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. $2,743 to $6,408/night

    Blue Lagoon*

    Blue Lagoon*

    7 BedroomsBathroomsSleeps 14
    2 nights minstay
  7. $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
  8. $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
  9. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

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

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  11. $1,870 to $2,494/night

    Wilikoki House

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  12. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  13. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  14. $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
  15. $1,678 to $5,448/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  16. $1,660 to $2,076/night

    WAILEA ELUA, #1305^

    WAILEA ELUA, #1305^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  17. $1,603 to $2,345/night

    Rainbow Hale Estate

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  18. $1,553 to $3,338/night

    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  19. $1,514 to $2,750/night

    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
  20. $1,434 to $3,937/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  21. $1,434 to $3,267/night

    Blue Oasis*

    Blue Oasis*

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  22. $1,392 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  23. $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
  24. $1,315 to $2,935/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  25. $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
  26. $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
  27. $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
  28. $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
  29. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  30. $1,162 to $1,193/night

    Hale Lani

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  31. $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
  32. $1,148 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
  33. $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
  34. $1,137 to $2,029/night

    Ali'i Villa

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  35. $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
  36. $1,103/night

    Diamond Head Beach Hotel Rooftop 1402

    Diamond Head Beach Hotel Rooftop 1402

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  37. $1,094 to $1,413/night

    Moloa'a Bay Villa

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
  38. $1,066 to $1,459/night

    MAKENA SURF RESORT, #G-304

    MAKENA SURF RESORT, #G-304

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  39. $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
  40. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $1,018 to $1,880/night

    Mauna Kea Villas #13

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  43. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  44. $1,008 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  45. $1,000 to $2,933/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $958 to $1,129/night

    Punahele Point

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
  47. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  48. $921 to $1,395/night

    Kona Bubbles

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  49. $899 to $1,434/night

    Hale Kauka

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  50. $899 to $2,409/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  51. $897 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  52. $897 to $1,459/night

    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  53. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  54. $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
  55. $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
  56. $861 to $1,169/night

    Whaler at Kaanapali Beach 723

    Whaler at Kaanapali Beach 723

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $861 to $1,169/night

    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $858 to $2,575/night

    Honua Kai-Konea #925

    Honua Kai-Konea #925

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $855 to $1,319/night

    MAKENA SURF RESORT, #B-204

    MAKENA SURF RESORT, #B-204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  60. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  61. $855 to $1,319/night

    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  62. $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
  63. $790 to $1,051/night

    Hale Ola Kai

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  64. $784 to $2,125/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  65. $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
  66. $781 to $1,219/night

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  67. $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
  68. $781 to $1,219/night

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  69. $781 to $1,219/night

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  70. $780 to $1,398/night

    Hale Poola

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  71. $780 to $1,369/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  72. $775 to $1,094/night

    MAKENA SURF RESORT, #F-209

    MAKENA SURF RESORT, #F-209

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  73. $775 to $1,094/night

    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  74. $775 to $1,094/night

    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  75. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  76. $775 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  77. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  78. $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
  79. $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
  80. $750 to $1,624/night

    Hokulani Villa

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  81. $748 to $1,060/night

    Malapua

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  82. $744 to $2,194/night

    Blue Hawaii

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  83. $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
  84. $724 to $1,065/night

    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  85. $724 to $1,065/night

    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  86. $719 to $1,413/night

    Nai'a Hale

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  87. $717 to $904/night

    Hale Koaniani

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  88. $708 to $1,878/night

    Pineapple Hale

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $706 to $1,038/night

    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  90. $706 to $1,038/night

    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  91. $706 to $1,038/night

    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  92. $690 to $1,491/night

    Hale Anu Keanu

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  93. $690 to $1,867/night

    Pohaku Villa

    Pohaku Villa

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
  94. $690 to $1,624/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  95. $688 to $1,575/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  96. $687 to $1,828/night

    Hoku'Ea Hale

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  97. $686 to $936/night

    Hale A Kai

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  98. $686 to $873/night

    Lokelani Hale

    Lokelani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  99. $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
  100. $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