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. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  2. $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
  3. $138 to $277/night

    Kihei Bay Surf #250

    Kihei Bay Surf #250

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  5. $244 to $412/night

    Grand Champions #51

    Grand Champions #51

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $278 to $454/night

    Palms at Wailea #604

    Palms at Wailea #604

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $229 to $409/night

    Maui Kamaole #A-102

    Maui Kamaole #A-102

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $227 to $340/night

    Maui Sunset #A-117

    Maui Sunset #A-117

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $218 to $389/night

    Maui Sunset #A-509

    Maui Sunset #A-509

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $458 to $748/night

    Grand Champions #143

    Grand Champions #143

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $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
  13. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $180 to $342/night

    Luana Kai #A-205

    Luana Kai #A-205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $126 to $231/night

    Kihei Bay Vista #A-201

    Kihei Bay Vista #A-201

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  16. $229 to $409/night

    Maui Kamaole #G-101

    Maui Kamaole #G-101

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $115 to $186/night

    Kihei Bay Surf #213

    Kihei Bay Surf #213

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $191 to $347/night

    Maui Kamaole #J-120

    Maui Kamaole #J-120

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $226 to $336/night

    Maui Kamaole #J-217

    Maui Kamaole #J-217

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $405 to $579/night

    Palms at Wailea #1507

    Palms at Wailea #1507

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  22. $270 to $341/night

    Pali Ke Kua #204

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  23. $456 to $652/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  24. $258 to $488/night

    Vista Waikoloa B-302

    Vista Waikoloa B-302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $229 to $407/night

    Maui Kamaole #B-206

    Maui Kamaole #B-206

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $194 to $346/night

    Kamaole Sands #10-111

    Kamaole Sands #10-111

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $680 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $257 to $308/night

    Plantation at Princeville 1322

    Plantation at Princeville 1322

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $159 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $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
  31. $103 to $173/night

    Kihei Bay Surf #253

    Kihei Bay Surf #253

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $362 to $646/night

    Palms at Wailea #2303

    Palms at Wailea #2303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $274 to $521/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $230 to $336/night

    Villas of Kamalii 37

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $289 to $493/night

    Palms at Wailea #1101

    Palms at Wailea #1101

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $126 to $231/night

    Kihei Bay Vista #A-103

    Kihei Bay Vista #A-103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $121 to $219/night

    Kihei Bay Vista #D-208

    Kihei Bay Vista #D-208

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $681 to $1,717/night

    Wailea Elua #2303

    Wailea Elua #2303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $158 to $244/night

    Pacific Shores #A-101

    Pacific Shores #A-101

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $386 to $690/night

    Palms at Wailea #1102

    Palms at Wailea #1102

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $556 to $927/night

    Hale Ili Ili #D

    Hale Ili Ili #D

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $458 to $725/night

    Wailea Elua #2110

    Wailea Elua #2110

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $302 to $418/night

    Maui Kamaole #F-207

    Maui Kamaole #F-207

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $180 to $209/night

    Shores of Maui #124

    Shores of Maui #124

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $254 to $452/night

    Grand Champions #48

    Grand Champions #48

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $208 to $335/night

    Shores of Maui #211

    Shores of Maui #211

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $204 to $413/night

    Maui Kamaole #K-108

    Maui Kamaole #K-108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $219 to $360/night

    Maui Kamaole #F-210

    Maui Kamaole #F-210

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $208 to $347/night

    Maui Kamaole #K-209

    Maui Kamaole #K-209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $174 to $347/night

    Maui Kamaole #I-109

    Maui Kamaole #I-109

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $175 to $614/night

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $324 to $486/night

    Maui Kamaole #J-219

    Maui Kamaole #J-219

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $241 to $329/night

    Pali Ke Kua #241

    Pali Ke Kua #241

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  54. $375 to $459/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  55. $234 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $103 to $173/night

    Kihei Bay Surf #123

    Kihei Bay Surf #123

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $303 to $538/night

    Palms at Wailea #1005

    Palms at Wailea #1005

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $262 to $464/night

    Kamaole Sands #7-408

    Kamaole Sands #7-408

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $695 to $1,043/night

    Hale Ili Ili #A

    Hale Ili Ili #A

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $226 to $257/night

    Alii Kai II 11B

    Alii Kai II 11B

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $218 to $389/night

    Grand Champions #151

    Grand Champions #151

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $302 to $458/night

    Maui Kamaole #A-203

    Maui Kamaole #A-203

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $428 to $579/night

    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $262 to $462/night

    Palms at Wailea #702

    Palms at Wailea #702

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $173 to $381/night

    Noelani #219

    Noelani #219

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $196 to $273/night

    Kamaole Sands #9-207

    Kamaole Sands #9-207

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $216 to $348/night

    Kamaole Sands #10-312

    Kamaole Sands #10-312

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $234 to $464/night

    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $282 to $502/night

    Palms at Wailea #603

    Palms at Wailea #603

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $115 to $196/night

    Kihei Garden Estates #A-102

    Kihei Garden Estates #A-102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $347 to $521/night

    Palms at Wailea #1105

    Palms at Wailea #1105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $133 to $360/night

    Kamaole Sands #5-103

    Kamaole Sands #5-103

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $162 to $401/night

    Kolepa Aloha

    Kolepa Aloha

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  74. $330 to $689/night

    Big Island Paradise

    Big Island Paradise

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  75. $259 to $335/night

    Plantations at Princeville #1122

    Plantations at Princeville #1122

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  76. $259 to $361/night

    Plantations at Princeville #521

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  77. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  78. $237 to $359/night

    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    3 Bedrooms2.5 BathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $145 to $244/night

    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $371 to $514/night

    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  81. $175 to $183/night

    Villas on the Prince 34

    Villas on the Prince 34

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool Hot Tub
    FREE CANCELLATION