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. $305 to $390/night

    Kauhale Makai #212

    Kauhale Makai #212

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

    Kauhale Makai #512

    Kauhale Makai #512

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $305 to $390/night

    Kauhale Makai #433

    Kauhale Makai #433

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $305 to $371/night

    Kihei Akahi #DG-02

    Kihei Akahi #DG-02

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  5. $304 to $467/night

    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  6. $304 to $609/night

    Hale Hookaana

    Hale Hookaana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  7. $304 to $568/night

    Beach Villas at Kahalu'u 2-101

    Beach Villas at Kahalu'u 2-101

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  8. $304 to $467/night

    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  9. $304 to $467/night

    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  10. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  11. $304 to $467/night

    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  12. $304 to $467/night

    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  13. $304 to $540/night

    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  14. $304 to $653/night

    Kanaloa 701

    Kanaloa 701

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  15. $304 to $467/night

    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  16. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  17. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  18. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  19. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  20. $304 to $351/night

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    Keauhou Kona Surf and Racquet Club Townhouse# 185

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  21. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  22. $302 to $482/night

    Kanai A Nalu 302

    Kanai A Nalu 302

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  23. $302 to $481/night

    Valley Isle Resort #901 (MAUI)

    Valley Isle Resort #901 (MAUI)

    1 Bedroom0.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  24. $302 to $354/night

    Unit 303

    Unit 303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  25. $302 to $505/night

    ROYAL MAUIAN, #517

    ROYAL MAUIAN, #517

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  26. $302 to $354/night

    Unit 305

    Unit 305

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  27. $302 to $669/night

    Lahaina Shores #501

    Lahaina Shores #501

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $302 to $354/night

    Unit 310

    Unit 310

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  29. $302 to $652/night

    Lai Nani Oceanfront Estate Bungalow #2

    Lai Nani Oceanfront Estate Bungalow #2

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  30. $302 to $354/night

    Unit 311

    Unit 311

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  31. $302 to $505/night

    ROYAL MAUIAN, #516

    ROYAL MAUIAN, #516

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  32. $302 to $438/night

    ROYAL MAUIAN, #219

    ROYAL MAUIAN, #219

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  33. $301 to $580/night

    Hoyochi Nikko 206

    Hoyochi Nikko 206

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $301 to $482/night

    Mauna Kai 7B

    Mauna Kai 7B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $301 to $355/night

    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $300 to $910/night

    Puamana Townhouse 64-1

    Puamana Townhouse 64-1

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $300 to $494/night

    Kapalua Bay Villa 29G5 Ocean Front

    Kapalua Bay Villa 29G5 Ocean Front

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
  38. $300 to $535/night

    Puu Poa 201

    Puu Poa 201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  39. $300 to $480/night

    White Sands Village #201

    White Sands Village #201

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $300 to $813/night

    Paki Maui 424

    Paki Maui 424

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $299 to $488/night

    WAILEA ELUA, #0106

    WAILEA ELUA, #0106

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool Hot Tub
  42. $298 to $354/night

    Sands Of Kahana 134

    Sands Of Kahana 134

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  43. $298 to $350/night

    Maui Parkshore #302

    Maui Parkshore #302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  44. $298 to $568/night

    Kona Makai 2303

    Kona Makai 2303

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool Hot Tub
  45. $298 to $350/night

    Maui Parkshore #401

    Maui Parkshore #401

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  46. $298 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  47. $298 to $350/night

    Maui Parkshore #306

    Maui Parkshore #306

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  48. $298 to $350/night

    Maui Parkshore #312

    Maui Parkshore #312

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  49. $298 to $350/night

    Maui Vista #3420

    Maui Vista #3420

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  50. $298 to $350/night

    Maui Vista #1407

    Maui Vista #1407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  51. $298 to $350/night

    Maui Parkshore #316

    Maui Parkshore #316

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  52. $298 to $350/night

    Maui Vista #1406

    Maui Vista #1406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  53. $297 to $390/night

    Maui Kamaole #C-106

    Maui Kamaole #C-106

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $297 to $390/night

    Maui Kamaole #b-107

    Maui Kamaole #b-107

    1 BedroomBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  55. $297 to $390/night

    Maui Kamaole #i-111

    Maui Kamaole #i-111

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $297 to $390/night

    Maui Kamaole #d-104

    Maui Kamaole #d-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $297 to $390/night

    Maui Kamaole #m-104

    Maui Kamaole #m-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $297 to $396/night

    Sugar Beach #302

    Sugar Beach #302

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $297 to $396/night

    Sugar Beach #301

    Sugar Beach #301

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $296 to $356/night

    Maui Banyan #H-308

    Maui Banyan #H-308

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $296 to $448/night

    KIHEI BEACH, #102

    KIHEI BEACH, #102

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  62. $296 to $356/night

    Maui Banyan #G-406

    Maui Banyan #G-406

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $296 to $447/night

    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. $296 to $580/night

    Papakea #H103

    Papakea #H103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $296 to $448/night

    KIHEI BEACH, #501

    KIHEI BEACH, #501

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  67. $296 to $521/night

    International Colony Club #18

    International Colony Club #18

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  68. $295 to $337/night

    Casa De Emdeko 317

    Casa De Emdeko 317

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  69. $294 to $494/night

    Kapalua Golf Villa 19V1 Gold Ocean View

    Kapalua Golf Villa 19V1 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
  70. $294 to $598/night

    Hale Mali'e

    Hale Mali'e

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  71. $294 to $563/night

    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua Golf Villa 25T4 Gold Ocean View

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  72. $294 to $494/night

    Kapalua Ridge Villa 114 Gold Ocean View

    Kapalua Ridge Villa 114 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  73. $294 to $494/night

    Kapalua Ridge Villa 1721 Gold Ocean View

    Kapalua Ridge Villa 1721 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  74. $294 to $413/night

    Honua kai 437

    Honua kai 437

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  75. $294 to $494/night

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
  76. $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
  77. $294 to $531/night

    Kapalua Bay Villa 15G5 Ocean View

    Kapalua Bay Villa 15G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
  78. $294 to $326/night

    Kahaluu Bay Villas #304

    Kahaluu Bay Villas #304

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  79. $293 to $770/night

    Lahaina Shores Condo 701

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. $293 to $727/night

    Sea Village 1105

    Sea Village 1105

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  81. $292 to $568/night

    Alii Villas C-125

    Alii Villas C-125

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
  82. $292 to $350/night

    Keauhou Kona Surf & Racquet Club #3-101 "Hale Malama Pono"

    Keauhou Kona Surf & Racquet Club #3-101 "Hale M...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  83. $292 to $616/night

    Sea Village 4107

    Sea Village 4107

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  84. $292 to $526/night

    MAALAEA SURF, #C-8

    MAALAEA SURF, #C-8

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  85. $292 to $490/night

    Kona Pacific B409

    Kona Pacific B409

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. $292 to $526/night

    MAALAEA SURF, #G-7

    MAALAEA SURF, #G-7

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  87. $291 to $526/night

    Napili Point B44

    Napili Point B44

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $291 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  89. $291 to $605/night

    ROYAL MAUIAN, #315

    ROYAL MAUIAN, #315

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  90. $291 to $425/night

    WAILEA EKAHI, #33B

    WAILEA EKAHI, #33B

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  91. $290 to $332/night

    Kamaole Sands #01-106

    Kamaole Sands #01-106

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $290 to $332/night

    Kamaole Sands #07-206

    Kamaole Sands #07-206

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  93. $290 to $332/night

    Kamaole Sands #02-205

    Kamaole Sands #02-205

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. $290 to $341/night

    Kahana Reef #207

    Kahana Reef #207

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  95. $290 to $763/night

    Ilikai Tower 409

    Ilikai Tower 409

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  96. $290 to $619/night

    Papakea #G408

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  97. $290 to $525/night

    2BR w/ Diamond Head Views & Lanai

    2BR w/ Diamond Head Views & Lanai

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  98. $290 to $563/night

    Kahana Reef #313

    Kahana Reef #313

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  99. $290 to $600/night

    Papakea #G106

    Papakea #G106

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $290 to $332/night

    Kamaole Sands #07-306

    Kamaole Sands #07-306

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION