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. APARTMENT
    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in the Heart

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in th...

    Lahaina, HI

    Pool Hot Tub

    $243 to $551/night

  2. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  3. HOUSE
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  4. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  5. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  6. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  7. CONDOMINIUM
    107

    107

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  8. CONDOMINIUM
    111

    111

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  9. CONDOMINIUM
    113

    113

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  10. CONDOMINIUM
    117

    117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  11. CONDOMINIUM
    123

    123

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  12. CONDOMINIUM
    127

    127

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  13. CONDOMINIUM
    128

    128

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  14. CONDOMINIUM
    130

    130

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  15. CONDOMINIUM
    131

    131

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  16. CONDOMINIUM
    133

    133

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  17. CONDOMINIUM
    135

    135

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  18. CONDOMINIUM
    141

    141

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  19. CONDOMINIUM
    142

    142

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  20. CONDOMINIUM
    144

    144

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  21. CONDOMINIUM
    146

    146

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  22. CONDOMINIUM
    147

    147

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  23. CONDOMINIUM
    152

    152

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  24. CONDOMINIUM
    155

    155

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  25. CONDOMINIUM
    156

    156

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  26. CONDOMINIUM
    163

    163

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  27. CONDOMINIUM
    164

    164

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  28. CONDOMINIUM
    170

    170

    Kihei, HI

    Pool
    FREE CANCELLATION

    $223 to $305/night

  29. CONDOMINIUM
    171

    171

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  30. CONDOMINIUM
    172

    172

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  31. CONDOMINIUM
    173

    173

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  32. CONDOMINIUM
    174

    174

    Kihei, HI

    Pool
    FREE CANCELLATION

    $223 to $305/night

  33. CONDOMINIUM
    176

    176

    Kihei, HI

    Pool
    FREE CANCELLATION

    $223 to $305/night

  34. CONDOMINIUM
    177

    177

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  35. CONDOMINIUM
    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $118 to $267/night

  36. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $114 to $414/night

  37. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  38. CONDOMINIUM
    203

    203

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  39. CONDOMINIUM
    205

    205

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  40. CONDOMINIUM
    206

    206

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  41. CONDOMINIUM
    207

    207

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  42. CONDOMINIUM
    209

    209

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  43. CONDOMINIUM
    213

    213

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  44. CONDOMINIUM
    217

    217

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  45. CONDOMINIUM
    218

    218

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  46. CONDOMINIUM
    220

    220

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  47. CONDOMINIUM
    221

    221

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  48. CONDOMINIUM
    222

    222

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  49. CONDOMINIUM
    223

    223

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  50. CONDOMINIUM
    236

    236

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  51. CONDOMINIUM
    237

    237

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  52. CONDOMINIUM
    240

    240

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  53. CONDOMINIUM
    241

    241

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $297/night

  54. CONDOMINIUM
    245

    245

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  55. CONDOMINIUM
    249

    249

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $363/night

  56. CONDOMINIUM
    252

    252

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  57. CONDOMINIUM
    254

    254

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $393/night

  58. CONDOMINIUM
    258

    258

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  59. CONDOMINIUM
    264

    264

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  60. CONDOMINIUM
    266

    266

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  61. CONDOMINIUM
    268

    268

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  62. CONDOMINIUM
    271

    271

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $393/night

  63. CONDOMINIUM
    273

    273

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  64. CONDOMINIUM
    275

    275

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  65. CONDOMINIUM
    276

    276

    Kihei, HI

    Pool
    FREE CANCELLATION

    $269 to $409/night

  66. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    Pool

    $720 to $2,118/night

  67. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

  68. COTTAGE
    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $134 to $454/night

  69. DUPLEX
    2BR w/ Diamond Head Views & Lanai

    2BR w/ Diamond Head Views & Lanai

    Honolulu, HI

    Pets OK
    FREE CANCELLATION

    $258 to $646/night

  70. 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

  71. CONDOMINIUM
    308

    308

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  72. CONDOMINIUM
    309

    309

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $393/night

  73. CONDOMINIUM
    311

    311

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  74. CONDOMINIUM
    314

    314

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $363/night

  75. CONDOMINIUM
    315

    315

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  76. CONDOMINIUM
    326

    326

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  77. CONDOMINIUM
    327

    327

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $363/night

  78. CONDOMINIUM
    328

    328

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $409/night

  79. CONDOMINIUM
    329

    329

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  80. CONDOMINIUM
    330

    330

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  81. CONDOMINIUM
    333

    333

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $363/night

  82. CONDOMINIUM
    336

    336

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  83. CONDOMINIUM
    338

    338

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  84. CONDOMINIUM
    340

    340

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  85. CONDOMINIUM
    341

    341

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  86. CONDOMINIUM
    342

    342

    Kihei, HI

    Pool
    FREE CANCELLATION

    $235 to $317/night

  87. CONDOMINIUM
    344

    344

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $340/night

  88. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $1,082 to $3,365/night

  89. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $970 to $2,858/night

  90. VILLA
    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $923 to $2,944/night

  91. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Pool Hot Tub

    $1,060 to $3,293/night

  92. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,182 to $3,546/night

  93. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  94. VILLA
    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    Kamuela, HI

    Pool Hot Tub

    $706 to $2,171/night

  95. 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

    $175 to $632/night

  96. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $424/night

  97. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,166 to $3,653/night

  98. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  99. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  100. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night