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. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  2. 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

  3. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/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. VILLA
    Wailea Inn Maui

    Wailea Inn Maui

    Kihei, HI

    $3,248 to $5,568/night

  6. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

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

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

    Kihei, HI

    $1,995 to $26,094/night

  8. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  9. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  10. CONDOMINIUM
    WAILEA ELUA, #1305^

    WAILEA ELUA, #1305^

    Wailea, Maui, HI

    Pool Hot Tub

    $1,761 to $2,076/night

  11. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  12. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  13. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,256 to $1,395/night

  14. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  15. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  16. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,157 to $1,536/night

  17. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,077 to $3,318/night

  18. CONDOMINIUM
    MAKENA SURF RESORT, #G-304

    MAKENA SURF RESORT, #G-304

    Makena, Maui, HI

    Pool Hot Tub

    $1,066 to $1,459/night

  19. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,605/night

  20. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  21. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  22. 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

    $977 to $3,081/night

  23. 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

    $934 to $2,945/night

  24. CONDOMINIUM
    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    Wailea, Maui, HI

    Pool Hot Tub

    $931 to $1,459/night

  25. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,564/night

  26. CONDOMINIUM
    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    Makena, Maui, HI

    Pool Hot Tub

    $855 to $1,319/night

  27. CONDOMINIUM
    Whaler at Kaanapali Beach 723

    Whaler at Kaanapali Beach 723

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $849 to $1,169/night

  28. CONDOMINIUM
    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $849 to $1,169/night

  29. CONDOMINIUM
    MAKENA SURF RESORT, #B-204

    MAKENA SURF RESORT, #B-204

    Makena, Maui, HI

    Pool Hot Tub

    $841 to $1,319/night

  30. CONDOMINIUM
    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    Wailea, Maui, HI

    Pool Hot Tub

    $841 to $1,515/night

  31. CONDOMINIUM
    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    Wailea, Maui, HI

    Pool Hot Tub

    $785 to $1,347/night

  32. CONDOMINIUM
    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    Wailea, Maui,, HI

    Pool Hot Tub

    $785 to $1,347/night

  33. CONDOMINIUM
    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua, HI

    $781 to $1,219/night

  34. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $781 to $1,219/night

  35. CONDOMINIUM
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    Pool

    $781 to $1,219/night

  36. CONDOMINIUM
    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  37. CONDOMINIUM
    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  38. CONDOMINIUM
    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  39. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  40. CONDOMINIUM
    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    Makena, Maui, HI

    Pool Hot Tub

    $762 to $1,094/night

  41. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  42. 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 $934/night

  43. CONDOMINIUM
    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    Makena, Maui, HI

    Pool Hot Tub

    $751 to $1,319/night

  44. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  45. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $739 to $1,723/night

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

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

    Kamuela, HI

    Pool Hot Tub

    $737 to $2,171/night

  47. CONDOMINIUM
    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  48. CONDOMINIUM
    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  49. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  50. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

  51. HOUSE
    WAILEA ELUA, #1309

    WAILEA ELUA, #1309

    Wailea, Maui, HI

    Pool Hot Tub

    $634 to $896/night

  52. HOUSE
    Koa Kai Hale

    Koa Kai Hale

    Princeville, HI

    $631 to $1,233/night

  53. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  54. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  55. 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 $1,654/night

  56. CONDOMINIUM
    WAILEA ELUA, #2204*

    WAILEA ELUA, #2204*

    Wailea, Maui, HI

    Pool Hot Tub

    $616 to $1,065/night

  57. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,325/night

  58. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  59. CONDOMINIUM
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $602 to $764/night

  60. CONDOMINIUM
    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua, HI

    Pool

    $594 to $969/night

  61. CONDOMINIUM
    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    Lahaina, HI

    Pool

    $594 to $1,063/night

  62. CONDOMINIUM
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    Pool

    $594 to $1,063/night

  63. HOUSE
    Koana Breeze

    Koana Breeze

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION
  64. CONDOMINIUM
    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    Makena, Maui, HI

    Pool Hot Tub

    $583 to $926/night

  65. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  66. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $571 to $1,789/night

  67. CONDOMINIUM
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  68. CONDOMINIUM
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    Pool

    $563 to $781/night

  69. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  70. CONDOMINIUM
    MAKENA SURF RESORT, #F-209

    MAKENA SURF RESORT, #F-209

    Makena, Maui, HI

    Pool Hot Tub

    $560 to $1,094/night

  71. CONDOMINIUM
    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Pool

    $556 to $1,063/night

  72. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $551 to $922/night

  73. CONDOMINIUM
    MAKENA SURF RESORT, #C-106

    MAKENA SURF RESORT, #C-106

    Makena, Maui, HI

    Pool Hot Tub

    $549 to $926/night

  74. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  75. CONDOMINIUM
    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    Makena, Maui, HI

    Pool Hot Tub

    $549 to $926/night

  76. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  77. CONDOMINIUM
    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  78. CONDOMINIUM
    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    Kapalua Ridge Villa 922 Ocean View 2 bed 3 bath

    Kapalua, HI

    Pool

    $525 to $869/night

  79. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  80. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,174/night

  81. CONDOMINIUM
    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua, HI

    Pool

    $525 to $869/night

  82. CONDOMINIUM
    Kapalua Ridge Villa 1523 Gold Ocean View

    Kapalua Ridge Villa 1523 Gold Ocean View

    Kapalua, HI

    Pool

    $525 to $906/night

  83. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  84. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Pool
    FREE CANCELLATION

    $520 to $581/night

  85. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  86. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,325/night

  87. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $513 to $977/night

  88. CONDOMINIUM
    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,673/night

  89. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,789/night

  90. CONDOMINIUM
    Pili Mai 8D

    Pili Mai 8D

    Koloa, HI

    Pool Hot Tub

    $512 to $1,062/night

  91. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,789/night

  92. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $508 to $988/night

  93. HOUSE
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Pool Hot Tub

    $506 to $2,069/night

  94. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  95. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  96. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  97. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

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

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

    Honolulu, HI

    Hot Tub Pets OK
    FREE CANCELLATION

    $504 to $1,287/night

  99. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  100. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night