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. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $134 to $213/night

    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    2 BedroomsBathroomsSleeps 4
    12 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $177 to $225/night

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $140 to $280/night

    Bamboo 610 Studio Apartment

    Bamboo 610 Studio Apartment

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $456 to $594/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  7. $226 to $263/night

    Alii Kai II 8H

    Alii Kai II 8H

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $246 to $464/night

    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $257 to $306/night

    Plantation at Princeville 1322

    Plantation at Princeville 1322

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $216 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $221 to $431/night

    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $230 to $336/night

    Villas of Kamalii 37

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $228 to $409/night

    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $188 to $321/night

    Maui Kai 108

    Maui Kai 108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $220 to $238/night

    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $300 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $344 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $226 to $344/night

    Papakea A309

    Papakea A309

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  21. $505 to $711/night

    Papakea A404

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  22. $249 to $368/night

    Papakea A108

    Papakea A108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  23. $113 to $324/night

    Marine Surf Waikiki 908

    Marine Surf Waikiki 908

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $286 to $478/night

    Hale Ohana Aloha

    Hale Ohana Aloha

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  25. $274 to $448/night

    Kaanapali Royal B303

    Kaanapali Royal B303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $299 to $440/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $199 to $306/night

    Maui Kai 605

    Maui Kai 605

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $247 to $329/night

    Pali Ke Kua #241

    Pali Ke Kua #241

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  29. $424 to $1,125/night

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $375 to $1,354/night

    Kona Reef #D22

    Kona Reef #D22

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $250 to $704/night

    Fairway Villas L21 at the Waikoloa Beach Resort

    Fairway Villas L21 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $194 to $648/night

    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $179 to $521/night

    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $213 to $635/night

    Banyan Tree #305

    Banyan Tree #305

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  35. $250 to $535/night

    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $150 to $451/night

    Kona Makai #6302

    Kona Makai #6302

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $126 to $350/night

    Keauhou Punahele #D103

    Keauhou Punahele #D103

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $178 to $536/night

    Kona Bali Kai #415

    Kona Bali Kai #415

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $280 to $835/night

    KAUHALE MAKAI #532

    KAUHALE MAKAI #532

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $250 to $535/night

    Fairway Villas I34 at the Waikoloa Beach Resort

    Fairway Villas I34 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $218 to $676/night

    Mauna Lani Fairways #803

    Mauna Lani Fairways #803

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $226 to $776/night

    Kanaloa 2201

    Kanaloa 2201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $113 to $374/night

    Marine Surf Waikiki 2108

    Marine Surf Waikiki 2108

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $193 to $536/night

    Sea Village #4210

    Sea Village #4210

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $119 to $353/night

    White Sands Village #309

    White Sands Village #309

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $130 to $480/night

    Sea Village #4202

    Sea Village #4202

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $548 to $919/night

    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  48. $159 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $256 to $345/night

    Kaanapali Shores 936

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $208 to $269/night

    Kamaole Sands 8-203

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $208 to $338/night

    Papakea J103

    Papakea J103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  53. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $274 to $409/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $293 to $356/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $305 to $448/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  59. $249 to $346/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $259 to $394/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $425 to $729/night

    Happy Leilani Hale

    Happy Leilani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $740 to $2,021/night

    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  63. $276 to $370/night

    Honua Kai 322

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $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
  65. $219 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $1,900 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  68. $163 to $313/night

    Kona Makai 2-102

    Kona Makai 2-102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $249 to $368/night

    Papakea A307

    Papakea A307

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  70. $199 to $239/night

    Aina Nalu K 205

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $360 to $421/night

    Kona Makai 3-302

    Kona Makai 3-302

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $274 to $430/night

    Kaanapali Royal E101

    Kaanapali Royal E101

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $365 to $443/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  74. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $516 to $620/night

    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $161 to $274/night

    Kaanapali Shores 628

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $456 to $660/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  78. $205 to $358/night

    Aina Nalu A 201

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $274 to $438/night

    Kahana Sunset E4

    Kahana Sunset E4

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $219 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $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
  84. $118 to $261/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $214 to $238/night

    Cliffs 7303

    Cliffs 7303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $339 to $1,056/night

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $152 to $244/night

    Hawaii Living! Close to Beaches! 2 Bed/2 Bath

    Hawaii Living! Close to Beaches! 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $146 to $183/night

    Perfect for Extended Stays! Two Pools & Two Hot Tubs

    Perfect for Extended Stays! Two Pools & Two Hot Tubs...

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $152 to $286/night

    Exceptional Value for Family! Beautiful Views & Sunsets!

    Exceptional Value for Family! Beautiful Views & Suns...

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $177 to $303/night

    Beautiful Resort! Close to Beaches! Pool & Hot Tub! Fairway Villas N3

    Beautiful Resort! Close to Beaches! Pool & Hot Tub! ...

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $186 to $299/night

    Eldorado J109

    Eldorado J109

    Studio BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $183 to $214/night

    Villas on the Prince 34

    Villas on the Prince 34

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $234 to $464/night

    Vista Waikoloa E-105

    Vista Waikoloa E-105

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $488 to $658/night

    Sands of Kahana 354

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $370 to $901/night

    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $330 to $689/night

    Big Island Paradise

    Big Island Paradise

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  100. $121 to $154/night

    Sandpiper 120B

    Sandpiper 120B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION