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. $167 to $397/night

    Ilikai Tower 1642

    Ilikai Tower 1642

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  2. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $1,797 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  4. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  5. $174 to $484/night

    Ilikai Tower 333

    Ilikai Tower 333

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  6. $150 to $457/night

    Ilikai Tower 2136

    Ilikai Tower 2136

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  7. $157 to $406/night

    Ilikai Tower 633

    Ilikai Tower 633

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  8. $145 to $392/night

    Ilikai Tower 527

    Ilikai Tower 527

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  9. $154 to $429/night

    Ilikai Tower 814

    Ilikai Tower 814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  10. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $1,000 to $2,898/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $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
  13. $599 to $1,386/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  14. $601 to $1,317/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  15. $589 to $1,325/night

    Ho'o Maluhia

    Ho'o Maluhia

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  16. $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
  17. $899 to $2,407/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  18. $1,328 to $3,627/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
  19. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  20. $1,434 to $3,932/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  21. $194 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $200 to $299/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $230 to $445/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $512 to $957/night

    Ono Oasis

    Ono Oasis

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  25. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $141 to $300/night

    Ilikai 1333

    Ilikai 1333

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $240 to $339/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $313 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  30. $240/night

    Keauhou Elima

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool
  31. $766 to $2,122/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  32. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  33. $233 to $344/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $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
  35. $690 to $1,616/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  36. $1,417 to $5,441/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  37. $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
  38. $1,553 to $3,338/night

    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  39. $899 to $1,395/night

    Kona Bubbles

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  40. $307 to $491/night

    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $255 to $455/night

    Kaleialoha 205

    Kaleialoha 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $306 to $419/night

    Kona Bay View House

    Kona Bay View House

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $304 to $366/night

    Eldorado A203

    Eldorado A203

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $161 to $429/night

    Ilikai Tower 634

    Ilikai Tower 634

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  45. $145 to $392/night

    Ilikai Tower 1812

    Ilikai Tower 1812

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  46. $150 to $404/night

    Ilikai Tower 618

    Ilikai Tower 618

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  47. $128 to $329/night

    Ilikai Tower 2121

    Ilikai Tower 2121

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  48. $348 to $921/night

    Ilikai Tower 1934

    Ilikai Tower 1934

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  49. $133 to $349/night

    Ilikai Tower 405

    Ilikai Tower 405

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  50. $710 to $1,875/night

    Pineapple Hale

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $506 to $899/night

    Holua Kai #34

    Holua Kai #34

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  52. $661 to $1,910/night

    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  53. $584 to $1,598/night

    Honu O Kai (Turtle of the Sea)

    Honu O Kai (Turtle of the Sea)

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  54. $306 to $556/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $1,692 to $2,494/night

    Rainbow Hale Estate

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  56. $214 to $319/night

    Kihei Akahi C-616

    Kihei Akahi C-616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $200 to $316/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $200 to $299/night

    Kihei Alii Kai A207

    Kihei Alii Kai A207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  60. $156 to $312/night

    Ilikai 1820

    Ilikai 1820

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $220 to $356/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. $259 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $251 to $384/night

    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  64. $329 to $490/night

    Island Sands 210

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $208 to $310/night

    Island Surf 409

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $162 to $312/night

    Ilikai 1122

    Ilikai 1122

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $278 to $400/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $899 to $1,434/night

    Hale Kauka

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  69. $417 to $756/night

    Hilo Shangrila

    Hilo Shangrila

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  70. $1,373 to $3,444/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
  71. $1,315 to $2,930/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  72. $1,162 to $1,190/night

    Hale Lani

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $245 to $374/night

    Kahana Reef 201

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $744 to $2,192/night

    Blue Hawaii

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  75. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  76. $219 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $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
  78. $2,000 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $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
  80. $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
  81. $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
  82. $542 to $555/night

    Hale Pahukoa

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  83. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $300 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $1,318 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  86. $208 to $250/night

    Hale Kamaole 109

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  88. $348 to $948/night

    Ilikai Tower 2612

    Ilikai Tower 2612

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  89. $138 to $374/night

    Ilikai Tower 613

    Ilikai Tower 613

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  90. $196 to $484/night

    Ilikai Tower 1920

    Ilikai Tower 1920

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  91. $184 to $513/night

    Ilikai Tower 2024

    Ilikai Tower 2024

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  92. $232 to $641/night

    Ilikai Tower 525

    Ilikai Tower 525

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  93. $375 to $789/night

    Ilikai 1243

    Ilikai 1243

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. $631 to $1,534/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  95. $599 to $1,458/night

    Piko Nani

    Piko Nani

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  96. $1,137 to $2,654/night

    Ke Kailani Hale A2

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  97. $542 to $780/night

    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  98. $290 to $626/night

    Lai Nani Oceanfront Estate Bungalow #1

    Lai Nani Oceanfront Estate Bungalow #1

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
  99. $1,266 to $3,944/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  100. $750 to $1,616/night

    Hokulani Villa

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool