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. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $134 to $213/night

    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    2 BedroomsBathroomsSleeps 4
    12 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $250 to $741/night

    Pohailani 231

    Pohailani 231

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $201 to $224/night

    Tradewinds Plaza 305

    Tradewinds Plaza 305

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  5. $167 to $248/night

    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $108/night

    Kuhio Village 410 Condominium

    Kuhio Village 410 Condominium

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  7. $177 to $225/night

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $237/night

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults only

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults ...

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $140 to $413/night

    HOL #216

    HOL #216

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $226 to $344/night

    Papakea A309

    Papakea A309

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  11. $505 to $711/night

    Papakea A404

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  12. $152 to $443/night

    HOL 311

    HOL 311

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $249 to $312/night

    Malolo Cottage

    Malolo Cottage

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  14. $228 to $409/night

    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $258 to $340/night

    252

    252

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  16. $300 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $220 to $238/night

    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $219 to $438/night

    Maui Kai 206

    Maui Kai 206

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $179 to $258/night

    Waikiki Banyan Tower 1 Suite 2214- KP

    Waikiki Banyan Tower 1 Suite 2214- KP

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $199 to $236/night

    WB910 Waikiki Heaven on Earth Ocean View

    WB910 Waikiki Heaven on Earth Ocean View

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $188 to $258/night

    237

    237

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $226 to $776/night

    Kanaloa 2201

    Kanaloa 2201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $195 to $593/night

    Surf & Racquet Club #3-201

    Surf & Racquet Club #3-201

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. $186 to $509/night

    Surf & Racquet Club #6-303

    Surf & Racquet Club #6-303

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  25. $576 to $746/night

    Laulea Hale

    Laulea Hale

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  26. $424 to $1,125/night

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $4,194 to $7,190/night

    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  28. $188 to $321/night

    Maui Kai 108

    Maui Kai 108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $426 to $531/night

    Wailea Ekolu 1606

    Wailea Ekolu 1606

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $186 to $236/night

    Napili Shores D127

    Napili Shores D127

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $344 to $606/night

    Maui Kai 601

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $176 to $249/night

    Royal Kahana 618

    Royal Kahana 618

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $246 to $361/night

    Kaleialoha 309

    Kaleialoha 309

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  35. $238 to $379/night

    Kihei Akahi Resort- Unit B204

    Kihei Akahi Resort- Unit B204

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  36. $180 to $345/night

    Kaanapali Shores 936

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $406 to $585/night

    Hale Ono Loa 409

    Hale Ono Loa 409

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $299 to $449/night

    Mahana 713

    Mahana 713

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $208 to $250/night

    Hale Kamaole 109

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $274 to $455/night

    Kaanapali Royal B303

    Kaanapali Royal B303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  42. $276 to $370/night

    Honua Kai 322

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  44. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  45. $176 to $502/night

    Kaleialoha #114

    Kaleialoha #114

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $402 to $981/night

    Pacific Edge Kona

    Pacific Edge Kona

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  47. $423 to $910/night

    Kona Nalu 304

    Kona Nalu 304

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  48. $314 to $764/night

    Poipu Crater

    Poipu Crater

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  49. $482 to $1,234/night

    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  50. $631 to $1,534/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  51. $1,266 to $3,944/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  52. $1,169 to $3,369/night

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  53. $324 to $588/night

    Sands of Kahana 316

    Sands of Kahana 316

    2 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $845 to $2,366/night

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  55. $357 to $871/night

    Mauna Kai 2

    Mauna Kai 2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  56. $152 to $502/night

    Kaleialoha #413

    Kaleialoha #413

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  57. $274 to $409/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $202 to $238/night

    Kamahana 24

    Kamahana 24

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  59. $205 to $358/night

    Aina Nalu A 201

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $293 to $356/night

    Papakea K306

    Papakea K306

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $305 to $448/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  63. $259 to $394/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $258 to $340/night

    330

    330

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  65. $206 to $348/night

    Plantations at Princeville #111

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  66. $250 to $346/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  68. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  69. $258 to $393/night

    309

    309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. $236 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  71. $118 to $261/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. $249 to $368/night

    Papakea A108

    Papakea A108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  73. $188 to $502/night

    Kaleialoha #113

    Kaleialoha #113

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $353 to $429/night

    Papakea L108

    Papakea L108

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $339 to $861/night

    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  77. $582 to $1,325/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  78. $397 to $1,209/night

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  79. $188 to $258/night

    113

    113

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. $188 to $297/night

    236

    236

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  81. $427 to $775/night

    Molokama

    Molokama

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  82. $289 to $435/night

    Napili Point A8

    Napili Point A8

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $423 to $1,102/night

    Kanaloa at Kona 3304

    Kanaloa at Kona 3304

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  84. $274 to $686/night

    Kaanapali Royal N102

    Kaanapali Royal N102

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $188 to $258/night

    240

    240

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $249 to $368/night

    Papakea A307

    Papakea A307

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  87. $199 to $239/night

    Aina Nalu K 205

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $234 to $476/night

    Waikoloa Beach Villas H32

    Waikoloa Beach Villas H32

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  89. $365 to $443/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  90. $311 to $938/night

    Kaanapali Shores 403

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $235 to $317/night

    342

    342

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. $258 to $340/night

    344

    344

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  93. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $516 to $620/night

    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $161 to $274/night

    Kaanapali Shores 628

    Kaanapali Shores 628

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $456 to $660/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  98. $311 to $736/night

    Whaler 859

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $1,318 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  100. $269 to $409/night

    276

    276

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION