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. $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
  2. $360 to $557/night

    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  3. $168 to $197/night

    Palms Waikiki 720

    Palms Waikiki 720

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $262 to $547/night

    Waipouli Beach Resort D-309

    Waipouli Beach Resort D-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  5. $327 to $636/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  6. $688 to $1,623/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  7. $204 to $238/night

    Mauna Kai 5A

    Mauna Kai 5A

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  8. $227 to $293/night

    Alii Kai 3103

    Alii Kai 3103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  9. $156 to $274/night

    Hale Ono Loa 401

    Hale Ono Loa 401

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $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
  11. $245 to $363/night

    Poipu Kapili 46

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  12. $227 to $285/night

    Sealodge J1

    Sealodge J1

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  13. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  14. $173 to $279/night

    Kahana Villa F410

    Kahana Villa F410

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $334 to $408/night

    Kauai Tree House

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  16. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  17. $291 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  18. $240/night

    Keauhou Elima

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool
  19. $227 to $275/night

    Sealodge J9

    Sealodge J9

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  20. $257 to $346/night

    Nihilani 22C

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool
  21. $260 to $346/night

    Pali Ke Kua #204

    Pali Ke Kua #204

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  22. $1,008 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  23. $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
  24. $261 to $363/night

    Plantations at Princeville #1212

    Plantations at Princeville #1212

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  25. $525 to $1,205/night

    Wai'ula'ula A202

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  28. $311 to $564/night

    Waipouli Beach Resort A-303

    Waipouli Beach Resort A-303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  29. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. $156 to $229/night

    Valley Isle #1106

    Valley Isle #1106

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  31. $88 to $286/night

    Kona Bali Kai Studio w/ Pool & Spa

    Kona Bali Kai Studio w/ Pool & Spa

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $340 to $508/night

    Waipouli Beach Resort E-205

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  33. $247 to $282/night

    Pali Ke Kua #118

    Pali Ke Kua #118

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  34. $201 to $274/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  35. $112 to $156/night

    Sandpiper 121B

    Sandpiper 121B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $363 to $525/night

    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  37. $184 to $431/night

    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $231 to $275/night

    Sealodge D1

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  39. $493 to $1,174/night

    Wai'ula'ula D201

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  41. $216 to $407/night

    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $260 to $437/night

    Puu Poa #305

    Puu Poa #305

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  43. $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
  44. $250 to $625/night

    Ilima Suite at The Ilikai (Unit 1226)

    Ilima Suite at The Ilikai (Unit 1226)

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $144 to $260/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. $145 to $258/night

    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  47. $216 to $407/night

    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $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
  49. $238 to $598/night

    Palm Leaf

    Palm Leaf

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  50. $145 to $569/night

    Lahaina Shores 210

    Lahaina Shores 210

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  51. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. $280 to $349/night

    Diamond Head Beach Hotel 602

    Diamond Head Beach Hotel 602

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  53. $394 to $473/night

    Diamond Head Beach Hotel PH01

    Diamond Head Beach Hotel PH01

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  54. $174 to $242/night

    Palms Waikiki 506

    Palms Waikiki 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $321 to $444/night

    Diamond Head Beach Hotel 601

    Diamond Head Beach Hotel 601

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  56. $236 to $636/night

    Kuleana 313

    Kuleana 313

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  57. $310 to $605/night

    Melemele Pua

    Melemele Pua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  58. $286 to $586/night

    Surfs Up

    Surfs Up

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  59. $238 to $478/night

    Tropical Breeze

    Tropical Breeze

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  60. $383 to $581/night

    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $156 to $274/night

    Hale Ono Loa 205

    Hale Ono Loa 205

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  62. $234 to $464/night

    Waikoloa Beach Villas E33

    Waikoloa Beach Villas E33

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $194 to $238/night

    Puamana 21D

    Puamana 21D

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  64. $270 to $340/night

    Hale Kohea

    Hale Kohea

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  65. $227 to $275/night

    Sealodge C7

    Sealodge C7

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  66. $412 to $741/night

    Waikoloa Beach Villas I1

    Waikoloa Beach Villas I1

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $204 to $238/night

    Puamana 9C

    Puamana 9C

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. $215 to $269/night

    Sealodge E8

    Sealodge E8

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  69. $353 to $610/night

    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. $240 to $308/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  71. $656 to $875/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  72. $234 to $465/night

    Hale Mahina A-403

    Hale Mahina A-403

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  73. $202 to $315/night

    Alii Kai 5301

    Alii Kai 5301

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. $164 to $231/night

    Sea Village 1-203

    Sea Village 1-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $209 to $464/night

    Shores at Waikoloa #234 at Bo Tree Tower

    Shores at Waikoloa #234 at Bo Tree Tower

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $304 to $467/night

    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  77. $416 to $664/night

    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  78. $173 to $263/night

    Valley Isle #1104

    Valley Isle #1104

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  79. $183 to $214/night

    Villas on the Prince 34

    Villas on the Prince 34

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $516 to $722/night

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  81. $218 to $446/night

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. $180 to $319/night

    New Listing! Ocean-View Apartment w/ Pool & Spa

    New Listing! Ocean-View Apartment w/ Pool & Spa

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $145 to $276/night

    Ocean-View Golf Getaway: Pool & Tennis- Near Beach

    Ocean-View Golf Getaway: Pool & Tennis- Near Beach

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $370 to $901/night

    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  85. $234 to $464/night

    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $215 to $257/night

    Sealodge G4

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  87. $177 to $334/night

    Plantations at Princeville #1122

    Plantations at Princeville #1122

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  88. $228 to $347/night

    Plantations at Princeville #521

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  89. $330 to $689/night

    Big Island Paradise

    Big Island Paradise

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  90. $155 to $372/night

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  91. $311 to $426/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  92. $234 to $464/night

    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $162 to $401/night

    Kolepa Aloha

    Kolepa Aloha

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  94. $192 to $260/night

    Alii Kai II 11B

    Alii Kai II 11B

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $757 to $759/night

    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. $361 to $479/night

    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    4 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  97. $172 to $282/night

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $234 to $464/night

    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  99. $358 to $514/night

    Regency at Poipu Kai #924

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  100. $189 to $384/night

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION