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. $217 to $623/night

    Aina Nalu C108

    Aina Nalu C108

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $217 to $623/night

    Aina Nalu C102

    Aina Nalu C102

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $158 to $191/night

     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $345/night

    Turtle Bay Sugar Cane***

    Turtle Bay Sugar Cane***

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  5. $191/night

    Turtle Bay Sea Shells**TA-154567065601

    Turtle Bay Sea Shells**TA-154567065601

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $271/night

    Turtle Bay Morning Glory***TA-147878707201

    Turtle Bay Morning Glory***TA-147878707201

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $271/night

    Turtle Bay Hale Lani***TA-030645555201

    Turtle Bay Hale Lani***TA-030645555201

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $202 to $636/night

    Aina Nalu Condo A209

    Aina Nalu Condo A209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  9. $202 to $636/night

    Aina Nalu Condo B103

    Aina Nalu Condo B103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  10. $202 to $636/night

    Aina Nalu Condo C208

    Aina Nalu Condo C208

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $231 to $618/night

    Lahaina Condo K202

    Lahaina Condo K202

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  12. $231 to $618/night

    Lahaina Condo J209

    Lahaina Condo J209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  13. $231 to $618/night

    Aina Nalu Condo K107

    Aina Nalu Condo K107

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  14. $322 to $435/night

    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  15. $190 to $623/night

    Aina Nalu Premier Condo B108

    Aina Nalu Premier Condo B108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  16. $173 to $348/night

    Maui Vista #2-402

    Maui Vista #2-402

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  17. $350 to $861/night

    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  18. $184 to $409/night

    Pohailani #133

    Pohailani #133

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  19. $228 to $437/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $273 to $405/night

    Palms at Wailea #1501

    Palms at Wailea #1501

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $217 to $604/night

    Aina Nalu Premier Condo G108

    Aina Nalu Premier Condo G108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $249 to $348/night

    Hale Kamaole #318

    Hale Kamaole #318

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  23. $296 to $521/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  25. $157 to $277/night

    Waiohuli Beach Hale #D-122

    Waiohuli Beach Hale #D-122

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. $220 to $470/night

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  27. $157 to $289/night

    Kamaole Sands #8-310

    Kamaole Sands #8-310

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $126 to $231/night

    Kihei Bay Vista #C-205

    Kihei Bay Vista #C-205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $244 to $383/night

    Palms at Wailea #1604

    Palms at Wailea #1604

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $261 to $347/night

    Wailea Ekolu #407

    Wailea Ekolu #407

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  31. $274 to $521/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  32. $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
  33. $150 to $242/night

    Kihei Akahi #C-217

    Kihei Akahi #C-217

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $133 to $244/night

    Kihei Kai Nani #12-136

    Kihei Kai Nani #12-136

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $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
  36. $231 to $331/night

    Hale Kamaole #101

    Hale Kamaole #101

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  37. $146 to $363/night

    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  38. $157 to $277/night

    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  39. $196 to $377/night

    Maui Banyan #B-204

    Maui Banyan #B-204

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $312 to $428/night

    Wailea Ekolu #1608

    Wailea Ekolu #1608

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  41. $168 to $278/night

    Kamaole Sands #1-103

    Kamaole Sands #1-103

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  43. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  44. $219 to $394/night

    Palms at Wailea #2305

    Palms at Wailea #2305

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $416 to $664/night

    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  46. $364 to $608/night

    Palm Villas F4 at Mauna Lani Resort

    Palm Villas F4 at Mauna Lani Resort

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  47. $307 to $522/night

    Wailea Ekolu #205

    Wailea Ekolu #205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $219 to $348/night

    Maui Vista #3-404

    Maui Vista #3-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  49. $158 to $244/night

    Pacific Shores #A-101

    Pacific Shores #A-101

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $133 to $244/night

    Kihei Garden Estates #E-102

    Kihei Garden Estates #E-102

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $556 to $927/night

    Hale Ili Ili #D

    Hale Ili Ili #D

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $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
  53. $458 to $725/night

    Wailea Elua #2110

    Wailea Elua #2110

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $302 to $418/night

    Maui Kamaole #F-207

    Maui Kamaole #F-207

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $157 to $277/night

    Waiohuli Beach Hale #B-108

    Waiohuli Beach Hale #B-108

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. $284 to $435/night

    Wailea Ekahi #45-E

    Wailea Ekahi #45-E

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  57. $347 to $695/night

    Maui Hill #I-99

    Maui Hill #I-99

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $290 to $487/night

    Wailea Ekolu #201

    Wailea Ekolu #201

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $178 to $610/night

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  61. $208 to $335/night

    Shores of Maui #211

    Shores of Maui #211

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $273 to $463/night

    Wailea Ekolu #1207

    Wailea Ekolu #1207

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  63. $162 to $324/night

    Kanai A Nalu #311

    Kanai A Nalu #311

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  64. $231 to $618/night

    Lahaina Condo D203

    Lahaina Condo D203

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  65. $133 to $226/night

    Kihei Garden Estates #B-201

    Kihei Garden Estates #B-201

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $284 to $405/night

    Maui Kamaole #H-211

    Maui Kamaole #H-211

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $126 to $231/night

    Kihei Akahi #D-112

    Kihei Akahi #D-112

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $164 to $183/night

    Villas on the Prince 28

    Villas on the Prince 28

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
    FREE CANCELLATION
  69. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  70. $204 to $413/night

    Maui Kamaole #K-108

    Maui Kamaole #K-108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $219 to $360/night

    Maui Kamaole #F-210

    Maui Kamaole #F-210

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $208 to $347/night

    Maui Kamaole #K-209

    Maui Kamaole #K-209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $244 to $463/night

    Maui Kamaole #J-221

    Maui Kamaole #J-221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $231 to $377/night

    Maui Kamaole #I-215

    Maui Kamaole #I-215

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $174 to $347/night

    Maui Kamaole #I-109

    Maui Kamaole #I-109

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $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
  77. $261 to $464/night

    Grand Champions #65

    Grand Champions #65

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $194 to $431/night

    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $221 to $431/night

    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $174 to $445/night

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $249 to $481/night

    Wailea Ekolu #805

    Wailea Ekolu #805

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. $157 to $277/night

    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  83. $324 to $486/night

    Maui Kamaole #J-219

    Maui Kamaole #J-219

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $241 to $329/night

    Pali Ke Kua #241

    Pali Ke Kua #241

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  85. $311 to $429/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  86. $375 to $459/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  87. $206 to $333/night

    Plantations at Princeville #111

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  88. $234 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $118 to $263/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $157 to $277/night

    Waiohuli Beach Hale #B-206

    Waiohuli Beach Hale #B-206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  91. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  92. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  93. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $247 to $488/night

    Vista Waikoloa B-302

    Vista Waikoloa B-302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $274 to $521/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  97. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $161 to $266/night

    Kauhale Makai #330

    Kauhale Makai #330

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $231 to $347/night

    Wailea Ekolu #911

    Wailea Ekolu #911

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  100. $297 to $448/night

    Maui Kamaole #H-205

    Maui Kamaole #H-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION