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. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  2. $327 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $371 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $191 to $636/night

    Maui Ka'anapali Villas Studio Premier Condo A417

    Maui Ka'anapali Villas Studio Premier Condo A417

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  5. $142 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  6. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  7. $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
  8. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $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
  10. $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
  11. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  12. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $223 to $306/night

    Hale Mala Hina-245

    Hale Mala Hina-245

    2 Bedrooms BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $288 to $348/night

    Kahana Sunset E 11

    Kahana Sunset E 11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  16. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  17. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $443 to $861/night

    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  19. $320 to $703/night

    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    3 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  20. $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
  21. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $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
  23. $349 to $585/night

    A5-2 Beachfront Loft Suite

    A5-2 Beachfront Loft Suite

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  24. $306/night

    Kulakane 304

    Kulakane 304

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  25. $428 to $484/night

    Kahana Sunset F1

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  26. $276 to $332/night

    Kahana Sunset E6

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  27. $309 to $366/night

    Kahana Sunset B8

    Kahana Sunset B8

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  28. $332 to $388/night

    Sands Of Kahana 344

    Sands Of Kahana 344

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  29. $428 to $484/night

    Kahana Sunset F12

    Kahana Sunset F12

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  30. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  31. $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
  32. $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
  33. $282 to $484/night

    Honua Kai 506

    Honua Kai 506

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  35. $311 to $365/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $371 to $458/night

    Kamaole Sands #05-406

    Kamaole Sands #05-406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $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
  38. $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
  39. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  40. $306 to $358/night

    Honua Kai Konea 215

    Honua Kai Konea 215

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  43. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  44. $371 to $458/night

    Kamaole Sands #06-310

    Kamaole Sands #06-310

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $393 to $480/night

    Kamaole Sands #08-411

    Kamaole Sands #08-411

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $260 to $311/night

    Kamaole Sands #09-102

    Kamaole Sands #09-102

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $290 to $332/night

    Kamaole Sands #07-306

    Kamaole Sands #07-306

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $350 to $417/night

    Kamaole Sands #08-105

    Kamaole Sands #08-105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $371 to $458/night

    Kamaole Sands #06-405

    Kamaole Sands #06-405

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $350 to $417/night

    Kamaole Sands #08-410

    Kamaole Sands #08-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  51. $393 to $480/night

    Kamaole Sands #10-407

    Kamaole Sands #10-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $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
  53. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  54. $393 to $480/night

    Kamaole Sands #10-410

    Kamaole Sands #10-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  57. $282 to $538/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  58. $339 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
  59. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  60. $455 to $1,035/night

    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    3 Bedrooms2.5 BathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  61. $169 to $230/night

    Kanaloa 202

    Kanaloa 202

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $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
  63. $256 to $461/night

    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  64. $176 to $502/night

    Kaleialoha #115

    Kaleialoha #115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $224 to $357/night

    Plantations at Princeville #1212

    Plantations at Princeville #1212

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  66. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  67. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  68. $456 to $616/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  69. $310 to $535/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  70. $158 to $350/night

    Kona Pacific B511

    Kona Pacific B511

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  71. $228 to $350/night

    Keauhou Kona Surf & Racquet Club#37

    Keauhou Kona Surf & Racquet Club#37

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  72. $241 to $326/night

    Casa De Emdeko 111

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $241 to $244/night

    Country Club Villas#115

    Country Club Villas#115

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $432 to $861/night

    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  75. $363 to $985/night

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $246 to $617/night

    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $186 to $375/night

    Kaleialoha 211

    Kaleialoha 211

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. $344 to $374/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  79. $249 to $499/night

    Kaanapali Royal G102

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $249 to $364/night

    Wailea Ekahi 49A

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  81. $438 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $459 to $625/night

    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $344 to $435/night

    Lauloa 105

    Lauloa 105

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $117 to $243/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $186 to $239/night

    Casa De Emdeko 204

    Casa De Emdeko 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $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
  87. $235 to $324/night

    PuaMana 175-2

    PuaMana 175-2

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $281 to $790/night

    Na Hale O Keauhou #C6

    Na Hale O Keauhou #C6

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $149 to $450/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
  90. $269 to $704/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
  91. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $531 to $969/night

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  94. $232 to $406/night

    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  95. $209 to $354/night

    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $215 to $331/night

    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  97. $122 to $394/night

    Royal Kahana #319

    Royal Kahana #319

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $191 to $331/night

    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $354 to $1,133/night

    Royal Kahana #911

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $284 to $706/night

    Kaanapali Shores #916

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION