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. $146 to $158/night

    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $327 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $371 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $144 to $186/night

    Palms Waikiki 815 Hotel Suites

    Palms Waikiki 815 Hotel Suites

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $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
  8. $142 to $569/night

    Royal Kahana 802

    Royal Kahana 802

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  9. $349 to $585/night

    A5-2 Beachfront Loft Suite

    A5-2 Beachfront Loft Suite

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  10. $332 to $388/night

    Sands Of Kahana 336

    Sands Of Kahana 336

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  11. $207 to $496/night

    Maui Eldorado Condo K217

    Maui Eldorado Condo K217

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  12. $371 to $458/night

    Kamaole Sands #05-406

    Kamaole Sands #05-406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $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
  14. $345 to $816/night

    Maui Eldorado Condo F204

    Maui Eldorado Condo F204

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $332 to $388/night

    Sands Of Kahana 373

    Sands Of Kahana 373

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  16. $1,797 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  17. $369 to $686/night

    Hale Mahina B401

    Hale Mahina B401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $169 to $408/night

    Maui Eldorado Condo C101

    Maui Eldorado Condo C101

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $234 to $476/night

    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $501 to $557/night

    Sands Of Kahana 356

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  21. $281 to $499/night

    2BR w/ Diamond Head Views & Lanai

    2BR w/ Diamond Head Views & Lanai

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  22. $260 to $311/night

    Kamaole Sands #09-102

    Kamaole Sands #09-102

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $350 to $417/night

    Kamaole Sands #08-105

    Kamaole Sands #08-105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $393 to $480/night

    Kamaole Sands #10-410

    Kamaole Sands #10-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $214 to $270/night

    Kahana Sunset B5B

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  27. $211 to $259/night

    Cliffs 1206

    Cliffs 1206

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $238 to $502/night

    Maui Eldorado Condo C102

    Maui Eldorado Condo C102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  29. $238 to $502/night

    Maui Eldorado Condo B105

    Maui Eldorado Condo B105

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. $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
  31. $207 to $501/night

    Maui Eldorado Condo K206

    Maui Eldorado Condo K206

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $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
  33. $169 to $230/night

    Kanaloa 202

    Kanaloa 202

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $230 to $466/night

    Royal Kahana 1012

    Royal Kahana 1012

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $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
  36. $191 to $419/night

    Royal Kahana 318

    Royal Kahana 318

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  37. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  38. $456 to $616/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  39. $310 to $535/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  40. $250 to $598/night

    Palm Leaf

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  41. $220 to $501/night

    Maui Eldorado Condo J120

    Maui Eldorado Condo J120

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $188 to $502/night

    Kaleialoha #207

    Kaleialoha #207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  43. $169 to $408/night

    Maui Eldorado Condo J216

    Maui Eldorado Condo J216

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. $158 to $350/night

    Kona Pacific B511

    Kona Pacific B511

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  45. $139 to $467/night

    Kona Plaza#220

    Kona Plaza#220

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $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
  47. $241 to $326/night

    Casa De Emdeko 111

    Casa De Emdeko 111

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $241 to $244/night

    Country Club Villas#115

    Country Club Villas#115

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  49. $250 to $533/night

    Maui Eldorado Condo G105

    Maui Eldorado Condo G105

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $145 to $242/night

    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $164 to $502/night

    Kaleialoha #214

    Kaleialoha #214

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $358 to $816/night

    Maui Eldorado Condo J100

    Maui Eldorado Condo J100

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $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
  54. $253 to $301/night

    Cliffs 8205

    Cliffs 8205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $235 to $301/night

    Cliffs 4205

    Cliffs 4205

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $241 to $301/night

    Cliffs 4206

    Cliffs 4206

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $207 to $620/night

    HOL 119

    HOL 119

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $186 to $375/night

    Kaleialoha 211

    Kaleialoha 211

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $344 to $374/night

    Wailea Ekolu 1604

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $249 to $499/night

    Kaanapali Royal G102

    Kaanapali Royal G102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $249 to $364/night

    Wailea Ekahi 49A

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. $160 to $286/night

    Napili Shores D230

    Napili Shores D230

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $438 to $563/night

    Grand Champions 124

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $211 to $324/night

    Napili Shores E243

    Napili Shores E243

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $117 to $243/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. $186 to $239/night

    Casa De Emdeko 204

    Casa De Emdeko 204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  67. $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
  68. $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
  69. $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
  70. $181 to $242/night

    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  71. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $493 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $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
  74. $122 to $394/night

    Royal Kahana #319

    Royal Kahana #319

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $354 to $1,133/night

    Royal Kahana #911

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. $336 to $706/night

    Kaanapali Shores #825

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  77. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  78. $276 to $332/night

    Kahana Sunset C5

    Kahana Sunset C5

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  79. $330 to $612/night

    Hanalei Bay Resort 8133/4

    Hanalei Bay Resort 8133/4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $192 to $234/night

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $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
  82. $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
  83. $169 to $300/night

    Eldorado E104

    Eldorado E104

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  86. $233 to $344/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $198 to $298/night

    Maui Vista 2211

    Maui Vista 2211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $234 to $311/night

    Pacific Shores B406

    Pacific Shores B406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $194 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. $271 to $368/night

    Kaanapali Shores 546

    Kaanapali Shores 546

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $503 to $649/night

    Maalaea Banyans 408

    Maalaea Banyans 408

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $254 to $344/night

    Mahina Surf 220

    Mahina Surf 220

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  93. $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
  94. $344 to $719/night

    Kapalua Golf Villa 15P78 Gold

    Kapalua Golf Villa 15P78 Gold

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  95. $196 to $303/night

    Papakea E306

    Papakea E306

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  96. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  97. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  98. $281 to $494/night

    Kapalua Golf Villa 11T4 Ocean View

    Kapalua Golf Villa 11T4 Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  99. $275 to $466/night

    Eldorado K203

    Eldorado K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $326 to $509/night

    International Colony Club 20

    International Colony Club 20

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION