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. $171 to $443/night

    Kaleialoha #305

    Kaleialoha #305

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $208 to $347/night

    Menehune Shores #401

    Menehune Shores #401

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  3. $150 to $219/night

    Kihei Kai Nani #4-221

    Kihei Kai Nani #4-221

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $269 to $409/night

    276

    276

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  5. $234 to $464/night

    Vista Waikoloa G-104

    Vista Waikoloa G-104

    2 Bedrooms2.5 BathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  6. $390 to $488/night

    Maui Banyan #G-201

    Maui Banyan #G-201

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $428 to $546/night

    Maui Kamaole #C-209

    Maui Kamaole #C-209

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $390 to $488/night

    Maui Banyan #F-206

    Maui Banyan #F-206

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $370 to $474/night

    Maui Kamaole #l-209

    Maui Kamaole #l-209

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $82 to $145/night

    Discovery Bay 1815

    Discovery Bay 1815

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  11. $296 to $566/night

    International Colony Club #18

    International Colony Club #18

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  12. $501 to $557/night

    Sands Of Kahana 474

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  13. $174 to $299/night

    Eldorado J111

    Eldorado J111

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  14. $276 to $332/night

    Kahana Sunset D2

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  15. $849 to $1,169/night

    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $305 to $371/night

    Kihei Akahi #DG-02

    Kihei Akahi #DG-02

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  17. $393 to $480/night

    Kamaole Sands #10-405

    Kamaole Sands #10-405

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $347 to $695/night

    Maui Hill #I-99

    Maui Hill #I-99

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  19. $213 to $438/night

    Lahaina Roads 309

    Lahaina Roads 309

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  20. $294 to $494/night

    Kapalua Ridge Villa 1511 Gold Ocean View

    Kapalua Ridge Villa 1511 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  21. $178 to $228/night

    Pohailani 128

    Pohailani 128

    1 Bedroom BathroomSleeps 5
    5 nights minstay
    Pool
  22. $180 to $209/night

    Shores of Maui #124

    Shores of Maui #124

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $297 to $390/night

    Maui Kamaole #m-104

    Maui Kamaole #m-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $241 to $279/night

    Maui Vista #1120

    Maui Vista #1120

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  25. $602 to $764/night

    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $211 to $235/night

    Cliffs 6201

    Cliffs 6201

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  27. $274 to $686/night

    Kaanapali Royal N102

    Kaanapali Royal N102

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $556 to $927/night

    Hale Ili Ili #D

    Hale Ili Ili #D

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $312 to $428/night

    Wailea Ekolu #1608

    Wailea Ekolu #1608

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. $102 to $186/night

    Discovery Bay 1309

    Discovery Bay 1309

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  31. $225 to $260/night

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    Turtle Bay Ohana Hale***NUC 90-TVU-0518

    1 BedroomBathroomsSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $181 to $375/night

    Maui Sands Seaside 718

    Maui Sands Seaside 718

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  33. $197 to $248/night

    Ridge Villa 1422

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  34. $267 to $326/night

    Kauhale Makai #627

    Kauhale Makai #627

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $217 to $359/night

    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $256 to $436/night

    Kuleana 622 1Bdrm

    Kuleana 622 1Bdrm

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  37. $243 to $423/night

    Kaanapali Shores 538

    Kaanapali Shores 538

    Studio BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  38. $256 to $577/night

    Aina Nalu C204

    Aina Nalu C204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $161 to $205/night

    RK1309 2240 Kuhio Ave Honolulu THTH-PTO-ACH-00

    RK1309 2240 Kuhio Ave Honolulu THTH-PTO-ACH-00

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. $331 to $422/night

    Plantation 222

    Plantation 222

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  41. $241 to $271/night

    Plantation 1211

    Plantation 1211

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  42. $135 to $158/night

    Kepuhi Beach Resort 2222

    Kepuhi Beach Resort 2222

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  43. $146 to $540/night

    Spinnaker 216C

    Spinnaker 216C

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $211 to $286/night

    WB910 201 Ohua Ave Honolulu RFRF-CTOM(GM)-00-ACH

    WB910 201 Ohua Ave Honolulu RFRF-CTOM(GM)-00-ACH

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  45. $162 to $324/night

    Kanai A Nalu #311

    Kanai A Nalu #311

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $208 to $347/night

    Maui Kamaole #K-209

    Maui Kamaole #K-209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $221 to $431/night

    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $88 to $157/night

    Discovery Bay 3220

    Discovery Bay 3220

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  49. $256 to $436/night

    Kuleana 713 1 Bdrm

    Kuleana 713 1 Bdrm

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  50. $161 to $325/night

    Maui Banyan #Q-403A

    Maui Banyan #Q-403A

    Studio BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  51. $141 to $250/night

    Ilikai 1117

    Ilikai 1117

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $146 to $287/night

    Ilikai 1938

    Ilikai 1938

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $236 to $304/night

    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  54. $133 to $226/night

    Kihei Garden Estates #B-201

    Kihei Garden Estates #B-201

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $241 to $279/night

    Maui Vista #3301

    Maui Vista #3301

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  57. $258 to $488/night

    Vista Waikoloa B-302

    Vista Waikoloa B-302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $234 to $476/night

    Waikoloa Beach Villas H32

    Waikoloa Beach Villas H32

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $194 to $407/night

    Waikoloa Beach Villas P32

    Waikoloa Beach Villas P32

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $268 to $336/night

    Hanalei Bay Villa 26

    Hanalei Bay Villa 26

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  61. $301 to $355/night

    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  62. $311 to $429/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  63. $244 to $463/night

    Maui Kamaole #J-221

    Maui Kamaole #J-221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $284 to $405/night

    Maui Kamaole #H-211

    Maui Kamaole #H-211

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  65. $398 to $505/night

    Royal Mauian #303

    Royal Mauian #303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  66. $111 to $159/night

    KV810A 2450 Prince Edward St Honolulu TH-PTO-00-ACH

    KV810A 2450 Prince Edward St Honolulu TH-PTO-00-ACH

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  67. $145 to $231/night

    Maui Vista #2-101

    Maui Vista #2-101

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. $203 to $522/night

    Oceanfront 3BR, Breathtaking Views

    Oceanfront 3BR, Breathtaking Views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  69. $284 to $371/night

    Maui Kamaole #l-110

    Maui Kamaole #l-110

    1 BedroomBathroomsSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $164 to $413/night

    HOL #216

    HOL #216

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  71. $164 to $183/night

    Villas on the Prince 28

    Villas on the Prince 28

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
    FREE CANCELLATION
  72. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  73. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $259 to $301/night

    Pali Ke Kua 115

    Pali Ke Kua 115

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  75. $194 to $431/night

    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $184 to $331/night

    Haleakala Shores #B-309

    Haleakala Shores #B-309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  77. $241 to $301/night

    Cliffs 4202

    Cliffs 4202

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  78. $297 to $396/night

    Sugar Beach #302

    Sugar Beach #302

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $334 to $444/night

    Sugar Beach #115

    Sugar Beach #115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $428 to $546/night

    Maui Kamaole #h-201

    Maui Kamaole #h-201

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  81. $305 to $390/night

    Kauhale Makai #433

    Kauhale Makai #433

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $305 to $390/night

    Kauhale Makai #512

    Kauhale Makai #512

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $344 to $460/night

    Kihei Surfside #613

    Kihei Surfside #613

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  84. $235 to $296/night

    Kihei Akahi #D-414

    Kihei Akahi #D-414

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  85. $267 to $326/night

    Kauhale Makai #331

    Kauhale Makai #331

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. $273 to $463/night

    Wailea Ekolu #1207

    Wailea Ekolu #1207

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  87. $344 to $460/night

    Kihei Surfside #107

    Kihei Surfside #107

    1 Bedroom BathroomSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  88. $235 to $283/night

    Mauna Kai 4

    Mauna Kai 4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  89. $422 to $663/night

    Puu Poa 403

    Puu Poa 403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  90. $781 to $1,219/night

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  91. $1,722 to $3,075/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  92. $174 to $445/night

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

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

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $243 to $368/night

    Royal Kahana 107 1Bdrm

    Royal Kahana 107 1Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $238 to $430/night

    Royal Kahana 315

    Royal Kahana 315

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  95. $185 to $502/night

    Kaleialoha #114

    Kaleialoha #114

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $177 to $502/night

    Kaleialoha #413

    Kaleialoha #413

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  97. $218 to $502/night

    Kaleialoha #204

    Kaleialoha #204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. $237/night

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults only

    Turtle Bay 077 West***NUC 90-TVU-0337 Avail to 2 adults ...

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  99. $324 to $486/night

    Maui Kamaole #J-219

    Maui Kamaole #J-219

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. $284 to $342/night

    Maui Banyan #G-105

    Maui Banyan #G-105

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION