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. $188 to $469/night

    Wailea Ekahi 50C

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $218 to $429/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  3. $219 to $431/night

    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $149 to $286/night

    Napili Shores D230

    Napili Shores D230

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $207 to $620/night

    HOL 119

    HOL 119

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $493 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

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

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  10. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  11. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  12. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  13. $191 to $331/night

    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $284 to $615/night

    Kaanapali Shores #916

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $313 to $606/night

    Mahana Resort #1017

    Mahana Resort #1017

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $162 to $354/night

    Papakea #D309

    Papakea #D309

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $186 to $459/night

    Papakea #A105

    Papakea #A105

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $203 to $383/night

    Papakea #C108

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $191 to $408/night

    Lokelani #C104

    Lokelani #C104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $180 to $423/night

    Papakea #D304

    Papakea #D304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $290 to $737/night

    Lahaina Roads #201

    Lahaina Roads #201

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. $383 to $795/night

    Papakea #D402

    Papakea #D402

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $232 to $476/night

    Valley Isle #1203

    Valley Isle #1203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. $336 to $706/night

    Kaanapali Shores #825

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $296 to $580/night

    Papakea #H103

    Papakea #H103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $145 to $302/night

    Papakea #B207

    Papakea #B207

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $191 to $435/night

    Hale Mahina #B303

    Hale Mahina #B303

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $162 to $332/night

    Paki Maui #109

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $122 to $278/night

    Royal Kahana #319

    Royal Kahana #319

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $278 to $640/night

    Lokelani #C205

    Lokelani #C205

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $325 to $638/night

    Mahana Resort #1106

    Mahana Resort #1106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $342 to $661/night

    Mahana Resort #616

    Mahana Resort #616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $157 to $354/night

    Valley Isle #1206

    Valley Isle #1206

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $273 to $447/night

    Lahaina Shores #531

    Lahaina Shores #531

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $209 to $433/night

    Aina Nalu #A109

    Aina Nalu #A109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $232 to $447/night

    Lahaina Shores #425

    Lahaina Shores #425

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $290 to $609/night

    Papakea #G408

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $310 to $574/night

    Kaanapali Royal #N302

    Kaanapali Royal #N302

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $220 to $499/night

    Valley Isle #1103

    Valley Isle #1103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $325 to $580/night

    Papakea #A109

    Papakea #A109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $290 to $638/night

    Papakea #L407

    Papakea #L407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $139 to $302/night

    Valley Isle #107

    Valley Isle #107

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $232 to $414/night

    Lahaina Roads #206

    Lahaina Roads #206

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $278 to $638/night

    Kaanapali Royal #H302

    Kaanapali Royal #H302

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $220 to $464/night

    Hololani #B-403

    Hololani #B-403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $128 to $244/night

    Paki Maui #420

    Paki Maui #420

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  47. $146 to $306/night

    Ilikai 1927

    Ilikai 1927

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. $157 to $312/night

    Ilikai 1904

    Ilikai 1904

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  49. $141 to $300/night

    Ilikai 1236

    Ilikai 1236

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $219 to $280/night

    OTA House

    OTA House

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  51. $790 to $1,051/night

    Hale Ola Kai

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  52. $392 to $523/night

    Plantation Cottage

    Plantation Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  53. $1,434 to $4,626/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  54. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  55. $482 to $720/night

    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  56. $411 to $1,096/night

    Kona Makai 6301

    Kona Makai 6301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  57. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  58. $781 to $1,219/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  59. $563 to $781/night

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  60. $344 to $719/night

    Kapalua Golf Villa 15P78 Gold

    Kapalua Golf Villa 15P78 Gold

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  61. $594 to $1,063/night

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  62. $294 to $494/night

    Kapalua Ridge Villa 1721 Gold Ocean View

    Kapalua Ridge Villa 1721 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  63. $481 to $856/night

    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua Ridge Villa 1214 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  64. $294 to $563/night

    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua Golf Villa 25T4 Gold Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  65. $281 to $494/night

    Kapalua Golf Villa 11T4 Ocean View

    Kapalua Golf Villa 11T4 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  66. $288 to $494/night

    Kapalua Bay Villa 12G5 Ocean View

    Kapalua Bay Villa 12G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  67. $149 to $463/night

    Alii Villas #132

    Alii Villas #132

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $128 to $439/night

    THE SHORES OF MAUI #223

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $113 to $286/night

    Marine Surf Waikiki 2106

    Marine Surf Waikiki 2106

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $250 to $625/night

    Ilima Suite at The Ilikai (Unit 1226)

    Ilima Suite at The Ilikai (Unit 1226)

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $236 to $776/night

    Sea Village #4114

    Sea Village #4114

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $719 to $1,411/night

    Nai'a Hale

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  73. $145 to $465/night

    White Sands Village #120

    White Sands Village #120

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $219 to $649/night

    Kanaloa At Kona #3701

    Kanaloa At Kona #3701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $184 to $535/night

    Vista Waikoloa C305

    Vista Waikoloa C305

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $113 to $411/night

    Waikiki Gem at the Hawaiian King

    Waikiki Gem at the Hawaiian King

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $149 to $423/night

    Keauhou Resort #110

    Keauhou Resort #110

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $164 to $480/night

    Sea Village #3318

    Sea Village #3318

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $188 to $641/night

    WAILEA EKOLU #203

    WAILEA EKOLU #203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. $198 to $579/night

    Kanaloa At Kona #3001

    Kanaloa At Kona #3001

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $144 to $375/night

    White Sands Village #135

    White Sands Village #135

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $156 to $451/night

    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $250 to $734/night

    Royal Sea Cliff #418

    Royal Sea Cliff #418

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $119 to $350/night

    Casa De Emdeko #334

    Casa De Emdeko #334

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $250 to $734/night

    Kona Reef #D31

    Kona Reef #D31

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $1,000 to $2,903/night

    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $149 to $453/night

    White Sands Village #206

    White Sands Village #206

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $175 to $536/night

    Kona Bali Kai #206- 2 Bedroom

    Kona Bali Kai #206- 2 Bedroom

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $269 to $705/night

    Fairway Villas #K1 at the Waikoloa Beach Resort

    Fairway Villas #K1 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $226 to $790/night

    Na Hale O Keauhou #C6

    Na Hale O Keauhou #C6

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $119 to $338/night

    Keauhou Resort #111

    Keauhou Resort #111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. $625 to $1,649/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
  93. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. $300 to $480/night

    White Sands Village #201

    White Sands Village #201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $164 to $480/night

    Country Club Villas #208

    Country Club Villas #208

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $193 to $574/night

    Kona Nalu #302

    Kona Nalu #302

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $145 to $423/night

    Keauhou Punahele #B202

    Keauhou Punahele #B202

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $110 to $319/night

    Ilikai Marina 1783

    Ilikai Marina 1783

    1 Bedroom BathroomSleeps 3
    1 night minstay
    FREE CANCELLATION
  99. $157 to $415/night

    Ilikai Tower 633

    Ilikai Tower 633

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  100. $133 to $377/night

    Ilikai Tower 827

    Ilikai Tower 827

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION