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. $4,194 to $7,190/night

    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  2. $3,248 to $5,568/night

    Wailea Inn Maui

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 35
    2 nights minstay
  3. $2,203 to $4,290/night

    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  4. $1,734 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  5. $1,373 to $3,451/night

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18)

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    4 Bedrooms4.5 BathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
  6. $1,266 to $3,945/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  7. $1,231 to $3,630/night

    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  8. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  9. $1,160 to $3,738/night

    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  10. $1,148 to $3,370/night

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

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

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  11. $1,084 to $3,226/night

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

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  12. $1,063 to $3,444/night

    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  13. $899 to $2,678/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  14. $827 to $2,367/night

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  15. $783 to $2,229/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  16. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  17. $661 to $1,910/night

    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  18. $625 to $1,585/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  19. $579 to $984/night

    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Steps To Beach

    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Ste...

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  20. $579 to $984/night

    Luxury 3 bedroom Hideaway near the beach

    Luxury 3 bedroom Hideaway near the beach

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  21. $542 to $1,328/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  22. $542 to $1,234/night

    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  23. $512 to $1,369/night

    Pili Mai 8D

    Pili Mai 8D

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  24. $500 to $1,147/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  25. $485 to $652/night

    Hale Ulu'wehi

    Hale Ulu'wehi

    4 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  26. $482 to $1,220/night

    Pili Mai 7M

    Pili Mai 7M

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  27. $481 to $899/night

    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  28. $476 to $1,367/night

    Hallor House TVNC #5147

    Hallor House TVNC #5147

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  29. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  30. $423 to $730/night

    Pili Mai 11I

    Pili Mai 11I

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  31. $416 to $786/night

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To Beach

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  32. $409 to $1,038/night

    Pili Mai 6K

    Pili Mai 6K

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  33. $399 to $720/night

    Mauna Lani Golf Villas C1

    Mauna Lani Golf Villas C1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  34. $392 to $523/night

    Plantation Cottage

    Plantation Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  35. $375 to $720/night

    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  36. $375 to $576/night

    Ilikai 1418

    Ilikai 1418

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $371 to $495/night

    Diamond Head Beach Hotel 501

    Diamond Head Beach Hotel 501

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $363 to $869/night

    Pili Mai 3G

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  39. $347 to $466/night

    Hale Kohola

    Hale Kohola

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  40. $338 to $576/night

    Ilikai 526

    Ilikai 526

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $330 to $689/night

    Big Island Paradise

    Big Island Paradise

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  42. $326 to $350/night

    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  43. $322 to $641/night

    Leilani

    Leilani

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  44. $321 to $444/night

    Diamond Head Beach Hotel 601

    Diamond Head Beach Hotel 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  45. $314 to $764/night

    Poipu Crater

    Poipu Crater

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  46. $310 to $605/night

    Melemele Pua

    Melemele Pua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  47. $294 to $598/night

    Hale Mali'e

    Hale Mali'e

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  48. $286 to $478/night

    Hale Ohana Aloha

    Hale Ohana Aloha

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  49. $280 to $596/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  50. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  51. $249 to $312/night

    Riko Hale

    Riko Hale

    2 Bedrooms BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  52. $249 to $312/night

    Malolo Cottage

    Malolo Cottage

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  53. $248 to $309/night

    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. $238 to $478/night

    Hale 'Olu'Olu

    Hale 'Olu'Olu

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  55. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  56. $219 to $280/night

    Emmalani Court #525

    Emmalani Court #525

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  57. $219 to $280/night

    OTA House

    OTA House

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  58. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  59. $213 to $309/night

    Diamond Head Beach Hotel 602

    Diamond Head Beach Hotel 602

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  60. $193 to $255/night

    Holoholo ku Waimea

    Holoholo ku Waimea

    3 BedroomsBathroomsSleeps 6
    14 nights minstay
    FREE CANCELLATION
  61. $179 to $325/night

    Ilikai 2040

    Ilikai 2040

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. $178 to $319/night

    Hale Ono Loa #316

    Hale Ono Loa #316

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  63. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $168 to $325/night

    Ilikai 2114

    Ilikai 2114

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $157 to $312/night

    Ilikai 1904

    Ilikai 1904

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $156 to $250/night

    Ilikai 1507

    Ilikai 1507

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $156 to $312/night

    Ilikai 1636

    Ilikai 1636

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $152 to $300/night

    Ilikai 1737

    Ilikai 1737

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $146 to $300/night

    Ilikai 1038

    Ilikai 1038

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $146 to $287/night

    Ilikai 1437

    Ilikai 1437

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $146 to $312/night

    Ilikai Marina 1792

    Ilikai Marina 1792

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  72. $146 to $300/night

    Ilikai 604

    Ilikai 604

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  73. $146 to $306/night

    Ilikai 1927

    Ilikai 1927

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $146 to $312/night

    Ilikai 1827

    Ilikai 1827

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $146 to $312/night

    Ilikai 1130

    Ilikai 1130

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $146 to $312/night

    Ilikai 1938

    Ilikai 1938

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $141 to $287/night

    Ilikai Marina 1192

    Ilikai Marina 1192

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  78. $141 to $250/night

    Ilikai Marina 482

    Ilikai Marina 482

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  79. $141 to $250/night

    Ilikai Marina 484

    Ilikai Marina 484

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  80. $132 to $245/night

    Ilikai 427

    Ilikai 427

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  81. $124 to $174/night

    Waikiki Grand 411

    Waikiki Grand 411

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. $102 to $162/night

    AV 302

    AV 302

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  83. $100 to $359/night

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION