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
    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Honolulu, HI

    FREE CANCELLATION

    $153 to $219/night

  2. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  3. HOUSE
    Makalae

    Makalae

    Koloa, HI

    $1,303 to $1,453/night

  4. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool

    $456 to $654/night

  5. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool

    $299 to $452/night

  6. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,267/night

  7. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,031/night

  8. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool

    $259 to $361/night

  9. CONDOMINIUM
    Kihei Akahi Resort- Unit C405

    Kihei Akahi Resort- Unit C405

    Kihei, HI

    Pool
    FREE CANCELLATION

    $161 to $353/night

  10. CONDOMINIUM
    Grand Champions 124

    Grand Champions 124

    Kihei, HI

    Pool
    FREE CANCELLATION

    $269 to $594/night

  11. CONDOMINIUM
    Maui Kai 201

    Maui Kai 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $585/night

  12. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  13. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  14. CONDOMINIUM
    Kahana Sunset E8

    Kahana Sunset E8

    Lahaina, HI

    Pool

    $276 to $332/night

  15. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $330/night

  16. CONDOMINIUM
    Kahana Sunset D2D

    Kahana Sunset D2D

    Lahaina, HI

    Pool

    $186 to $270/night

  17. CONDOMINIUM
    Maui Kai 506

    Maui Kai 506

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $411/night

  18. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  19. CONDOMINIUM
    Kahana Sunset B1

    Kahana Sunset B1

    Lahaina, HI

    Pool

    $253 to $309/night

  20. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  21. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  22. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  23. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $132 to $304/night

  24. HOUSE
    NEW! Punahele Point

    NEW! Punahele Point

    Princeville, HI

    $775 to $1,291/night

  25. HOUSE
    Pu'uwai Hale

    Pu'uwai Hale

    Princeville, HI

    $1,152 to $1,645/night

  26. CONDOMINIUM
    Kahana Sunset B5B

    Kahana Sunset B5B

    Lahaina, HI

    Pool

    $214 to $270/night

  27. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  28. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  29. CONDOMINIUM
    Kona Pacific B511

    Kona Pacific B511

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $158 to $203/night

  30. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  31. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  32. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Pool
    FREE CANCELLATION

    $257 to $361/night

  33. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  34. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  35. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night

  36. CONDOMINIUM
    Kahana Sunset B8

    Kahana Sunset B8

    Lahaina, HI

    Pool

    $309 to $366/night

  37. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  38. 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

    $934 to $2,945/night

  39. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  40. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  41. CONDOMINIUM
    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $225/night

  42. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool

    $456 to $572/night

  43. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool

    $270 to $338/night

  44. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  45. 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

    $977 to $3,081/night

  46. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,605/night

  47. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Pool

    $314 to $661/night

  48. CONDOMINIUM
    117

    117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  49. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  50. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $161 to $361/night

  51. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $264/night

  52. 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

  53. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $452 to $926/night

  54. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $158 to $191/night

  55. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $295/night

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

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $363/night

  57. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $276 to $332/night

  58. 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

  59. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  60. CONDOMINIUM
    Kahana Sunset B7

    Kahana Sunset B7

    Lahaina, HI

    Pool

    $309 to $366/night

  61. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  62. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  63. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  64. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  65. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  66. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  67. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  68. CONDOMINIUM
    Mauna Kai 2

    Mauna Kai 2

    Princeville, HI

    $357 to $741/night

  69. CONDOMINIUM
    Kahana Sunset B3B

    Kahana Sunset B3B

    Lahaina, HI

    Pool

    $186 to $214/night

  70. 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 $934/night

  71. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  72. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $229 to $624/night

  73. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  74. CONDOMINIUM
    Kahana Sunset C7

    Kahana Sunset C7

    Lahaina, HI

    Pool

    $276 to $332/night

  75. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  76. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  77. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  78. CONDOMINIUM
    Kahana Sunset D8

    Kahana Sunset D8

    Lahaina, HI

    Pool

    $276 to $332/night

  79. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    Pool
    FREE CANCELLATION

    $196 to $221/night

  80. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  81. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $370/night

  82. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  83. CONDOMINIUM
    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $118 to $263/night

  84. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  85. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  86. CONDOMINIUM
    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    Kapaa, HI

    Pool Hot Tub

    $322 to $426/night

  87. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $1,910/night

  88. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    Pool Hot Tub

    $393 to $1,062/night

  89. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  90. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  91. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  92. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  93. CONDOMINIUM
    Kaanapali Plantation #59

    Kaanapali Plantation #59

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $146 to $375/night

  94. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  95. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $361 to $479/night

  96. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  97. 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 $448/night

  98. CONDOMINIUM
    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

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

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $110 to $459/night

  100. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $770/night