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. CONDOMINIUM
    Whaler On Kaanapali 763

    Whaler On Kaanapali 763

    Lahaina, HI

    Pool Hot Tub

    $248 to $304/night

  2. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469 to $776/night

  3. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Pool
    FREE CANCELLATION

    $134 to $490/night

  4. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Pool
    FREE CANCELLATION

    $401 to $610/night

  5. CONDOMINIUM
    Wailea Ekolu 1604

    Wailea Ekolu 1604

    Kihei, HI

    Pool
    FREE CANCELLATION

    $249 to $531/night

  6. CONDOMINIUM
    Wailea Ekahi 36C

    Wailea Ekahi 36C

    Wailea, HI

    Pool
    FREE CANCELLATION

    $226 to $549/night

  7. 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

  8. VILLA
    Waikoloa Beach Villas I1

    Waikoloa Beach Villas I1

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $741/night

  9. CONDOMINIUM
    Waikoloa Beach Villas G2

    Waikoloa Beach Villas G2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $476/night

  10. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  11. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  12. CONDOMINIUM
    Vista Waikoloa G-104

    Vista Waikoloa G-104

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  13. CONDOMINIUM
    Vista Waikoloa D-102

    Vista Waikoloa D-102

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  14. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $901/night

  15. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION
  16. CONDOMINIUM
    Valley Isle 902

    Valley Isle 902

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $176 to $388/night

  17. CONDOMINIUM
    Valley Isle 204

    Valley Isle 204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $363/night

  18. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $223 to $312/night

  19. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $158/night

  20. COTTAGE
    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Honolulu, HI

    FREE CANCELLATION

    $147 to $454/night

  21. 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

  22. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  23. CONDOMINIUM
    The Mauna Lani Golf Villas B5

    The Mauna Lani Golf Villas B5

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $741/night

  24. 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

  25. CONDOMINIUM
    Shores at Waikoloa #234 at Bo Tree Tower

    Shores at Waikoloa #234 at Bo Tree Tower

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $464/night

  26. CONDOMINIUM
    Sea Village 3-317

    Sea Village 3-317

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $256/night

  27. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  28. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  29. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  30. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  31. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  32. CONDOMINIUM
    Sands of Kahana 354

    Sands of Kahana 354

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $460 to $1,100/night

  33. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  34. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  35. CONDOMINIUM
    Sands Of Kahana 318

    Sands Of Kahana 318

    Lahaina, HI

    Pool Hot Tub

    $236 to $276/night

  36. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $588/night

  37. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  38. CONDOMINIUM
    Sands Of Kahana 275

    Sands Of Kahana 275

    Lahaina, HI

    Pool Hot Tub

    $444 to $557/night

  39. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  40. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  41. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  42. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  43. CONDOMINIUM
    Sands Of Kahana 122

    Sands Of Kahana 122

    Lahaina, HI

    Pool Hot Tub

    $186 to $219/night

  44. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $136 to $254/night

  45. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $306/night

  46. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $199 to $348/night

  47. HOUSE
    Riko Hale

    Riko Hale

    Haena, HI

    FREE CANCELLATION

    $249 to $312/night

  48. CONDOMINIUM
    Ridge Villa 414

    Ridge Villa 414

    LAHAINA, HI

    Pool Hot Tub

    $332 to $388/night

  49. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  50. CONDOMINIUM
    Ridge Villa 1222

    Ridge Villa 1222

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  51. TOWNHOUSE
    Puamana 52-3

    Puamana 52-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $490/night

  52. TOWNHOUSE
    Puamana 35-2

    Puamana 35-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $249 to $611/night

  53. TOWNHOUSE
    Puamana 25-4

    Puamana 25-4

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $249/night

  54. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $296/night

  55. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $324/night

  56. TOWNHOUSE
    Puamana 15-3

    Puamana 15-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $449/night

  57. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  58. CONDOMINIUM
    Polynesian Shores 111

    Polynesian Shores 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $209 to $413/night

  59. CONDOMINIUM
    Pohailani Maui 152

    Pohailani Maui 152

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $333/night

  60. CONDOMINIUM
    Pohailani Maui 115

    Pohailani Maui 115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $333/night

  61. CONDOMINIUM
    Pohailani 131

    Pohailani 131

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $226 to $528/night

  62. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  63. HOUSE
    Plantation Cottage

    Plantation Cottage

    Hanalei, HI

    FREE CANCELLATION

    $392 to $523/night

  64. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  65. CONDOMINIUM
    PentHouse 701

    PentHouse 701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $187 to $370/night

  66. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  67. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $266 to $531/night

  68. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $215 to $365/night

  69. CONDOMINIUM
    Papakea J107

    Papakea J107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $498/night

  70. CONDOMINIUM
    Papakea G301

    Papakea G301

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $299/night

  71. CONDOMINIUM
    Paki Maui 422

    Paki Maui 422

    Lahaina, HI

    Pool Hot Tub

    $298 to $354/night

  72. CONDOMINIUM
    Paki Maui 415

    Paki Maui 415

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $375/night

  73. CONDOMINIUM
    Paki Maui 316

    Paki Maui 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $125 to $369/night

  74. CONDOMINIUM
    Paki Maui 207

    Paki Maui 207

    Lahaina, HI

    FREE CANCELLATION

    $163 to $281/night

  75. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $431/night

  76. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $454 to $918/night

  77. CONDOMINIUM
    Pacific Shores B414

    Pacific Shores B414

    Kihei, HI

    Pool
    FREE CANCELLATION

    $174 to $333/night

  78. CONDOMINIUM
    Pacific Shores B406

    Pacific Shores B406

    Kihei, HI

    Pool
    FREE CANCELLATION

    $189 to $501/night

  79. CONDOMINIUM
    Pacific Shores B102

    Pacific Shores B102

    Kihei, HI

    Pool
    FREE CANCELLATION

    $281 to $531/night

  80. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  81. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  82. HOUSE
    Ohana House

    Ohana House

    Hanalei, HI

    FREE CANCELLATION

    $499 to $562/night

  83. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $138 to $316/night

  84. CONDOMINIUM
    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $378/night

  85. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  86. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  87. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $381/night

  88. CONDOMINIUM
    Noelani 304 3bdrm 2.5 bath

    Noelani 304 3bdrm 2.5 bath

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $487 to $680/night

  89. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  90. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  91. CONDOMINIUM
    Nihilani 28C

    Nihilani 28C

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $374/night

  92. HOUSE
    New Listing! “Kona Sunset Hale” w/ Ocean Views

    New Listing! “Kona Sunset Hale” w/ Ocean Views

    Kailua Kona, HI

    FREE CANCELLATION

    $166 to $604/night

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

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

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $343/night

  94. HOUSE
    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $219 to $600/night

  95. CONDOMINIUM
    Napili Shores E240

    Napili Shores E240

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $299/night

  96. CONDOMINIUM
    Napili Shores D230

    Napili Shores D230

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $295/night

  97. CONDOMINIUM
    Napili Shores D227

    Napili Shores D227

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $324/night

  98. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $163 to $265/night

  99. CONDOMINIUM
    Napili Shores C116

    Napili Shores C116

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $286/night

  100. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $471/night