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. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $632/night

  2. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,668/night

  3. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  4. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  5. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  6. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $381/night

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

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  8. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $239/night

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

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  10. CONDOMINIUM
    Kahana Sunset D10

    Kahana Sunset D10

    Lahaina, HI

    Pool

    $253 to $309/night

  11. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  12. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  13. CONDOMINIUM
    The Plantation #1

    The Plantation #1

    Lahaina, HI

    FREE CANCELLATION

    $329 to $549/night

  14. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  15. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $264/night

  16. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  17. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

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

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,016/night

  19. HOUSE
    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  20. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  21. CONDOMINIUM
    Kahana Sunset B7

    Kahana Sunset B7

    Lahaina, HI

    Pool

    $309 to $366/night

  22. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  23. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  24. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  25. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  26. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $276 to $332/night

  27. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  28. CONDOMINIUM
    Kahana Sunset B3B

    Kahana Sunset B3B

    Lahaina, HI

    Pool

    $186 to $214/night

  29. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  30. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    FREE CANCELLATION

    $181 to $239/night

  31. CONDOMINIUM
    Kahana Sunset C7

    Kahana Sunset C7

    Lahaina, HI

    Pool

    $276 to $332/night

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

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  33. CONDOMINIUM
    Kahana Sunset D8

    Kahana Sunset D8

    Lahaina, HI

    Pool

    $276 to $332/night

  34. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  35. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

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

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,500/night

  37. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  38. 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

  39. 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

  40. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  41. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  42. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

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

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  44. CONDOMINIUM
    Kaleialoha #413

    Kaleialoha #413

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  45. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $325 to $337/night

  46. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $277 to $311/night

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

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $120 to $378/night

  48. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  49. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  50. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  51. CONDOMINIUM
    Keawakapu 208

    Keawakapu 208

    Kihei, HI

    FREE CANCELLATION

    $188 to $406/night

  52. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $331/night

  53. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469 to $746/night

  54. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $310/night

  55. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $283 to $606/night

  56. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $186 to $275/night

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

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,668/night

  58. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Pool Hot Tub

    $644 to $2,357/night

  59. CONDOMINIUM
    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $376 to $1,513/night

  60. CONDOMINIUM
    Honua Kai- Hokulani 836- Ocean Views & Huge Party Lanai! 2b/2b

    Honua Kai- Hokulani 836- Ocean Views & Huge Party La...

    Kaanapali, HI

    Pool Hot Tub

    $406 to $1,544/night

  61. CONDOMINIUM
    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Kaanapali, HI

    Pool Hot Tub

    $316 to $1,123/night

  62. CONDOMINIUM
    Hear the Waves!! Honua Kai- Hokulani 306

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    Pool Hot Tub

    $394 to $1,513/night

  63. CONDOMINIUM
    Honua Kai- Hokulani 841- Ocean View! 2b/2b

    Honua Kai- Hokulani 841- Ocean View! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $411 to $3,363/night

  64. CONDOMINIUM
    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $426 to $1,544/night

  65. CONDOMINIUM
    Honua Kai- Konea 642- Ocean View from inside! 2b/2b

    Honua Kai- Konea 642- Ocean View from inside! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $406 to $1,544/night

  66. 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

  67. CONDOMINIUM
    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Lahaina, HI

    Pool Hot Tub

    $394 to $1,449/night

  68. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $633/night

  69. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $489/night

  70. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $165 to $273/night

  71. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Pool
    FREE CANCELLATION

    $401 to $618/night

  72. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  73. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  74. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  75. CONDOMINIUM
    Kahana Sunset C1C

    Kahana Sunset C1C

    Lahaina, HI

    Pool

    $214 to $270/night

  76. CONDOMINIUM
    Kahana Sunset D7

    Kahana Sunset D7

    Lahaina, HI

    Pool

    $276 to $332/night

  77. CONDOMINIUM
    Napili Bay 204

    Napili Bay 204

    Lahaina, HI

    $158 to $203/night

  78. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  79. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  80. CONDOMINIUM
    Kahana Sunset D6

    Kahana Sunset D6

    Lahaina, HI

    Pool

    $276 to $332/night

  81. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  82. CONDOMINIUM
    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $328 to $487/night

  83. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  84. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  85. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  86. HOUSE
    Junior Suite Oceanfront #707

    Junior Suite Oceanfront #707

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $309/night

  87. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  88. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  89. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  90. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  91. CONDOMINIUM
    Villages At Mauna Lani #621

    Villages At Mauna Lani #621

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $370 to $901/night

  92. CONDOMINIUM
    Ridge Villa 414

    Ridge Villa 414

    LAHAINA, HI

    Pool Hot Tub

    $332 to $388/night

  93. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  94. CONDOMINIUM
    Sands Of Kahana 318

    Sands Of Kahana 318

    Lahaina, HI

    Pool Hot Tub

    $236 to $276/night

  95. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  96. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  97. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,384/night

  98. CONDOMINIUM
    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  99. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  100. CONDOMINIUM
    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night