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
    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $464/night

  2. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  3. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  4. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Pool
    FREE CANCELLATION

    $488 to $581/night

  5. CONDOMINIUM
    Kihei Kai Nani #4-221

    Kihei Kai Nani #4-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $219/night

  6. CONDOMINIUM
    International Colony Club #18

    International Colony Club #18

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $566/night

  7. CONDOMINIUM
    Vista Waikoloa G-104

    Vista Waikoloa G-104

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  8. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $174 to $299/night

  9. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $221/night

  10. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  11. CONDOMINIUM
    Lahaina Roads 309

    Lahaina Roads 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $213 to $438/night

  12. CONDOMINIUM
    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua, HI

    Pool

    $294 to $494/night

  13. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  14. CONDOMINIUM
    Maui Banyan #Q-403A

    Maui Banyan #Q-403A

    Kihei, HI

    FREE CANCELLATION

    $128 to $232/night

  15. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  16. 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

  17. CONDOMINIUM
    Maui Kamaole #J-221

    Maui Kamaole #J-221

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $463/night

  18. CONDOMINIUM
    Kihei Bay Surf #226

    Kihei Bay Surf #226

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  19. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  20. CONDOMINIUM
    Haleakala Shores #B-309

    Haleakala Shores #B-309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $184 to $331/night

  21. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  22. CONDOMINIUM
    Kaleialoha #413

    Kaleialoha #413

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $413/night

  23. CONDOMINIUM
    HOL #216

    HOL #216

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $164 to $325/night

  24. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  25. CONDOMINIUM
    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua, HI

    Pool

    $369 to $594/night

  26. CONDOMINIUM
    Royal Kahana 315

    Royal Kahana 315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $430/night

  27. CONDOMINIUM
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Pool

    $563 to $1,031/night

  28. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  29. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $466/night

  30. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  31. CONDOMINIUM
    Kahaluu Bay Villas #304

    Kahaluu Bay Villas #304

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $385/night

  32. 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

  33. 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

  34. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    Kapolei, HI

    Pool Hot Tub

    $362 to $977/night

  35. 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

  36. 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

  37. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  38. CONDOMINIUM
    Palms at Wailea #205

    Palms at Wailea #205

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $345 to $618/night

  39. CONDOMINIUM
    Maui Kamaole #L-202

    Maui Kamaole #L-202

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $304 to $522/night

  40. CONDOMINIUM
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Pool
    FREE CANCELLATION

    $148 to $183/night

  41. CONDOMINIUM
    Hololani A303

    Hololani A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $499/night

  42. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $625/night

  43. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $498/night

  44. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $384/night

  45. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  46. CONDOMINIUM
    Maui Vista #2-213

    Maui Vista #2-213

    Kihei, HI

    Pool
    FREE CANCELLATION

    $133 to $231/night

  47. CONDOMINIUM
    Wailea Ekolu #805

    Wailea Ekolu #805

    Wailea, HI

    Pool
    FREE CANCELLATION

    $249 to $481/night

  48. 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

  49. CONDOMINIUM
    Puamana 25B

    Puamana 25B

    Princeville, HI

    Pool
    FREE CANCELLATION

    $183 to $238/night

  50. CONDOMINIUM
    Alii Kai II 8H

    Alii Kai II 8H

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $182 to $260/night

  51. CONDOMINIUM
    Hale Ono Loa 101

    Hale Ono Loa 101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $149 to $454/night

  52. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $500/night

  53. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $148 to $321/night

  54. CONDOMINIUM
    Royal Kahana 618

    Royal Kahana 618

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $128 to $249/night

  55. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $435/night

  56. CONDOMINIUM
    Maui Kai 605

    Maui Kai 605

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $336/night

  57. CONDOMINIUM
    Kaanapali Shores 836

    Kaanapali Shores 836

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $330/night

  58. CONDOMINIUM
    Hololani A701

    Hololani A701

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $199 to $474/night

  59. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $294/night

  60. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $264/night

  61. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $185 to $435/night

  62. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $306/night

  63. TOWNHOUSE
    Puamana 15-3

    Puamana 15-3

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $224 to $449/night

  64. CONDOMINIUM
    Kaanapali Royal J202

    Kaanapali Royal J202

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $865/night

  65. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $160 to $304/night

  66. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  67. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  68. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  69. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $409/night

  70. 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

  71. CONDOMINIUM
    Kaleialoha 202

    Kaleialoha 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $336/night

  72. CONDOMINIUM
    HOL 311

    HOL 311

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $348/night

  73. CONDOMINIUM
    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $157 to $277/night

  74. HOUSE
    Hale Kalani

    Hale Kalani

    Wainiha, HI

    FREE CANCELLATION

    $623 to $748/night

  75. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $358/night

  76. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $158 to $239/night

  77. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $523/night

  78. CONDOMINIUM
    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $484/night

  79. 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

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

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  81. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  82. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $134 to $239/night

  83. CONDOMINIUM
    Kahana Reef 303

    Kahana Reef 303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $124 to $320/night

  84. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  85. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $370/night

  86. CONDOMINIUM
    Kaanapali Shores 628

    Kaanapali Shores 628

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $271/night

  87. CONDOMINIUM
    Kaleialoha #113

    Kaleialoha #113

    LAHAINA, HI

    Pool
    FREE CANCELLATION

    $218 to $466/night

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

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $350 to $861/night

  89. CONDOMINIUM
    Polynesian Shores 111

    Polynesian Shores 111

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $168 to $360/night

  90. CONDOMINIUM
    Kihei Bay Surf #126

    Kihei Bay Surf #126

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  91. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $111 to $281/night

  92. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $306 to $648/night

  93. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  94. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $409/night

  95. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Pool Hot Tub

    $286 to $478/night

  96. CONDOMINIUM
    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $220 to $238/night

  97. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $291/night

  98. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $197 to $277/night

  99. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  100. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    FREE CANCELLATION

    $481 to $896/night