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

    $4,524 to $5,243/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

    $2,540 to $5,568/night

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

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

    Kamuela, HI

    Pool

    $2,505 to $4,766/night

  7. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  8. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  9. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  10. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

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

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

    Kihei, HI

    $1,618 to $26,094/night

  12. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

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

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

    Kamuela, HI

    Pool Hot Tub

    $1,373 to $4,071/night

  14. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    Pool Hot Tub

    $1,372 to $2,014/night

  15. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,257 to $1,395/night

  16. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  17. ESTATE
    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $1,188 to $3,185/night

  18. CONDOMINIUM
    The Montage Kapalua Bay- Heliconia 2302- Ocean View Paradise!

    The Montage Kapalua Bay- Heliconia 2302- Ocean View Para...

    Kapalua, HI

    Pool Hot Tub

    $1,187 to $3,316/night

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

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,182 to $3,546/night

  20. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  21. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  22. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,166 to $3,653/night

  23. HOUSE
    Pu'uwai Hale

    Pu'uwai Hale

    Princeville, HI

    $1,152 to $1,645/night

  24. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  25. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,139 to $1,535/night

  26. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Pool Hot Tub

    $1,137 to $2,029/night

  27. HOUSE
    Ke Kailani Hale A2

    Ke Kailani Hale A2

    Waikoloa, HI

    Pool Hot Tub

    $1,137 to $2,743/night

  28. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $1,082 to $3,365/night

  29. 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

    $1,060 to $3,293/night

  30. VILLA
    Mauna Kea Villas #13

    Mauna Kea Villas #13

    Kamuela, HI

    $1,018 to $1,880/night

  31. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

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

    Kailua Kona, HI

    Pool Hot Tub

    $970 to $2,858/night

  32. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    Pool

    $958 to $1,375/night

  33. HOUSE
    Hale Pulelehua with Guest House TVNC#1238

    Hale Pulelehua with Guest House TVNC#1238

    Hanalei, HI

    $952 to $2,635/night

  34. 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

    $923 to $2,944/night

  35. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,487/night

  36. CONDOMINIUM
    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    Kamuela, HI

    Pool Hot Tub

    $899 to $1,553/night

  37. HOUSE
    Hale Poola

    Hale Poola

    Honolulu, HI

    $890 to $1,302/night

  38. CONDOMINIUM
    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3.5b

    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3....

    Kaanapali, HI

    Pool Hot Tub

    $886 to $3,261/night

  39. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $825 to $2,810/night

  40. HOUSE
    Hale Pulelehua TVNC#1238

    Hale Pulelehua TVNC#1238

    Hanalei, HI

    $797 to $2,222/night

  41. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  42. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $781 to $1,219/night

  43. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $2,199/night

  44. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION
  45. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,677/night

  46. HOUSE
    Malapua

    Malapua

    Hanalei, HI

    FREE CANCELLATION

    $748 to $1,060/night

  47. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Pool

    $744 to $2,569/night

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

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,016/night

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

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

    Kailua Kona, HI

    Pool

    $720 to $2,118/night

  50. HOUSE
    Hale Koaniani

    Hale Koaniani

    Wainiha, HI

    FREE CANCELLATION

    $717 to $904/night

  51. 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

    $706 to $2,171/night

  52. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  53. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $688 to $759/night

  54. HOUSE
    Hale A Kai

    Hale A Kai

    Princeville, HI

    FREE CANCELLATION

    $686 to $936/night

  55. HOUSE
    Lokelani Hale

    Lokelani Hale

    Hanalei, HI

    FREE CANCELLATION

    $686 to $873/night

  56. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

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

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  58. HOUSE
    Milo Hae Hale

    Milo Hae Hale

    Koloa, HI

    Pool

    $661 to $1,854/night

  59. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $632 to $1,015/night

  60. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    Hot Tub

    $631 to $1,693/night

  61. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  62. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  63. 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

  64. HOUSE
    Hale Kalani

    Hale Kalani

    Wainiha, HI

    FREE CANCELLATION

    $623 to $748/night

  65. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Pool Hot Tub

    $616 to $2,355/night

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

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,668/night

  67. HOUSE
    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Honolulu, HI

    FREE CANCELLATION

    $606 to $883/night

  68. HOUSE
    Koa Kai Hale

    Koa Kai Hale

    Princeville, HI

    $601 to $1,227/night

  69. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Pool Hot Tub

    $595 to $1,227/night

  70. HOUSE
    Hale Kanani (Kaua'i) TVNC 1342

    Hale Kanani (Kaua'i) TVNC 1342

    Hanalei, HI

    $595 to $1,611/night

  71. CONDOMINIUM
    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua, HI

    Pool

    $594 to $969/night

  72. CONDOMINIUM
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    Pool

    $594 to $1,063/night

  73. CONDOMINIUM
    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    Lahaina, HI

    Pool

    $594 to $1,063/night

  74. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  75. CONDOMINIUM
    Wailea Ekahi #34-C

    Wailea Ekahi #34-C

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $580 to $783/night

  76. CONDOMINIUM
    Honua kai- Konea 301 Frontline with BBQ!

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $566 to $2,227/night

  77. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

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

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $559 to $1,784/night

  79. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Pool

    $559 to $1,993/night

  80. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  81. CONDOMINIUM
    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $550 to $1,558/night

  82. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  83. 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

    $549 to $1,411/night

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

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Pool Hot Tub

    $548 to $2,016/night

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

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Pool Hot Tub

    $548 to $2,016/night

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

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  87. HOUSE
    Hoku'Ea Hale

    Hoku'Ea Hale

    Kailua Kona, HI

    Hot Tub

    $545 to $2,136/night

  88. HOUSE
    Kiahuna Plantation Hale

    Kiahuna Plantation Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  89. HOUSE
    Honu O Kai (Turtle of the Sea)

    Honu O Kai (Turtle of the Sea)

    Kailua Kona, HI

    Pool

    $542 to $1,924/night

  90. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  91. HOUSE
    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    Koloa, HI

    Pool Hot Tub

    $542 to $1,421/night

  92. CONDOMINIUM
    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $538 to $1,962/night

  93. CONDOMINIUM
    Bali Hai Villas 3 Bedroom

    Bali Hai Villas 3 Bedroom

    Princeville, HI

    Pool Hot Tub
  94. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Kaanapali, HI

    Pool Hot Tub

    $531 to $1,999/night

  95. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  96. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Pool

    $530 to $780/night

  97. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  98. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,174/night

  99. CONDOMINIUM
    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua, HI

    Pool

    $525 to $869/night

  100. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Pool
    FREE CANCELLATION

    $520 to $581/night