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
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  2. HOUSE
    Ono Oasis

    Ono Oasis

    Kailua Kona, HI

    Pool

    $512 to $957/night

  3. 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

  4. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Pool Hot Tub

    $601 to $1,077/night

  5. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    Pool Hot Tub

    $482 to $839/night

  6. HOUSE
    Keauhou Estates #189

    Keauhou Estates #189

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $535 to $1,241/night

  7. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $171 to $448/night

  8. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  9. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $268/night

  10. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $345/night

  11. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool
  12. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  13. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $393/night

  14. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  15. CONDOMINIUM
    Kihei Kai Nani 373

    Kihei Kai Nani 373

    Kihei, HI

    Pool
    FREE CANCELLATION

    $134 to $414/night

  16. HOUSE
    Ho'o Maluhia

    Ho'o Maluhia

    Kailua Kona, HI

    Pool

    $496 to $1,692/night

  17. CONDOMINIUM
    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $423/night

  18. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  19. CONDOMINIUM
    Kahana Manor 410

    Kahana Manor 410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $325/night

  20. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    Pool

    $899 to $1,434/night

  21. HOUSE
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Pool

    $506 to $899/night

  22. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  23. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,256 to $1,395/night

  24. HOUSE
    Kona Bay View House

    Kona Bay View House

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $306 to $419/night

  25. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $164 to $345/night

  26. HOUSE
    Pineapple Hale

    Pineapple Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $499 to $1,876/night

  27. CONDOMINIUM
    Papakea B201

    Papakea B201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $385/night

  28. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Pool
    FREE CANCELLATION

    $174 to $419/night

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

    Honu O Kai (Turtle of the Sea)

    Kailua Kona, HI

    Pool

    $547 to $1,924/night

  30. HOUSE
    Hilo Shangrila

    Hilo Shangrila

    Keaau, HI

    Pool Hot Tub

    $417 to $1,132/night

  31. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $401/night

  32. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $243 to $384/night

  33. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $146 to $466/night

  34. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $329/night

  35. 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

  36. CONDOMINIUM
    Royal Kahana 920

    Royal Kahana 920

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $225 to $443/night

  37. CONDOMINIUM
    Eldorado A203

    Eldorado A203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $479/night

  38. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $149 to $404/night

  39. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $407 to $466/night

  40. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525 to $642/night

  41. CONDOMINIUM
    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $320 to $487/night

  42. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,157 to $1,536/night

  43. CONDOMINIUM
    Royal Kahana 308

    Royal Kahana 308

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $423/night

  44. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $389/night

  45. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Pool

    $744 to $2,569/night

  46. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  47. CONDOMINIUM
    Close to the Beach, Shopping and Adventures! 3 Bed Condo

    Close to the Beach, Shopping and Adventures! 3 Bed Condo...

    Kohala Coast, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $426/night

  48. 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

  49. HOUSE
    Milo Hae Hale

    Milo Hae Hale

    Koloa, HI

    Pool

    $690 to $1,361/night

  50. HOUSE
    Hale Oliveira

    Hale Oliveira

    Keaau, HI

    Pool

    $326 to $820/night

  51. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  52. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Pool

    $530 to $780/night

  53. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,767/night

  54. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,605/night

  55. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  56. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $331/night

  57. CONDOMINIUM
    Papakea J107

    Papakea J107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $483/night

  58. CONDOMINIUM
    Kaanapali Shores 836

    Kaanapali Shores 836

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $385/night

  59. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $473 to $883/night

  60. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $189 to $498/night

  61. CONDOMINIUM
    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $491/night

  62. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $305/night

  63. 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

  64. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Pool

    $513 to $1,785/night

  65. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  66. 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

  67. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  68. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  69. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $406/night

  70. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  71. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $275/night

  72. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $304/night

  73. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  74. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $641 to $934/night

  75. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  76. CONDOMINIUM
    Maui Banyan Q306

    Maui Banyan Q306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $130 to $406/night

  77. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  78. HOUSE
    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $219 to $585/night

  79. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $498/night

  80. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  81. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Pool Hot Tub

    $1,137 to $2,029/night

  82. 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

  83. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  84. CONDOMINIUM
    Ilikai 1243

    Ilikai 1243

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $338 to $789/night

  85. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night