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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. CONDOMINIUM
    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $96 to $359/night

  2. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

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

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $134 to $213/night

  3. CONDOMINIUM
    Aloha Surf Condominium 1412

    Aloha Surf Condominium 1412

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $96 to $359/night

  4. CONDOMINIUM
    Kaanapali Royal E101

    Kaanapali Royal E101

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $583/night

  5. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $625/night

  6. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    Kapolei, HI

    Pool Hot Tub

    $408 to $977/night

  7. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  8. CONDOMINIUM
    Hololani A303

    Hololani A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $499/night

  9. CONDOMINIUM
    Kihei Bay Surf #226

    Kihei Bay Surf #226

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  10. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,938 to $4,750/night

  11. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

  12. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $608/night

  13. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,673/night

  14. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $158 to $239/night

  15. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $128 to $249/night

  16. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  17. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,209/night

  18. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $500/night

  19. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $306/night

  20. CONDOMINIUM
    Alii Kai II 8H

    Alii Kai II 8H

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $260/night

  21. CONDOMINIUM
    Maui Kai 605

    Maui Kai 605

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $336/night

  22. CONDOMINIUM
    Maui Kamaole #J-221

    Maui Kamaole #J-221

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $463/night

  23. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  24. CONDOMINIUM
    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua, HI

    Pool

    $294 to $494/night

  25. CONDOMINIUM
    Royal Kahana 315

    Royal Kahana 315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $430/night

  26. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $304/night

  27. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $321/night

  28. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  29. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  30. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  31. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $675/night

  32. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $358/night

  33. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $125 to $275/night

  34. CONDOMINIUM
    Kaleialoha #413

    Kaleialoha #413

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $177 to $502/night

  35. CONDOMINIUM
    HOL #216

    HOL #216

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $164 to $413/night

  36. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $502/night

  37. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $213 to $624/night

  38. CONDOMINIUM
    Kona Pacific B409

    Kona Pacific B409

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $297 to $356/night

  39. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #3

    Keauhou Kona Surf & Racket Club Townhouse #3

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $244 to $358/night

  40. 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 $934/night

  41. CONDOMINIUM
    Kahaluu Bay Villas #304

    Kahaluu Bay Villas #304

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $385/night

  42. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $302 to $326/night

  43. CONDOMINIUM
    Kona Alii 608

    Kona Alii 608

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $162 to $584/night

  44. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $431/night

  45. CONDOMINIUM
    Kaanapali Royal J202

    Kaanapali Royal J202

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $865/night

  46. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $264/night

  47. CONDOMINIUM
    Kahana Reef 303

    Kahana Reef 303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $320/night

  48. CONDOMINIUM
    Maui Banyan #Q-403A

    Maui Banyan #Q-403A

    Kihei, HI

    FREE CANCELLATION

    $161 to $325/night

  49. CONDOMINIUM
    Kihei Kai Nani #4-221

    Kihei Kai Nani #4-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $219/night

  50. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $370/night

  51. CONDOMINIUM
    Lahaina Roads 309

    Lahaina Roads 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $213 to $438/night

  52. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  53. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $409/night

  54. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $502/night

  55. CONDOMINIUM
    Maui Kamaole #L-202

    Maui Kamaole #L-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $292 to $517/night

  56. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  57. CONDOMINIUM
    Vista Waikoloa G-104

    Vista Waikoloa G-104

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  58. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  59. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $521/night

  60. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $164 to $183/night

  61. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $443/night

  62. CONDOMINIUM
    Puamana 25B

    Puamana 25B

    Princeville, HI

    Pool
    FREE CANCELLATION

    $214 to $245/night

  63. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  64. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  65. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $224/night

  66. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  67. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  68. CONDOMINIUM
    Kihei Kai Nani #113

    Kihei Kai Nani #113

    Kihei, HI

    Pool
    FREE CANCELLATION

    $194 to $433/night

  69. APARTMENT
    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $536/night

  70. APARTMENT
    Fairway Villas I34 at the Waikoloa Beach Resort

    Fairway Villas I34 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $536/night

  71. CONDOMINIUM
    Haleakala Shores #B-309

    Haleakala Shores #B-309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $331/night

  72. CONDOMINIUM
    International Colony Club #18

    International Colony Club #18

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $566/night

  73. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  74. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  75. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  76. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  77. CONDOMINIUM
    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua Ridge Villa 2614 Gold Ocean View

    Kapalua, HI

    Pool

    $525 to $869/night

  78. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $111 to $281/night

  79. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,789/night

  80. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  81. CONDOMINIUM
    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua, HI

    Pool

    $369 to $594/night

  82. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  83. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $144 to $330/night

  84. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $277/night

  85. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $498/night

  86. HOUSE
    Hale Kalani

    Hale Kalani

    Wainiha, HI

    FREE CANCELLATION

    $623 to $748/night

  87. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  88. CONDOMINIUM
    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $464/night

  89. CONDOMINIUM
    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  90. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  91. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  92. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $134 to $239/night

  93. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $498/night

  94. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $500/night

  95. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  96. CONDOMINIUM
    Kuleana 713 1 Bdrm

    Kuleana 713 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $436/night

  97. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

  98. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  99. CONDOMINIUM
    The Plantation #1

    The Plantation #1

    Lahaina, HI

    FREE CANCELLATION

    $329 to $549/night

  100. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION