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. $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
  2. $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
  3. $188 to $469/night

    Wailea Ekahi 50C

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $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
  5. $281 to $438/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $280 to $596/night

    Waikoloa Colony Villas 403

    Waikoloa Colony Villas 403

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  7. $369 to $625/night

    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $571 to $1,789/night

    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  10. $235 to $324/night

    PuaMana 175-2

    PuaMana 175-2

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $256 to $469/night

    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  12. $177 to $303/night

    Papakea E306

    Papakea E306

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  13. $193 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $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
  15. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  16. $393 to $480/night

    Kamaole Sands #10-407

    Kamaole Sands #10-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $215 to $331/night

    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $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
  19. $350 to $417/night

    Kamaole Sands #08-410

    Kamaole Sands #08-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $188 to $438/night

    Lauloa 105

    Lauloa 105

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  21. $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
  22. $397 to $717/night

    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  23. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  24. $209 to $354/night

    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $354 to $1,133/night

    Royal Kahana #911

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $232 to $406/night

    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  27. $193 to $306/night

    Hale Mala Hina-245

    Hale Mala Hina-245

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $296 to $447/night

    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $1,045 to $1,371/night

    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  31. $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
  32. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  33. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  34. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $249 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $288 to $494/night

    Kapalua Bay Villa 12G5 Ocean View

    Kapalua Bay Villa 12G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  37. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  38. $186 to $375/night

    Kaleialoha 211

    Kaleialoha 211

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  40. $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
  41. $320 to $703/night

    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    3 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  42. $283 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $188 to $486/night

    Pacific Shores B102

    Pacific Shores B102

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $165 to $360/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $224 to $454/night

    Honua Kai 1024

    Honua Kai 1024

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $344 to $675/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $273 to $581/night

    Napili Point B5

    Napili Point B5

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. $281 to $438/night

    Maui Banyan Q204

    Maui Banyan Q204

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $184 to $389/night

    Wailea Ekahi 49A

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $213 to $493/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $176 to $502/night

    Kaleialoha #115

    Kaleialoha #115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  53. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  56. $281 to $311/night

    Kulakane 304

    Kulakane 304

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  57. $219 to $431/night

    Kapalua Ridge Villa #1521

    Kapalua Ridge Villa #1521

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $186 to $330/night

    Maui Sunset B402

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $349 to $585/night

    A5-2 Beachfront Loft Suite

    A5-2 Beachfront Loft Suite

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  60. $161 to $298/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $224 to $499/night

    Kaanapali Royal G102

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $221 to $499/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  64. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  65. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  67. $371 to $458/night

    Kamaole Sands #06-405

    Kamaole Sands #06-405

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. $191 to $331/night

    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  69. $159 to $318/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $290 to $332/night

    Kamaole Sands #07-306

    Kamaole Sands #07-306

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $186 to $333/night

    Kaleialoha 203

    Kaleialoha 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  73. $276 to $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  74. $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
  75. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  76. $261 to $363/night

    Plantations at Princeville #1212

    Plantations at Princeville #1212

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  77. $433 to $606/night

    Whaler at Kaanapali Beach 514

    Whaler at Kaanapali Beach 514

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $217 to $447/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $158 to $350/night

    Kona Pacific B511

    Kona Pacific B511

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $218 to $429/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $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
  84. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  85. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  86. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  87. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  88. $174 to $313/night

    Maui Vista 2211

    Maui Vista 2211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  89. $347 to $466/night

    Hale Kohola

    Hale Kohola

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  90. $193 to $255/night

    Holoholo ku Waimea

    Holoholo ku Waimea

    3 BedroomsBathroomsSleeps 6
    14 nights minstay
    FREE CANCELLATION
  91. $236/night

    Waikiki Beach Walk 2 Bedroom

    Waikiki Beach Walk 2 Bedroom

    Multiple Units Available
    3 nights minstay
    Pool Hot Tub
  92. $174 to $299/night

    Eldorado J109

    Eldorado J109

    Studio BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $281 to $332/night

    Kamaole Sands #09-309

    Kamaole Sands #09-309

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $260 to $311/night

    Kamaole Sands #04-312

    Kamaole Sands #04-312

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $304 to $467/night

    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  96. $259 to $428/night

    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  97. $259 to $428/night

    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  98. $416 to $664/night

    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  99. $506 to $563/night

    Sands Of Kahana 215

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  100. $416 to $664/night

    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION