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. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $473 to $842/night

  2. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  3. CONDOMINIUM
    Waiohuli Beach Hale #D-220

    Waiohuli Beach Hale #D-220

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  4. CONDOMINIUM
    Waiohuli Beach Hale #D-120

    Waiohuli Beach Hale #D-120

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  5. CONDOMINIUM
    Waiohuli Beach Hale #D-114

    Waiohuli Beach Hale #D-114

    Kihei, HI

    Pool
    FREE CANCELLATION

    $167 to $398/night

  6. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Pool
    FREE CANCELLATION

    $208 to $347/night

  7. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Pool
    FREE CANCELLATION

    $255 to $610/night

  8. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Pool
    FREE CANCELLATION

    $401 to $618/night

  9. CONDOMINIUM
    Wailea Ekolu #805

    Wailea Ekolu #805

    Wailea, HI

    Pool
    FREE CANCELLATION

    $249 to $481/night

  10. CONDOMINIUM
    Wailea Ekolu #804

    Wailea Ekolu #804

    Wailea, HI

    Pool
    FREE CANCELLATION

    $261 to $405/night

  11. CONDOMINIUM
    Wailea Ekahi 36C

    Wailea Ekahi 36C

    Wailea, HI

    Pool
    FREE CANCELLATION

    $228 to $555/night

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

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

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $192 to $295/night

  13. CONDOMINIUM
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $333 to $703/night

  14. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  15. VILLA
    Waikoloa Beach Villas I1

    Waikoloa Beach Villas I1

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $741/night

  16. CONDOMINIUM
    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $476/night

  17. CONDOMINIUM
    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  18. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  19. CONDOMINIUM
    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $464/night

  20. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  21. CONDOMINIUM
    Waikiki Grand Condominium 922 *Legal Vacation Rental

    Waikiki Grand Condominium 922 *Legal Vacation Rental

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $111 to $269/night

  22. CONDOMINIUM
    Waikiki Grand Condominium 705 *Legal Vacation Rental

    Waikiki Grand Condominium 705 *Legal Vacation Rental

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $96 to $224/night

  23. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,174/night

  24. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  25. CONDOMINIUM
    Vista Waikoloa G-104

    Vista Waikoloa G-104

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  26. CONDOMINIUM
    Vista Waikoloa E-105

    Vista Waikoloa E-105

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  27. CONDOMINIUM
    Vista Waikoloa D-102

    Vista Waikoloa D-102

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  28. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $183/night

  29. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $164 to $183/night

  30. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  31. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $901/night

  32. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $760/night

  33. CONDOMINIUM
    Valley Isle 902

    Valley Isle 902

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $176 to $398/night

  34. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $312/night

  35. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $330/night

  36. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

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

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

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $174 to $444/night

  38. CONDOMINIUM
    Tropical Breeze

    Tropical Breeze

    Waikoloa, HI

    Pool Hot Tub

    $238 to $478/night

  39. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  40. CONDOMINIUM
    The Plantation #1

    The Plantation #1

    Lahaina, HI

    FREE CANCELLATION

    $329 to $549/night

  41. CONDOMINIUM
    The Montage Kapalua Bay- Heliconia 2302- Ocean View Paradise!

    The Montage Kapalua Bay- Heliconia 2302- Ocean View Para...

    Kapalua, HI

    Pool Hot Tub

    $1,297 to $3,687/night

  42. CONDOMINIUM
    The Mauna Lani Golf Villas K5

    The Mauna Lani Golf Villas K5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  43. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  44. CONDOMINIUM
    Surfs Up

    Surfs Up

    Waikoloa, HI

    Pool Hot Tub

    $286 to $586/night

  45. CONDOMINIUM
    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach

    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach...

    Kihei, HI

    Pool
    FREE CANCELLATION

    $112 to $353/night

  46. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $544/night

  47. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $579/night

  48. HOUSE
    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    Serene 3BR w/ Lanai & Private Yard, Walk to Beach

    Honolulu, HI

    FREE CANCELLATION

    $325 to $792/night

  49. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $257/night

  50. CONDOMINIUM
    Sealodge J1

    Sealodge J1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  51. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  52. CONDOMINIUM
    Sealodge G4

    Sealodge G4

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  53. CONDOMINIUM
    Sealodge G3

    Sealodge G3

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  54. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  55. CONDOMINIUM
    Sealodge E8

    Sealodge E8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  56. CONDOMINIUM
    Sealodge E10

    Sealodge E10

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $275/night

  57. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  58. CONDOMINIUM
    Sealodge C7

    Sealodge C7

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $275/night

  59. CONDOMINIUM
    Sea Village 3-317

    Sea Village 3-317

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $256/night

  60. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  61. CONDOMINIUM
    Sands of Kahana 354

    Sands of Kahana 354

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $471 to $1,128/night

  62. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $588/night

  63. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $153/night

  64. CONDOMINIUM
    Sandpiper 120B

    Sandpiper 120B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $153/night

  65. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  66. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $343 to $452/night

  67. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $136 to $261/night

  68. CONDOMINIUM
    Royal Kahana 409 1 Bdrm

    Royal Kahana 409 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $551/night

  69. CONDOMINIUM
    Royal Kahana 315

    Royal Kahana 315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $204 to $423/night

  70. CONDOMINIUM
    Royal Kahana 220 (2bd / 2ba)

    Royal Kahana 220 (2bd / 2ba)

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $379/night

  71. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $304/night

  72. CONDOMINIUM
    Royal Kahana 119 Studio

    Royal Kahana 119 Studio

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $346/night

  73. CONDOMINIUM
    Royal Kahana 1114 1 Bdrm

    Royal Kahana 1114 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $423/night

  74. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $345/night

  75. CONDOMINIUM
    Royal Kahana 1012

    Royal Kahana 1012

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $551/night

  76. HOUSE
    Riko Hale

    Riko Hale

    Haena, HI

    FREE CANCELLATION

    $249 to $312/night

  77. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    Pool
    FREE CANCELLATION

    $397 to $458/night

  78. CONDOMINIUM
    Puamana 9C

    Puamana 9C

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  79. TOWNHOUSE
    Puamana 52-3

    Puamana 52-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $490/night

  80. TOWNHOUSE
    Puamana 35-2

    Puamana 35-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $611/night

  81. CONDOMINIUM
    Puamana 25B

    Puamana 25B

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $238/night

  82. TOWNHOUSE
    Puamana 25-4

    Puamana 25-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $249/night

  83. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $296/night

  84. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $324/night

  85. TOWNHOUSE
    Puamana 15-3

    Puamana 15-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $449/night

  86. CONDOMINIUM
    Polynesian Shores 111

    Polynesian Shores 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $214 to $413/night

  87. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Pool
    FREE CANCELLATION

    $257 to $361/night

  88. CONDOMINIUM
    Pohailani Maui 115

    Pohailani Maui 115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $320/night

  89. CONDOMINIUM
    Pohailani 131

    Pohailani 131

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $445/night

  90. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  91. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  92. HOUSE
    Plantation Cottage

    Plantation Cottage

    Hanalei, HI

    FREE CANCELLATION

    $374 to $499/night

  93. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  94. CONDOMINIUM
    PentHouse 701

    PentHouse 701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $370/night

  95. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  96. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $531/night

  97. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $220 to $363/night

  98. CONDOMINIUM
    Papakea G301

    Papakea G301

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $299/night

  99. CONDOMINIUM
    Papakea A108

    Papakea A108

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  100. CONDOMINIUM
    Palms at Wailea #205

    Palms at Wailea #205

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $317 to $755/night