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. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    FREE CANCELLATION

    $571 to $1,344/night

  2. HOUSE
    2-302 The Beach Villas at Kahaluu

    2-302 The Beach Villas at Kahaluu

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $536/night

  3. 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

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

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $134 to $454/night

  5. 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

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

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $1,082 to $3,365/night

  7. 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

  8. 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 $2,945/night

  9. 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

  10. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  11. 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

  12. 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

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

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,166 to $3,653/night

  14. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

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

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  16. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  17. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  18. CONDOMINIUM
    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    Lahaina, HI

    FREE CANCELLATION

    $217 to $604/night

  19. CONDOMINIUM
    Aina Nalu Premier Platinum Condo H206

    Aina Nalu Premier Platinum Condo H206

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $591/night

  20. CONDOMINIUM
    Ali'i Kai 4202

    Ali'i Kai 4202

    Princeville, HI

    Pool
    FREE CANCELLATION

    $234 to $424/night

  21. CONDOMINIUM
    Alii Kai 4103

    Alii Kai 4103

    Princeville, HI

    Pool

    $283 to $331/night

  22. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  23. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  24. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  25. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  26. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  27. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $366 to $501/night

  28. CONDOMINIUM
    Bay Villa 38G2

    Bay Villa 38G2

    Lahaina, HI

    Pool

    $248 to $304/night

  29. CONDOMINIUM
    Bay Villa 38G3

    Bay Villa 38G3

    Lahaina, HI

    Pool

    $248 to $304/night

  30. CONDOMINIUM
    Beach Villas M3

    Beach Villas M3

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $480/night

  31. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    Pool Hot Tub
  32. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  33. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  34. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Pool Hot Tub

    $211 to $235/night

  35. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Pool Hot Tub

    $253 to $271/night

  36. 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

  37. APARTMENT
    Condo with Ocean View! Right on a Golf Course & Minutes from the Beach!

    Condo with Ocean View! Right on a Golf Course & Minu...

    Waikoloa, HI

    Pool
    FREE CANCELLATION

    $140 to $213/night

  38. CONDOMINIUM
    Country Club Villas #208

    Country Club Villas #208

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $480/night

  39. CONDOMINIUM
    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    Honolulu, HI

    FREE CANCELLATION

    $178 to $248/night

  40. APARTMENT
    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Honolulu, HI

    FREE CANCELLATION

    $153 to $219/night

  41. CONDOMINIUM
    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    Honolulu, HI

    FREE CANCELLATION

    $309 to $438/night

  42. CONDOMINIUM
    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $141 to $453/night

  43. CONDOMINIUM
    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $146 to $466/night

  44. HOUSE
    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $538/night

  45. HOUSE
    Fairway Villas I34 at the Waikoloa Beach Resort

    Fairway Villas I34 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $538/night

  46. CONDOMINIUM
    Fairway Villas L21 at the Waikoloa Beach Resort

    Fairway Villas L21 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool
    FREE CANCELLATION

    $250 to $495/night

  47. TOWNHOUSE
    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $631/night

  48. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  49. CONDOMINIUM
    Grand Champions 124

    Grand Champions 124

    Kihei, HI

    Pool
    FREE CANCELLATION

    $374 to $624/night

  50. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  51. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  52. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  53. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  54. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  55. CONDOMINIUM
    Hale Mala Hina-245

    Hale Mala Hina-245

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $216 to $330/night

  56. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  57. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  58. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $285/night

  59. CONDOMINIUM
    Hale Ono Loa 120

    Hale Ono Loa 120

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $245 to $747/night

  60. HOUSE
    Hale Poola

    Hale Poola

    Honolulu, HI

    $890 to $1,302/night

  61. HOUSE
    Hale Pulelehua TVNC#1238

    Hale Pulelehua TVNC#1238

    Hanalei, HI

    $797 to $2,222/night

  62. HOUSE
    Hale Pulelehua with Guest House TVNC#1238

    Hale Pulelehua with Guest House TVNC#1238

    Hanalei, HI

    $952 to $2,635/night

  63. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  64. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  65. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $989/night

  66. 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

    $331 to $1,060/night

  67. CONDOMINIUM
    Hali'i Kai at Waikoloa Beach Resort 9F

    Hali'i Kai at Waikoloa Beach Resort 9F

    Waikoloa, HI

    Pool Hot Tub

    $465 to $1,576/night

  68. HOUSE
    Hallor House TVNC #5147

    Hallor House TVNC #5147

    Hanalei, HI

    $482 to $1,016/night

  69. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    Princeville, HI

    Pool Hot Tub

    $422 to $542/night

  70. CONDOMINIUM
    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    Princeville, HI

    Pool Hot Tub

    $301 to $355/night

  71. CONDOMINIUM
    Hanalei Bay Villa #17

    Hanalei Bay Villa #17

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  72. TOWNHOUSE
    Hanalei Bay Villa 11

    Hanalei Bay Villa 11

    Princeville, HI

    $247 to $319/night

  73. TOWNHOUSE
    Hanalei Bay Villa 12

    Hanalei Bay Villa 12

    Princeville, HI

    $259 to $355/night

  74. CONDOMINIUM
    Hanalei Bay Villas #16

    Hanalei Bay Villas #16

    Princeville, HI

    FREE CANCELLATION

    $249 to $312/night

  75. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  76. BUNGALOW
    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    Kailua Kona, HI

    $411 to $720/night

  77. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $264/night

  78. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,677/night

  79. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  80. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $353/night

  81. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $370/night

  82. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  83. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  84. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  85. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  86. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  87. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $608/night

  88. CONDOMINIUM
    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $550 to $1,553/night

  89. CONDOMINIUM
    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $538 to $1,962/night

  90. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Kaanapali, HI

    Pool Hot Tub

    $531 to $1,999/night

  91. CONDOMINIUM
    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3.5b

    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3....

    Kaanapali, HI

    Pool Hot Tub

    $886 to $3,261/night

  92. CONDOMINIUM
    Honua kai- Konea 301 Frontline with BBQ!

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $566 to $2,227/night

  93. CONDOMINIUM
    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Kaanapali, HI

    Pool Hot Tub

    $316 to $1,121/night

  94. CONDOMINIUM
    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b/1b

    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b...

    Kaanapali, HI

    Pool Hot Tub

    $257 to $894/night

  95. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Pool Hot Tub

    $616 to $2,355/night

  96. CONDOMINIUM
    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $406 to $1,543/night

  97. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $825 to $2,810/night

  98. CONDOMINIUM
    Hoyochi Nikko #102

    Hoyochi Nikko #102

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $240 to $437/night

  99. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $201 to $409/night

  100. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night