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
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    Pool Hot Tub

    $481 to $1,285/night

  2. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  3. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  4. ESTATE
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    Pool Hot Tub

    $3,695 to $6,075/night

  5. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  6. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  7. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    Pool Hot Tub

    $235 to $301/night

  8. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  9. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  10. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  11. CONDOMINIUM
    Plantation 1111

    Plantation 1111

    Princeville, HI

    Pool Hot Tub

    $241 to $271/night

  12. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  13. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  14. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  15. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  16. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $990/night

  17. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  18. VILLA
    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $923 to $3,027/night

  19. 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

    $539 to $1,965/night

  20. 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 $1,655/night

  21. CONDOMINIUM
    Vista Waikoloa C305

    Vista Waikoloa C305

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $538/night

  22. 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

    $133 to $453/night

  23. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  24. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,917 to $5,992/night

  25. CONDOMINIUM
    Maui Kai 201

    Maui Kai 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $323 to $551/night

  26. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  27. 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

    $887 to $3,264/night

  28. 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

    $257 to $912/night

  29. CONDOMINIUM
    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    Kapaa, HI

    Pool Hot Tub

    $311 to $386/night

  30. CONDOMINIUM
    Ridge Villa 1222

    Ridge Villa 1222

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  31. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $464/night

  32. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  33. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  34. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  35. CONDOMINIUM
    Sands Of Kahana 134

    Sands Of Kahana 134

    Lahaina, HI

    Pool Hot Tub

    $298 to $354/night

  36. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  37. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  38. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  39. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $353/night

  40. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  41. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    Princeville, HI

    Pool Hot Tub

    $422 to $542/night

  42. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Pool Hot Tub

    $253 to $271/night

  43. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  44. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $499 to $853/night

  45. TOWNHOUSE
    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $631/night

  46. HOUSE
    Kolea 14F at the Waikoloa Beach Resort

    Kolea 14F at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $1,061/night

  47. CONDOMINIUM
    Beach Villas M3

    Beach Villas M3

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $140 to $481/night

  48. CONDOMINIUM
    Palm Villa I3 at the Mauna Lani Resort

    Palm Villa I3 at the Mauna Lani Resort

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $225 to $793/night

  49. CONDOMINIUM
    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $438 to $1,358/night

  50. CONDOMINIUM
    Hali'i Kai at Waikoloa Beach Resort 9F

    Hali'i Kai at Waikoloa Beach Resort 9F

    Waikoloa, HI

    Pool Hot Tub

    $450 to $1,578/night

  51. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  52. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  53. CONDOMINIUM
    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  54. 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

    $220 to $424/night

  55. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

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

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $566 to $2,227/night

  57. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $825 to $2,813/night

  58. 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

    $531 to $2,001/night

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

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

    Kaanapali, HI

    Pool Hot Tub

    $550 to $1,554/night

  60. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana

    Mauna Kea Bluffs #5: La Ikena O Komohana

    Kamuela, HI

    Pool Hot Tub

    $10,240 to $12,620/night

  61. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $970 to $2,858/night

  62. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  63. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  64. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Pool Hot Tub

    $1,060 to $3,293/night

  65. CONDOMINIUM
    Close to the Beach, Shopping and Adventures! 3 Bed Condo

    Close to the Beach, Shopping and Adventures! 3 Bed Condo...

    Kohala Coast, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $426/night

  66. 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

  67. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  68. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  69. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Pool Hot Tub

    $211 to $235/night

  70. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  71. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  72. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  73. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  74. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  75. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $760/night

  76. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  77. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  78. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  79. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $370/night

  80. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  81. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $624/night

  82. 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

  83. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  84. HOUSE
    Fairway Villas I34 at the Waikoloa Beach Resort

    Fairway Villas I34 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $538/night

  85. TOWNHOUSE
    Mauna Lani Fairways #803

    Mauna Lani Fairways #803

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $679/night

  86. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $309 to $1,061/night

  87. HOUSE
    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $538/night

  88. CONDOMINIUM
    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $125 to $466/night

  89. TOWNHOUSE
    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $651/night

  90. HOUSE
    WAILEA ELUA, #2003

    WAILEA ELUA, #2003

    Wailea, Maui, HI

    Pool Hot Tub

    $448 to $823/night

  91. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $369/night

  92. 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

  93. 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

    $316 to $1,123/night

  94. 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

    $322 to $1,154/night

  95. CONDOMINIUM
    The Montage Kapalua Bay- Heliconia 2302- Ocean View Paradise!

    The Montage Kapalua Bay- Heliconia 2302- Ocean View Para...

    Kapalua, HI

    Pool Hot Tub

    $1,297 to $3,687/night

  96. 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

    $644 to $2,357/night

  97. 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

    $426 to $1,544/night