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. $174 to $289/night

    Kamaole Sands #8-208

    Kamaole Sands #8-208

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $180 to $335/night

    Kihei Garden Estates #H-203

    Kihei Garden Estates #H-203

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $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
  6. $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
  7. $136 to $286/night

    Napili Shores D230

    Napili Shores D230

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  11. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  12. $513 to $988/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  14. $218 to $389/night

    Maui Sunset #A-509

    Maui Sunset #A-509

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  16. $377 to $493/night

    Maui Kamaole #G-210

    Maui Kamaole #G-210

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $180 to $342/night

    Luana Kai #A-205

    Luana Kai #A-205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $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
  19. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  22. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $231 to $371/night

    Maalaea Banyans #403

    Maalaea Banyans #403

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $157 to $371/night

    Kamaole Sands #4-105

    Kamaole Sands #4-105

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $238 to $598/night

    Palm Leaf

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  26. $256 to $577/night

    Aina Nalu B204

    Aina Nalu B204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $150 to $433/night

    Eldorado E104

    Eldorado E104

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $199 to $434/night

    Kahana Sunset C1

    Kahana Sunset C1

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $168 to $258/night

    Waikiki Banyan Tower 2 Suite 2904- STQP

    Waikiki Banyan Tower 2 Suite 2904- STQP

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $199 to $499/night

    Kaanapali Royal G102

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $157 to $244/night

    Kihei Garden Estates #E-204

    Kihei Garden Estates #E-204

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $119 to $300/night

    Paki Maui 316

    Paki Maui 316

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  34. $246 to $476/night

    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $196 to $342/night

    Maui Kamaole #J-103

    Maui Kamaole #J-103

    1 BedroomBathroomsSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $356 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $334 to $556/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  38. $270 to $341/night

    Pali Ke Kua #204

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  39. $340 to $503/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  40. $525 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $234 to $407/night

    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $341 to $413/night

    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $136 to $375/night

    Paki Maui 415

    Paki Maui 415

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $273 to $429/night

    Kamaole Sands #5-414

    Kamaole Sands #5-414

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $234 to $407/night

    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $226 to $336/night

    Maui Kamaole #J-217

    Maui Kamaole #J-217

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $191 to $347/night

    Maui Kamaole #J-120

    Maui Kamaole #J-120

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $211 to $339/night

    Maui Kamaole #M-105

    Maui Kamaole #M-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $393 to $544/night

    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $370 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
  51. $180 to $324/night

    Napili Shores E243

    Napili Shores E243

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $241 to $244/night

    Country Club Villas#115

    Country Club Villas#115

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  54. $218 to $383/night

    Kamaole Sands #10-205

    Kamaole Sands #10-205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $103 to $173/night

    Kihei Bay Surf #208

    Kihei Bay Surf #208

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $219 to $391/night

    Maui Kamaole #G-107

    Maui Kamaole #G-107

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $240 to $432/night

    Kamaole Sands #7-305

    Kamaole Sands #7-305

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $206 to $363/night

    Maui Sunset #A-407

    Maui Sunset #A-407

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $229 to $409/night

    Maui Kamaole #G-101

    Maui Kamaole #G-101

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $317 to $565/night

    Maui Kamaole #A-201

    Maui Kamaole #A-201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $261 to $455/night

    Kamaole Sands #3-402

    Kamaole Sands #3-402

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $115 to $186/night

    Kihei Bay Surf #213

    Kihei Bay Surf #213

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $254 to $452/night

    Grand Champions #45

    Grand Champions #45

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $227 to $340/night

    Maui Sunset #A-117

    Maui Sunset #A-117

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $350 to $606/night

    Palms at Wailea #2205

    Palms at Wailea #2205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  67. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  68. $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
  69. $138 to $231/night

    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $282 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  71. $282 to $528/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  72. $363 to $528/night

    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  73. $456 to $652/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  74. $269 to $500/night

    Eldorado K203

    Eldorado K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $174 to $238/night

    Maui Kamaole #D-107

    Maui Kamaole #D-107

    1 BedroomBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $173 to $365/night

    Kamaole Sands #7-304

    Kamaole Sands #7-304

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $126 to $231/night

    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $138 to $277/night

    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $138 to $256/night

    Kihei Bay Surf #110

    Kihei Bay Surf #110

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $138 to $277/night

    Kihei Bay Surf #109

    Kihei Bay Surf #109

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $302 to $517/night

    Kamaole Sands #7-403

    Kamaole Sands #7-403

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $275 to $413/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $181 to $399/night

    Aina Nalu K102

    Aina Nalu K102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $124 to $264/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $166 to $441/night

    Kaanapali Shores 546

    Kaanapali Shores 546

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $161 to $448/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $124 to $394/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  91. $1,094 to $3,320/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
  92. $287 to $683/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  93. $250 to $553/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
  94. $132 to $360/night

    Pono Kai H207

    Pono Kai H207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $255 to $675/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $194 to $424/night

    Mahana 602

    Mahana 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $181 to $621/night

    Eldorado H107

    Eldorado H107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $149 to $299/night

    Napili Shores E240

    Napili Shores E240

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $173 to $208/night

    Kamaole Sands #9-203

    Kamaole Sands #9-203

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $899 to $2,267/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub