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. $161 to $473/night

    Ilikai Marina 1392

    Ilikai Marina 1392

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  2. $154 to $445/night

    Ilikai Tower 814

    Ilikai Tower 814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  3. $128 to $345/night

    Ilikai Tower 611

    Ilikai Tower 611

    1 Bedroom BathroomSleeps 3
    1 night minstay
    Pool
    FREE CANCELLATION
  4. $899 to $2,681/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  5. $280 to $706/night

    Sea Village 4107

    Sea Village 4107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  6. $227 to $508/night

    Kona Mansions E-334

    Kona Mansions E-334

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  7. $250 to $575/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
  8. $542 to $1,330/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  9. $393 to $972/night

    Maile Hale

    Maile Hale

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  10. $690 to $2,037/night

    Ohana Kamalani

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  11. $211 to $249/night

    WB1909 Waikiki Steps to the Beach Wifi Ocean View

    WB1909 Waikiki Steps to the Beach Wifi Ocean View

    1 Bedroom BathroomSleeps 5
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $224 to $286/night

    WS2105 Your Waikiki Paradise Awaits New Gym, AC

    WS2105 Your Waikiki Paradise Awaits New Gym, AC

    Studio BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  13. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  14. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  15. $240/night

    Keauhou Elima

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool
  16. $335 to $390/night

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 6

    2 BedroomsBathroomsSleeps 6
    3 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. $220 to $597/night

    Valley Isle #1103

    Valley Isle #1103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $325 to $603/night

    Papakea #A109

    Papakea #A109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $220 to $522/night

    Hololani #B-802

    Hololani #B-802

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $354 to $969/night

    Royal Kahana #911

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. $313 to $606/night

    Mahana Resort #1017

    Mahana Resort #1017

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $310 to $580/night

    Kaanapali Royal #N302

    Kaanapali Royal #N302

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. $128 to $255/night

    Paki Maui #420

    Paki Maui #420

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $264 to $271/night

    New Listing! Hawaiian Experience- Walk to Two Step

    New Listing! Hawaiian Experience- Walk to Two Step

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  26. $278 to $640/night

    Lokelani #C205

    Lokelani #C205

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $145 to $319/night

    Papakea #B207

    Papakea #B207

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $278 to $600/night

    Kaanapali Royal #A303

    Kaanapali Royal #A303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $278 to $638/night

    Kaanapali Royal #H302

    Kaanapali Royal #H302

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $296 to $447/night

    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $261 to $539/night

    Pikake #A6

    Pikake #A6

    2 Bedrooms1.5  BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  32. $336 to $606/night

    Mahana Resort #304

    Mahana Resort #304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $232 to $447/night

    Lahaina Shores #425

    Lahaina Shores #425

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $180 to $441/night

    Papakea #D304

    Papakea #D304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $290 to $806/night

    Lahaina Roads #201

    Lahaina Roads #201

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $324 to $669/night

    Mahana Resort #706

    Mahana Resort #706

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $162 to $371/night

    Papakea #D309

    Papakea #D309

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $122 to $331/night

    Royal Kahana #319

    Royal Kahana #319

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $284 to $586/night

    Kaanapali Royal #C101

    Kaanapali Royal #C101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $302 to $669/night

    Lahaina Shores #501

    Lahaina Shores #501

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $232 to $551/night

    Valley Isle #1209

    Valley Isle #1209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  42. $232 to $568/night

    Valley Isle #1203

    Valley Isle #1203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $383 to $835/night

    Papakea #D402

    Papakea #D402

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $261 to $619/night

    Papakea #E401

    Papakea #E401

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $232 to $414/night

    Lahaina Roads #206

    Lahaina Roads #206

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $325 to $638/night

    Mahana Resort #1106

    Mahana Resort #1106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  47. $342 to $669/night

    Mahana Resort #616

    Mahana Resort #616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. $284 to $644/night

    Kaanapali Shores #916

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  49. $162 to $332/night

    Paki Maui #109

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $215 to $331/night

    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $209 to $354/night

    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $273 to $600/night

    Hale Mahina #B404

    Hale Mahina #B404

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $209 to $433/night

    Aina Nalu #A109

    Aina Nalu #A109

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. $180 to $478/night

    Hale Mahina #B103

    Hale Mahina #B103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $157 to $423/night

    Valley Isle #1206

    Valley Isle #1206

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. $273 to $447/night

    Lahaina Shores #531

    Lahaina Shores #531

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $290 to $653/night

    Papakea #L407

    Papakea #L407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $319 to $574/night

    Mahana Resort #804

    Mahana Resort #804

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $290 to $619/night

    Papakea #G408

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $191 to $408/night

    Lokelani #C104

    Lokelani #C104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  61. $203 to $383/night

    Papakea #C108

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. $191 to $331/night

    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  63. $296 to $580/night

    Papakea #H103

    Papakea #H103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $290 to $551/night

    Papakea #G106

    Papakea #G106

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $406 to $566/night

    Paki Maui #421

    Paki Maui #421

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $232 to $406/night

    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $336 to $706/night

    Kaanapali Shores #825

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $139 to $307/night

    Valley Isle #107

    Valley Isle #107

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $412 to $940/night

    Papakea #C403

    Papakea #C403

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $191 to $447/night

    Hale Mahina #B303

    Hale Mahina #B303

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $220 to $532/night

    Hololani #B-403

    Hololani #B-403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  72. $261 to $488/night

    Puamana 52-3

    Puamana 52-3

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  73. $608 to $846/night

    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $292 to $350/night

    Keauhou Kona Surf & Racquet Club #3-101 "Hale Malama Pono"

    Keauhou Kona Surf & Racquet Club #3-101 "Hale M...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $164 to $971/night

    Kona Isle #C38

    Kona Isle #C38

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $256 to $461/night

    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  77. $526 to $860/night

    Papakea K-402

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $217 to $423/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $513 to $937/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $204 to $333/night

    Pohailani Maui 115

    Pohailani Maui 115

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  81. $191 to $359/night

    Royal Kahana 318

    Royal Kahana 318

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  82. $204 to $333/night

    Pohailani Maui 152

    Pohailani Maui 152

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  83. $191 to $333/night

    Royal Kahana 702

    Royal Kahana 702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  84. $193 to $333/night

    Kaanapali Shores Studio 742

    Kaanapali Shores Studio 742

    Studio BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  85. $269 to $461/night

    Kapalua Golf Villa 14T

    Kapalua Golf Villa 14T

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  86. $780 to $1,618/night

    Hale Emmalani

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  87. $1,434 to $3,267/night

    Blue Oasis*

    Blue Oasis*

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  88. $1,160 to $4,404/night

    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  89. $256 to $544/night

    Keauhou Resort 104

    Keauhou Resort 104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  90. $252 to $675/night

    Waikoloa Villas F-100

    Waikoloa Villas F-100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  91. $780 to $1,395/night

    Hale Poola

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  92. $405 to $720/night

    Nui Lani

    Nui Lani

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  93. $799 to $2,616/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  94. $1,102 to $3,791/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  95. $386 to $993/night

    Onomea Cliffside Cottage

    Onomea Cliffside Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
  96. $280 to $683/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  97. $481 to $899/night

    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  98. $957 to $1,553/night

    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  99. $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
  100. $276 to $586/night

    Hilo Lagoon Center #526

    Hilo Lagoon Center #526

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool