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. $2,203 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
  7. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  8. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  9. $1,761 to $2,076/night

    WAILEA ELUA, #1305^

    WAILEA ELUA, #1305^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  10. $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
  11. $1,663 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  12. $1,553 to $3,338/night

    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  13. $1,261 to $4,648/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  14. $1,248 to $4,276/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
  15. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  16. $1,165 to $3,966/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
  17. $1,162 to $1,252/night

    Hale Lani

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  18. $1,109 to $1,111/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
  19. $1,102 to $3,791/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
  20. $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
  21. $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
  22. $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
  23. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  24. $975 to $1,395/night

    Kona Bubbles

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  25. $897 to $1,459/night

    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  26. $897 to $1,572/night

    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  27. $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
  28. $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
  29. $858 to $1,955/night

    Honua Kai-Konea #925

    Honua Kai-Konea #925

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $855 to $1,319/night

    MAKENA SURF RESORT, #B-204

    MAKENA SURF RESORT, #B-204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  31. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  32. $855 to $1,319/night

    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  33. $844 to $2,781/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
  34. $799 to $2,616/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  35. $785 to $1,459/night

    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  36. $781 to $1,219/night

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  37. $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
  38. $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
  39. $775 to $1,094/night

    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  40. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  41. $775 to $1,094/night

    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  42. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  43. $762 to $1,094/night

    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  44. $757 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $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
  46. $724 to $1,065/night

    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  47. $724 to $1,065/night

    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  48. $724 to $1,065/night

    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  49. $706 to $1,038/night

    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  50. $706 to $1,038/night

    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  51. $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
  52. $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
  53. $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
  54. $650 to $1,038/night

    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  55. $634 to $896/night

    WAILEA ELUA, #1309

    WAILEA ELUA, #1309

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  56. $631 to $1,403/night

    Koa Kai Hale

    Koa Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  57. $625 to $1,651/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
  58. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $613 to $764/night

    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  61. $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
  62. $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
  63. $594 to $1,063/night

    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  64. $584/night

    Koana Breeze

    Koana Breeze

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  65. $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
  66. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  67. $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
  68. $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
  69. $571 to $1,789/night

    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  70. $563 to $781/night

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  71. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  72. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  73. $556 to $1,063/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  74. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  75. $538 to $1,065/night

    WAILEA ELUA, #0202*

    WAILEA ELUA, #0202*

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  76. $531 to $969/night

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  77. $531 to $969/night

    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua Bay Villa 32B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  78. $525 to $869/night

    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
  79. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $525 to $906/night

    Kapalua Ridge Villa 1523 Gold Ocean View

    Kapalua Ridge Villa 1523 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  81. $525 to $869/night

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  82. $513 to $977/night

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  83. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $513 to $1,789/night

    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  85. $512 to $1,371/night

    Pili Mai 8D

    Pili Mai 8D

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  86. $508 to $1,789/night

    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  87. $508 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
  88. $506 to $2,169/night

    Waterfall House

    Waterfall House

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  89. $506 to $563/night

    Sands Of Kahana 234

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  90. $506 to $563/night

    Sands Of Kahana 315

    Sands Of Kahana 315

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  91. $506 to $563/night

    Sands Of Kahana 215

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  92. $506 to $563/night

    Sands Of Kahana 272

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  93. $505 to $711/night

    Papakea A404

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  94. $504 to $1,094/night

    MAKENA SURF RESORT, #F-209

    MAKENA SURF RESORT, #F-209

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  95. $504 to $896/night

    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  96. $504 to $896/night

    WAILEA ELUA, #1601

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  97. $501 to $1,093/night

    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  98. $501 to $1,325/night

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  99. $501 to $619/night

    Sands of Kahana 366

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  100. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub