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. $146 to $158/night

    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  3. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  4. $1,797 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  5. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $179 to $258/night

    Waikiki Banyan Tower 2 Suite 2904- QP

    Waikiki Banyan Tower 2 Suite 2904- QP

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $234 to $476/night

    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  9. $156 to $296/night

    Hale Ono Loa 401

    Hale Ono Loa 401

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $339 to $717/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  12. $455 to $1,035/night

    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  13. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $361 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  15. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  16. $456 to $616/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  17. $310 to $535/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  18. $250 to $598/night

    Palm Leaf

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  19. $241 to $244/night

    Country Club Villas#115

    Country Club Villas#115

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $121 to $156/night

    Sandpiper 121B

    Sandpiper 121B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $249 to $499/night

    Kaanapali Royal G102

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $438 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $211 to $324/night

    Napili Shores E243

    Napili Shores E243

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $201 to $574/night

    Kona Nalu #302

    Kona Nalu #302

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $61 to $269/night

    Kona Bali Kai Studio w/ Pool & Spa

    Kona Bali Kai Studio w/ Pool & Spa

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $493 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  28. $192 to $234/night

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $625 to $1,648/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $169 to $300/night

    Eldorado E104

    Eldorado E104

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  33. $188 to $260/night

    Paki Maui 316

    Paki Maui 316

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $234 to $311/night

    Pacific Shores B406

    Pacific Shores B406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $194 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $503 to $649/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $275 to $466/night

    Eldorado K203

    Eldorado K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $313 to $438/night

    Maui Banyan Q204

    Maui Banyan Q204

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $200 to $301/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  41. $526 to $860/night

    Papakea K-402

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $304 to $436/night

    Honua Kai 1024

    Honua Kai 1024

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $357 to $741/night

    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $243 to $433/night

    Aina Nalu B204

    Aina Nalu B204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $397 to $1,209/night

    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  47. $411 to $947/night

    Kona Makai 6301

    Kona Makai 6301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  48. $267 to $568/night

    Kona Makai 6305

    Kona Makai 6305

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
  49. $481 to $899/night

    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  50. $387 to $1,038/night

    Pili Mai 11I

    Pili Mai 11I

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  51. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  52. $899 to $2,407/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  53. $482 to $1,220/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  54. $195 to $299/night

    Napili Shores E240

    Napili Shores E240

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $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
  56. $601 to $1,317/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  57. $363 to $869/night

    Pili Mai 3G

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  58. $279 to $408/night

    Hale Kukui Ola

    Hale Kukui Ola

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Hot Tub
  59. $766 to $2,122/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  60. $386 to $857/night

    Onomea Cliffside Cottage

    Onomea Cliffside Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
  61. $250 to $574/night

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in the Heart

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in th...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  62. $280 to $595/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  63. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  64. $1,131 to $3,225/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  65. $252 to $587/night

    Waikoloa Villas F-100

    Waikoloa Villas F-100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  66. $500 to $1,095/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  67. $413 to $1,012/night

    Casa De Emdeko 338

    Casa De Emdeko 338

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  68. $1,434 to $3,932/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  69. $780 to $1,361/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  70. $1,417 to $5,441/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  71. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $240 to $343/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $379 to $483/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $216 to $407/night

    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $174 to $375/night

    Paki Maui 415

    Paki Maui 415

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $208 to $314/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $689 to $841/night

    Mahana 519

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $490 to $1,673/night

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  80. $173 to $296/night

    Kahana Villa F410

    Kahana Villa F410

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $341 to $413/night

    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $363 to $516/night

    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  83. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $216 to $407/night

    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $136 to $330/night

    Kahala 123

    Kahala 123

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $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
  87. $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
  88. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  89. $420 to $693/night

    Mahana 1113

    Mahana 1113

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $432 to $861/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  93. $571 to $1,789/night

    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  94. $443 to $861/night

    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  95. $508 to $1,789/night

    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  96. $362 to $977/night

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  97. $306 to $358/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $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
  99. $270 to $346/night

    Pali Ke Kua #204

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  100. $246 to $617/night

    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION