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. 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

  4. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  5. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,938 to $4,750/night

  6. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  7. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  8. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  9. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    $1,661 to $2,429/night

  10. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  11. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  12. HOUSE
    Makalae

    Makalae

    Koloa, HI

    $1,303 to $1,404/night

  13. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,253 to $1,395/night

  14. HOUSE
    Lau'lea at the Mauna Lani*

    Lau'lea at the Mauna Lani*

    Kamuela, HI

    Pool Hot Tub

    $1,195 to $4,289/night

  15. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

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

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,160 to $3,417/night

  17. HOUSE
    Pu'uwai Hale

    Pu'uwai Hale

    Princeville, HI

    $1,152 to $1,645/night

  18. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,605/night

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

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $996 to $3,148/night

  20. HOUSE
    Punahele Point

    Punahele Point

    Princeville, HI

    $978 to $1,192/night

  21. 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

    $943 to $2,939/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

    $923 to $3,081/night

  23. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,267/night

  24. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $863 to $3,547/night

  25. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  26. HOUSE
    Hale Pulelehua TVNC#1238

    Hale Pulelehua TVNC#1238

    Hanalei, HI

    $809 to $1,729/night

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

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

    Kailua Kona, HI

    Pool

    $809 to $2,505/night

  28. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  29. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  30. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $1,910/night

  31. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  32. 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

  33. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $2,110/night

  34. HOUSE
    Malapua

    Malapua

    Hanalei, HI

    FREE CANCELLATION

    $748 to $1,060/night

  35. HOUSE
    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    Kamuela, HI

    Pool Hot Tub

    $706 to $2,141/night

  36. HOUSE
    Ohana Kamalani

    Ohana Kamalani

    Princeville, HI

    Pool

    $690 to $1,661/night

  37. HOUSE
    Lokelani Hale

    Lokelani Hale

    Hanalei, HI

    FREE CANCELLATION

    $686 to $873/night

  38. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  39. HOUSE
    Koa Kai Hale

    Koa Kai Hale

    Princeville, HI

    $631 to $1,465/night

  40. 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 $1,651/night

  41. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

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

    Hale Kanani (Kaua'i) TVNC 1342

    Hanalei, HI

    $595 to $1,327/night

  43. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  44. HOUSE
    Pineapple Hale

    Pineapple Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $574 to $1,871/night

  45. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $573 to $1,344/night

  46. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,028/night

  47. HOUSE
    Keauhou Estates #189

    Keauhou Estates #189

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $535 to $1,239/night

  48. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  49. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  50. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  51. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  52. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  53. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  54. VILLA
    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    Waikoloa, HI

    Pool Hot Tub

    $500 to $1,399/night

  55. HOUSE
    Ohana House

    Ohana House

    Hanalei, HI

    FREE CANCELLATION

    $499 to $562/night

  56. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  57. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  58. HOUSE
    Keauhou Estates #185

    Keauhou Estates #185

    Kailua Kona, HI

    Hot Tub

    $482 to $780/night

  59. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  60. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    Pool Hot Tub

    $482 to $839/night

  61. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    Pool Hot Tub

    $481 to $899/night

  62. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,673/night

  63. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  64. CONDOMINIUM
    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $465 to $1,354/night

  65. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    $464 to $1,119/night

  66. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool Hot Tub

    $456 to $659/night

  67. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $572/night

  68. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $452 to $926/night

  69. CONDOMINIUM
    Kahana Sunset A4

    Kahana Sunset A4

    Lahaina, HI

    Pool

    $428 to $484/night

  70. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  71. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  72. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  73. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  74. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    Princeville, HI

    Pool Hot Tub

    $422 to $542/night

  75. HOUSE
    Paradise Bluff

    Paradise Bluff

    Laupahoehoe, HI

    Pool

    $417 to $1,038/night

  76. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $416 to $1,291/night

  77. CONDOMINIUM
    Puu Poa 406

    Puu Poa 406

    Princeville, HI

    Pool

    $416 to $512/night

  78. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    Pool Hot Tub

    $393 to $1,044/night

  79. CONDOMINIUM
    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    Koloa, HI

    Pool Hot Tub

    $392 to $514/night

  80. CONDOMINIUM
    Puu Poa 310

    Puu Poa 310

    Princeville, HI

    Pool

    $392 to $542/night

  81. BUNGALOW
    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    Kailua Kona, HI

    $375 to $720/night

  82. CONDOMINIUM
    Kona Reef #D22

    Kona Reef #D22

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $375 to $1,296/night

  83. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  84. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $366 to $501/night

  85. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $364 to $1,219/night

  86. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $988/night

  87. CONDOMINIUM
    Pali Ke Kua 121

    Pali Ke Kua 121

    Princeville, HI

    Pool Hot Tub

    $362 to $422/night

  88. CONDOMINIUM
    Puu Poa 207

    Puu Poa 207

    Princeville, HI

    Pool

    $362 to $512/night

  89. CONDOMINIUM
    Pali Ke Kua 203

    Pali Ke Kua 203

    Princeville, HI

    Pool Hot Tub

    $362 to $422/night

  90. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $361 to $479/night

  91. CONDOMINIUM
    Pali Ke Kua #103

    Pali Ke Kua #103

    Princeville, HI

    Pool Hot Tub

    $349 to $456/night

  92. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  93. APARTMENT
    Kolea 14F at the Waikoloa Beach Resort

    Kolea 14F at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $344 to $1,059/night

  94. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $344 to $1,059/night

  95. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  96. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  97. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  98. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  99. CONDOMINIUM
    Turtle Bay Hanalei***TA-147868876801

    Turtle Bay Hanalei***TA-147868876801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  100. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night