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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. CONDOMINIUM
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  2. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  3. CONDOMINIUM
    Pohailani 231

    Pohailani 231

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $200 to $741/night

  4. CONDOMINIUM
    Hale Ono Loa 120

    Hale Ono Loa 120

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $175 to $747/night

  5. 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

  6. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  7. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $370/night

  8. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  9. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  10. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  11. CONDOMINIUM
    Kanaloa 2201

    Kanaloa 2201

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $239 to $748/night

  12. CONDOMINIUM
    Kona Bali Kai #415

    Kona Bali Kai #415

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $174 to $480/night

  13. TOWNHOUSE
    Mauna Lani Fairways #803

    Mauna Lani Fairways #803

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $218 to $678/night

  14. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $354 to $1,059/night

  15. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  16. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $240/night

  17. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  18. 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 $614/night

  19. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool Hot Tub

    $456 to $572/night

  20. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $2,113/night

  21. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Kamuela, HI

    Pool Hot Tub

    $10,240 to $12,620/night

  22. HOUSE
    Hale Kanani (Kaua'i) TVNC 1342

    Hale Kanani (Kaua'i) TVNC 1342

    Hanalei, HI

    $595 to $1,360/night

  23. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $295/night

  24. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $573 to $1,344/night

  25. CONDOMINIUM
    Makahuena 2202

    Makahuena 2202

    Koloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $202 to $551/night

  26. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  27. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  28. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $291/night

  29. TOWNHOUSE
    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $650/night

  30. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    $464 to $1,121/night

  31. CONDOMINIUM
    Kahana Sunset B3B

    Kahana Sunset B3B

    Lahaina, HI

    Pool

    $186 to $214/night

  32. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  33. CONDOMINIUM
    Maui El Dorado J218

    Maui El Dorado J218

    LAHAINA, HI

    Pool Hot Tub

    $208 to $259/night

  34. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  35. CONDOMINIUM
    Kahana Sunset D10

    Kahana Sunset D10

    Lahaina, HI

    Pool

    $253 to $309/night

  36. CONDOMINIUM
    Kahana Sunset B7

    Kahana Sunset B7

    Lahaina, HI

    Pool

    $309 to $366/night

  37. 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

  38. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  39. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  40. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $170 to $361/night

  41. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  42. CONDOMINIUM
    Kona Reef #D22

    Kona Reef #D22

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $375 to $1,298/night

  43. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $218 to $624/night

  44. 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

  45. HOUSE
    Hale Hiamoe

    Hale Hiamoe

    Kaunakakai, HI

    FREE CANCELLATION

    $225 to $338/night

  46. HOUSE
    A Ala Hale

    A Ala Hale

    Kaunakakai, HI

    FREE CANCELLATION

    $225 to $309/night

  47. CONDOMINIUM
    Ke Nani Kai 218

    Ke Nani Kai 218

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $169 to $225/night

  48. CONDOMINIUM
    Ke Nani Kai 237

    Ke Nani Kai 237

    Kalua Koi, HI

    Pool
    FREE CANCELLATION

    $152 to $197/night

  49. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  50. 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 $3,083/night

  51. CONDOMINIUM
    Kahana Sunset C7

    Kahana Sunset C7

    Lahaina, HI

    Pool

    $276 to $332/night

  52. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $276 to $332/night

  53. CONDOMINIUM
    Kahana Sunset D8

    Kahana Sunset D8

    Lahaina, HI

    Pool

    $276 to $332/night

  54. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  55. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $336/night

  56. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Pool
    FREE CANCELLATION

    $226 to $257/night

  57. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  58. CONDOMINIUM
    Kanai A Nalu 406

    Kanai A Nalu 406

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $238 to $482/night

  59. CONDOMINIUM
    Pali Ke Kua #103

    Pali Ke Kua #103

    Princeville, HI

    Pool Hot Tub

    $354 to $456/night

  60. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  61. CONDOMINIUM
    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $118 to $263/night

  62. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  63. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  64. 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

  65. CONDOMINIUM
    Turtle Bay Hanalei***TA-147868876801

    Turtle Bay Hanalei***TA-147868876801

    Kahuku, HI

    Pool
    FREE CANCELLATION
  66. CONDOMINIUM
    Kahana Sunset B3

    Kahana Sunset B3

    Lahaina, HI

    Pool

    $253 to $366/night

  67. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  68. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  69. 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

  70. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  71. CONDOMINIUM
    117

    117

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  72. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  73. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $358/night

  74. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Pool Hot Tub

    $211 to $235/night

  75. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  76. CONDOMINIUM
    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    Princeville, HI

    Pool Hot Tub

    $301 to $355/night

  77. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  78. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  79. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  80. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  81. CONDOMINIUM
    Close to the Beach, Shopping and Adventures! 3 Bed Condo

    Close to the Beach, Shopping and Adventures! 3 Bed Condo...

    Kohala Coast, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $426/night

  82. 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

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

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

    Kailua Kona, HI

    Pool

    $809 to $2,505/night

  84. HOUSE
    Lau'lea at the Mauna Lani*

    Lau'lea at the Mauna Lani*

    Kamuela, HI

    Pool Hot Tub

    $1,195 to $4,289/night

  85. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Pool

    $314 to $661/night

  86. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,608/night

  87. HOUSE
    Pair of 2BR Hawaiian Cottages

    Pair of 2BR Hawaiian Cottages

    Honolulu, HI

    FREE CANCELLATION

    $452 to $926/night

  88. CONDOMINIUM
    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    Lahaina, HI

    FREE CANCELLATION

    $217 to $604/night

  89. CONDOMINIUM
    Napili Shores F147

    Napili Shores F147

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $202 to $636/night

  90. CONDOMINIUM
    Aina Nalu Premier Platinum Condo H206

    Aina Nalu Premier Platinum Condo H206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $609/night

  91. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $364 to $1,219/night

  92. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $283 to $1,063/night

  93. CONDOMINIUM
    Sealodge E4

    Sealodge E4

    Princeville, HI

    Pool

    $235 to $301/night

  94. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  95. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  96. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  97. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $253 to $484/night

  98. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  99. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  100. CONDOMINIUM
    Sealodge J3

    Sealodge J3

    Princeville, HI

    Pool
    FREE CANCELLATION

    $124 to $437/night