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. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  2. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  3. $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
  4. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  5. $3,248 to $5,568/night

    Wailea Inn Maui

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 35
    2 nights minstay
  6. $2,505 to $4,766/night

    Mauna Kea Resort Townhouse- Kaunaoa 7B (4BR/4.5BA)

    Mauna Kea Resort Townhouse- Kaunaoa 7B (4BR/4.5BA)

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  7. $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
  8. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $1,900 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  10. $1,870 to $2,494/night

    Wilikoki House

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  11. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  12. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  13. $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
  14. $1,678 to $5,448/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  15. $1,553 to $3,338/night

    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  16. $1,434 to $3,937/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  17. $1,392 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  18. $1,373 to $3,458/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
  19. $1,315 to $2,935/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  20. $1,314 to $4,289/night

    Lau'lea at the Mauna Lani*

    Lau'lea at the Mauna Lani*

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  21. $1,265 to $3,948/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  22. $1,231 to $3,633/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
  23. $1,198 to $3,374/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
  24. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  25. $1,162 to $1,193/night

    Hale Lani

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. $1,160 to $3,743/night

    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  27. $1,158 to $3,230/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
  28. $1,137 to $2,029/night

    Ali'i Villa

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  29. $1,137 to $2,660/night

    Ke Kailani Hale A2

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  30. $1,109/night

    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $1,103/night

    Diamond Head Beach Hotel Rooftop 1402

    Diamond Head Beach Hotel Rooftop 1402

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  32. $1,094 to $1,413/night

    Moloa'a Bay Villa

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
  33. $1,063 to $3,447/night

    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  34. $1,018 to $1,880/night

    Mauna Kea Villas #13

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  35. $1,008 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  36. $1,000 to $2,933/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $958 to $1,129/night

    Punahele Point

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
  38. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  39. $916 to $1,395/night

    Kona Bubbles

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  40. $899 to $1,434/night

    Hale Kauka

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  41. $899 to $2,409/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  42. $881 to $2,413/night

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  43. $866 to $2,371/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
  44. $813 to $1,219/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  45. $790 to $1,051/night

    Hale Ola Kai

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  46. $784 to $2,125/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  47. $781 to $1,219/night

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  48. $781 to $1,219/night

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  49. $781 to $1,219/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  50. $780 to $1,398/night

    Hale Poola

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  51. $780 to $1,369/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  52. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  53. $755 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $750 to $1,156/night

    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  55. $750 to $1,624/night

    Hokulani Villa

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  56. $748 to $1,060/night

    Malapua

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  57. $744 to $2,194/night

    Blue Hawaii

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  58. $740 to $2,021/night

    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  59. $719 to $1,413/night

    Nai'a Hale

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  60. $717 to $904/night

    Hale Koaniani

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  61. $708 to $1,878/night

    Pineapple Hale

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. $690 to $1,491/night

    Hale Anu Keanu

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  63. $690 to $1,867/night

    Pohaku Villa

    Pohaku Villa

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
  64. $690 to $1,624/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  65. $688 to $1,464/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  66. $687 to $1,828/night

    Hoku'Ea Hale

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  67. $686 to $936/night

    Hale A Kai

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  68. $686 to $873/night

    Lokelani Hale

    Lokelani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  69. $668 to $846/night

    Ali'i Point #5 Oceanfront

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. $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
  71. $661 to $1,899/night

    Hale Kai O'Kona #7

    Hale Kai O'Kona #7

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
  72. $661 to $1,910/night

    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  73. $656 to $906/night

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  74. $656 to $875/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  75. $643/night

    Alii Villas C-125 (Duplicate NID 194494)

    Alii Villas C-125 (Duplicate NID 194494)

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  76. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  77. $631 to $1,341/night

    Koa Kai Hale

    Koa Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  78. $631 to $1,536/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  79. $625 to $1,650/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $623 to $748/night

    Hale Kalani

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  81. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $616 to $1,601/night

    Honu O Kai (Turtle of the Sea)

    Honu O Kai (Turtle of the Sea)

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  83. $608 to $790/night

    Hale Huna Kai- Oceanfront

    Hale Huna Kai- Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  84. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  85. $608 to $846/night

    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $604 to $1,080/night

    Manoa Valley 2BR w/ Hot Tub & Lanai w/ Ocean View

    Manoa Valley 2BR w/ Hot Tub & Lanai w/ Ocean View

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Hot Tub Pets OK
    FREE CANCELLATION
  87. $601 to $1,325/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  88. $599 to $1,389/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  89. $599 to $1,459/night

    Piko Nani

    Piko Nani

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  90. $595 to $1,275/night

    Hale Kanani (Kaua'i) TVNC 1342

    Hale Kanani (Kaua'i) TVNC 1342

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
  91. $594 to $969/night

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    2 Bedrooms2.25 BathroomsSleeps 6
    4 nights minstay
    Pool
  92. $594 to $1,063/night

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  93. $589 to $1,389/night

    Ho'o Maluhia

    Ho'o Maluhia

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  94. $584/night

    Koana Breeze

    Koana Breeze

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  95. $582 to $1,325/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  96. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  97. $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
  98. $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
  99. $577 to $722/night

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  100. $576 to $883/night

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION