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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. $294 to $494/night

    Kapalua Ridge Villa 114 Gold Ocean View

    Kapalua Ridge Villa 114 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  2. $368 to $1,070/night

    Mauna Lani Golf Villas #N4

    Mauna Lani Golf Villas #N4

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  3. $625 to $1,648/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
  4. $219 to $431/night

    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  5. $169 to $300/night

    Eldorado E104

    Eldorado E104

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $304 to $456/night

    Eldorado G205

    Eldorado G205

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  9. $233 to $344/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $198 to $298/night

    Maui Vista 2211

    Maui Vista 2211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $224 to $458/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $299 to $426/night

    Eldorado H107

    Eldorado H107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $261 to $386/night

    Kahana Sunset C1

    Kahana Sunset C1

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $374 to $571/night

    Pacific Shores B102

    Pacific Shores B102

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $234 to $311/night

    Pacific Shores B406

    Pacific Shores B406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $194 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $313 to $469/night

    Wailea Ekahi 50C

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $271 to $368/night

    Kaanapali Shores 546

    Kaanapali Shores 546

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $503 to $649/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $254 to $344/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $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
  22. $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
  23. $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
  24. $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
  25. $294 to $494/night

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  26. $344 to $719/night

    Kapalua Golf Villa 15P78 Gold

    Kapalua Golf Villa 15P78 Gold

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  27. $196 to $303/night

    Papakea E306

    Papakea E306

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  28. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  29. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  31. $281 to $494/night

    Kapalua Golf Villa 11T4 Ocean View

    Kapalua Golf Villa 11T4 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  32. $469 to $680/night

    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $254 to $456/night

    Mahana 602

    Mahana 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $275 to $466/night

    Eldorado K203

    Eldorado K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $326 to $509/night

    International Colony Club 20

    International Colony Club 20

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $313 to $438/night

    Maui Banyan Q204

    Maui Banyan Q204

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $338 to $561/night

    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $200 to $301/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $215 to $331/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $556 to $1,063/night

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  41. $311 to $365/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $235 to $324/night

    PuaMana 175-2

    PuaMana 175-2

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $230 to $461/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $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
  45. $563 to $781/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  46. $282 to $538/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  47. $855 to $1,319/night

    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  48. $706 to $1,038/night

    MAKENA SURF RESORT, #C-103

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  49. $256 to $461/night

    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  50. $191 to $355/night

    Royal Kahana 702

    Royal Kahana 702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  51. $199 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
  52. $282 to $484/night

    Honua Kai 506

    Honua Kai 506

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $304 to $436/night

    Honua Kai 1024

    Honua Kai 1024

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $470 to $953/night

    WAILEA ELUA, #0802

    WAILEA ELUA, #0802

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  55. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  56. $357 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
  57. $243 to $433/night

    Aina Nalu B204

    Aina Nalu B204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $397 to $1,209/night

    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  59. $288 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $242 to $292/night

    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  61. $369 to $688/night

    Kapalua Golf Villa 23V3 Ocean View

    Kapalua Golf Villa 23V3 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  62. $411 to $947/night

    Kona Makai 6301

    Kona Makai 6301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  63. $267 to $568/night

    Kona Makai 6305

    Kona Makai 6305

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
  64. $181 to $239/night

    Hale Pineapple

    Hale Pineapple

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  65. $481 to $899/night

    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  66. $631 to $1,335/night

    Koa Kai Hale

    Koa Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  67. $296 to $447/night

    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. $387 to $1,038/night

    Pili Mai 11I

    Pili Mai 11I

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  69. $344 to $624/night

    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. $195 to $299/night

    Napili Shores E240

    Napili Shores E240

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $1,328 to $3,627/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
  72. $363 to $869/night

    Pili Mai 3G

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  73. $766 to $2,122/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  74. $280 to $595/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  75. $1,131 to $3,225/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
  76. $500 to $1,095/night

    Waikoloa Beach Villas A4

    Waikoloa Beach Villas A4

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  77. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  79. $508 to $1,789/night

    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  80. $350 to $417/night

    Kamaole Sands #08-410

    Kamaole Sands #08-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $362 to $977/night

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  82. $240 to $343/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  84. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  85. $215 to $331/night

    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. $209 to $354/night

    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $313 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $379 to $483/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $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
  90. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  91. $306 to $358/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  93. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $281 to $463/night

    Kapalua Golf Villa 14T

    Kapalua Golf Villa 14T

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  95. $406 to $720/night

    Mauna Lani Golf Villas C1

    Mauna Lani Golf Villas C1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  96. $223 to $306/night

    Hale Mala Hina-245

    Hale Mala Hina-245

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  97. $627 to $1,065/night

    Wailea Elua, #0908

    Wailea Elua, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  98. $232 to $406/night

    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $241 to $271/night

    Plantation 1111

    Plantation 1111

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $706 to $1,038/night

    MAKENA SURF RESORT, #C-102

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub