulu, HI

    FREE CANCELLATION

    $121 to $182/night

  48. HOUSE
    Lokelani Hale

    Lokelani Hale

    Hanalei, HI

    FREE CANCELLATION

    $686 to $873/night

  49. CONDOMINIUM
    Hanalei Bay Villas #16

    Hanalei Bay Villas #16

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  50. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  51. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $804/night

  52. HOUSE
    Ohana House

    Ohana House

    Hanalei, HI

    FREE CANCELLATION

    $499 to $562/night

  53. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $360 to $479/night

  54. CONDOMINIUM
    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $540/night

  55. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $454/night

  56. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $466/night

  57. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $2,802/night

  58. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231/night

  59. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,323 to $1,324/night

  60. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club#7-102 "Honu Hale"

    Keauhou Kona Surf & Racquet Club#7-102 "Honu Ha...

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $292/night

  61. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $619/night

  62. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $445/night

  63. CONDOMINIUM
    Kahana Reef 107

    Kahana Reef 107

    Lahaina, HI

    FREE CANCELLATION

    $495/night

  64. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $401/night

  65. CONDOMINIUM
    Honua kai- Konea 301 Frontline with BBQ!

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $2,056/night

  66. CONDOMINIUM
    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $1,646/night

  67. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $239 to $353/night

  68. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $183 to $407/night

  69. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  70. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  71. CONDOMINIUM
    PentHouse 701

    PentHouse 701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $370/night

  72. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $424/night

  73. CONDOMINIUM
    Kahana Sunset D6

    Kahana Sunset D6

    Lahaina, HI

    Pool

    $332/night

  74. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $563/night

  75. CONDOMINIUM
    Kahana Sunset B1B

    Kahana Sunset B1B

    Lahaina, HI

    Pool

    $270/night

  76. CONDOMINIUM
    Kahana Sunset D9

    Kahana Sunset D9

    Lahaina, HI

    Pool

    $332/night

  77. CONDOMINIUM
    Kahana Sunset C1C

    Kahana Sunset C1C

    Lahaina, HI

    Pool

    $270/night

  78. CONDOMINIUM
    Ridge Villa 1222

    Ridge Villa 1222

    LAHAINA, HI

    Pool Hot Tub

    $248/night

  79. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $501/night

  80. CONDOMINIUM
    Bay Villa 38G2

    Bay Villa 38G2

    Lahaina, HI

    Pool

    $304/night

  81. APARTMENT
    Condo with Ocean View! Right on a Golf Course & Minutes from the Beach!

    Condo with Ocean View! Right on a Golf Course & Minu...

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $152 to $213/night

  82. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  83. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night

  84. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  85. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  86. CONDOMINIUM
    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b/1b

    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b...

    Kaanapali, HI

    Pool Hot Tub

    $254 to $908/night

  87. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  88. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  89. CONDOMINIUM
    Kahana Sunset D2D

    Kahana Sunset D2D

    Lahaina, HI

    Pool

    $186 to $270/night

  90. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $499 to $686/night

  91. CONDOMINIUM
    Kahana Sunset E8

    Kahana Sunset E8

    Lahaina, HI

    Pool

    $276 to $332/night

  92. CONDOMINIUM
    Grand Champions 124

    Grand Champions 124

    Kihei, HI

    Pool
    FREE CANCELLATION

    $313 to $849/night

  93. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $241 to $389/night

  94. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $138 to $316/night

  95. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $454/night

  96. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $211 to $330/night

  97. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $3,125/night

  98. CONDOMINIUM
    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3.5b

    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3....

    Kaanapali, HI

    Pool Hot Tub

    $3,251/night

  99. CONDOMINIUM
    Kona Pacific B511

    Kona Pacific B511

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $158 to $215/night

  100. CONDOMINIUM
    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $1,957/night

  101. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $557/night

  102. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  103. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $413/night

  104. CONDOMINIUM
    Kahana Sunset B8

    Kahana Sunset B8

    Lahaina, HI

    Pool

    $366/night

  105. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $388/night

  106. CONDOMINIUM
    Kahana Sunset B1

    Kahana Sunset B1

    Lahaina, HI

    Pool

    $309/night

  107. CONDOMINIUM
    Kahana Sunset B5B

    Kahana Sunset B5B

    Lahaina, HI

    Pool

    $270/night