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. $375 to $789/night

    Ilikai 1243

    Ilikai 1243

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $184 to $356/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $232 to $658/night

    Ilikai Tower 525

    Ilikai Tower 525

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  4. $827 to $2,367/night

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

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  5. $599 to $1,458/night

    Piko Nani

    Piko Nani

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  6. $420 to $1,076/night

    Kahalu'u Hale

    Kahalu'u Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  7. $534 to $780/night

    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  8. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $4,194 to $7,190/night

    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  10. $1,137 to $2,029/night

    Ali'i Villa

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  11. $576 to $883/night

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

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

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $194 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $625 to $1,585/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  15. $1,314 to $4,289/night

    Lau'lea at the Mauna Lani*

    Lau'lea at the Mauna Lani*

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  16. $425 to $729/night

    Happy Leilani Hale

    Happy Leilani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $223 to $438/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $138 to $343/night

    Kaanapali Shores 936

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $196 to $496/night

    Ilikai Tower 1920

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  20. $184 to $524/night

    Ilikai Tower 2024

    Ilikai Tower 2024

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  21. $1,266 to $3,945/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  22. $174 to $275/night

    Hale Kamaole 109

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $186 to $345/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  25. $210 to $416/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $326 to $713/night

    Hale Oliveira

    Hale Oliveira

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  27. $750 to $2,008/night

    Hokulani Villa

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  28. $290 to $625/night

    Lai Nani Oceanfront Estate Bungalow #1

    Lai Nani Oceanfront Estate Bungalow #1

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
  29. $1,137 to $2,743/night

    Ke Kailani Hale A2

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  30. $348 to $971/night

    Ilikai Tower 2612

    Ilikai Tower 2612

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  31. $290 to $959/night

    Ilikai Tower 1744

    Ilikai Tower 1744

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  32. $138 to $383/night

    Ilikai Tower 613

    Ilikai Tower 613

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  33. $203 to $416/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $161 to $298/night

    Kamaole Sands 8-203

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $198 to $375/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $210 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $152 to $300/night

    Ilikai 1308

    Ilikai 1308

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $278 to $572/night

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

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

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. $1,109/night

    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $210 to $406/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  43. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  44. $2,203 to $4,290/night

    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  45. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $542 to $555/night

    Hale Pahukoa

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  47. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  48. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  49. $1,663 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  50. $211 to $364/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $150 to $469/night

    Ilikai Tower 2136

    Ilikai Tower 2136

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  52. $157 to $415/night

    Ilikai Tower 633

    Ilikai Tower 633

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  53. $1,771 to $5,442/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  54. $601 to $1,317/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  55. $690 to $2,029/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  56. $482 to $720/night

    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  57. $589 to $1,386/night

    Ho'o Maluhia

    Ho'o Maluhia

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  58. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  59. $1,000 to $2,903/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $1,434 to $3,933/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  62. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  63. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $165 to $360/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  66. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  67. $783 to $2,229/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  68. $599 to $1,386/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  69. $512 to $957/night

    Ono Oasis

    Ono Oasis

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  70. $899 to $2,678/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  71. $302 to $652/night

    Lai Nani Oceanfront Estate Bungalow #2

    Lai Nani Oceanfront Estate Bungalow #2

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  72. $1,231 to $3,630/night

    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  73. $145 to $349/night

    Ilikai Tower 333

    Ilikai Tower 333

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  74. $154 to $441/night

    Ilikai Tower 814

    Ilikai Tower 814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  75. $145 to $401/night

    Ilikai Tower 527

    Ilikai Tower 527

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  76. $233 to $345/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  78. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  79. $159 to $318/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $223 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  81. $141 to $300/night

    Ilikai 1333

    Ilikai 1333

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. $161 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $217 to $447/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $115 to $397/night

    Ilikai Tower 1642

    Ilikai Tower 1642

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  85. $2,505 to $4,766/night

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

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

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  86. $240/night

    Keauhou Elima

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool
  87. $206 to $471/night

    Kaleialoha 205

    Kaleialoha 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $274 to $558/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $306 to $419/night

    Kona Bay View House

    Kona Bay View House

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. $174 to $326/night

    Island Surf 409

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  91. $133 to $357/night

    Ilikai Tower 405

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  92. $161 to $441/night

    Ilikai Tower 634

    Ilikai Tower 634

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  93. $1,315 to $2,931/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  94. $661 to $1,910/night

    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  95. $1,373 to $3,451/night

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

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

    4 Bedrooms4.5 BathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
  96. $744 to $2,192/night

    Blue Hawaii

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  97. $899 to $1,434/night

    Hale Kauka

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  98. $636 to $1,875/night

    Pineapple Hale

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $348 to $942/night

    Ilikai Tower 1934

    Ilikai Tower 1934

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  100. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub