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
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  2. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    Pool

    $958 to $1,375/night

  3. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $2,199/night

  4. HOUSE
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Pool

    $423 to $839/night

  5. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $155 to $385/night

  6. CONDOMINIUM
    Ilikai 1122

    Ilikai 1122

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $166 to $262/night

  7. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525 to $642/night

  8. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $150 to $275/night

  9. CONDOMINIUM
    Ilikai 1820

    Ilikai 1820

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $163 to $287/night

  10. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  11. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $467 to $773/night

  12. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,323 to $1,324/night

  13. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $251 to $346/night

  14. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $476/night

  15. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $331/night

  16. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $411/night

  17. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,138 to $1,535/night

  18. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $471/night

  19. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $464/night

  20. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $175 to $445/night

  21. HOUSE
    Hilo Shangrila

    Hilo Shangrila

    Keaau, HI

    Pool Hot Tub

    $417 to $1,096/night

  22. 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 $4,058/night

  23. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Pool

    $744 to $2,772/night

  24. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Pool

    $530 to $780/night

  25. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,677/night

  26. HOUSE
    Milo Hae Hale

    Milo Hae Hale

    Koloa, HI

    Pool

    $661 to $1,854/night

  27. 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

  28. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  29. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  30. HOUSE
    Hale Oliveira

    Hale Oliveira

    Keaau, HI

    Pool

    $346 to $801/night

  31. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $146 to $360/night

  32. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  33. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  34. 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

  35. 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

    $576 to $842/night

  36. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $623/night

  37. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $374/night

  38. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  39. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  40. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  41. HOUSE
    Kilohana Vista

    Kilohana Vista

    Kailua Kona, HI

    Pool

    $555 to $771/night

  42. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  43. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  44. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Pool Hot Tub

    $1,137 to $2,029/night

  45. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759/night

  46. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $183 to $407/night

  47. CONDOMINIUM
    Ilikai 1243

    Ilikai 1243

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $428 to $789/night

  48. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $353/night

  49. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  50. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $437/night

  51. CONDOMINIUM
    Ilikai 1308

    Ilikai 1308

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $164 to $262/night

  52. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $138 to $501/night

  53. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  54. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  55. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $466/night

  56. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $499/night

  57. 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 $2,202/night

  58. BUNGALOW
    Lai Nani Oceanfront Estate Bungalow #1

    Lai Nani Oceanfront Estate Bungalow #1

    Ninole, HI

    Pool

    $279 to $732/night

  59. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    Pool Hot Tub

    $482 to $839/night

  60. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,487/night

  61. HOUSE
    Ono Oasis

    Ono Oasis

    Kailua Kona, HI

    Pool

    $512 to $957/night

  62. 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

  63. 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

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

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  65. HOUSE
    Ohana Kamalani

    Ohana Kamalani

    Princeville, HI

    Pool

    $702 to $1,941/night

  66. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Pool Hot Tub

    $595 to $1,227/night

  67. 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

  68. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $166 to $498/night

  69. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  70. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $813/night

  71. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool

    $689 to $1,678/night

  72. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525/night

  73. CONDOMINIUM
    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $384/night

  74. CONDOMINIUM
    Ilikai 1333

    Ilikai 1333

    Waikiki, HI

    Pool
    FREE CANCELLATION

    $154 to $262/night

  75. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $403/night

  76. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,917 to $5,992/night

  77. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $536/night

  78. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $464/night

  79. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $464/night

  80. BUNGALOW
    Lai Nani Oceanfront Estate Bungalow #2

    Lai Nani Oceanfront Estate Bungalow #2

    Ninole, HI

    Pool Hot Tub

    $279 to $760/night