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
    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

    $139 to $445/night

  2. 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

    $203 to $632/night

  3. 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 $424/night

  4. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  5. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  6. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  7. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    FREE CANCELLATION

    $304 to $467/night

  8. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $128 to $489/night

  9. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  10. CONDOMINIUM
    B2-1 Bedroom Oceanfront

    B2-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  11. CONDOMINIUM
    Beach Villas M3

    Beach Villas M3

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $165 to $481/night

  12. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  13. CONDOMINIUM
    C1-2 Bedroom Oceanfront

    C1-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  14. CONDOMINIUM
    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  15. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  16. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  17. 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

  18. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $464/night

  19. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  20. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  21. CONDOMINIUM
    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  22. CONDOMINIUM
    D3-1 Bedroom Beachfront

    D3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  23. CONDOMINIUM
    D4-1 Bedroom Beachfront

    D4-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  24. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  25. CONDOMINIUM
    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  26. CONDOMINIUM
    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  27. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  28. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  29. CONDOMINIUM
    Fairway Villas #K1 at the Waikoloa Beach Resort

    Fairway Villas #K1 at the Waikoloa Beach Resort

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $269 to $708/night

  30. 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

    $143 to $453/night

  31. 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

    $125 to $466/night

  32. 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

  33. 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

  34. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  35. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  36. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  37. CONDOMINIUM
    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  38. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  39. CONDOMINIUM
    H2-1 Bedroom Beachfront

    H2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  40. CONDOMINIUM
    H3-1 Bedroom Beachfront

    H3-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  41. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  42. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  43. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  44. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Pool Hot Tub

    $362 to $1,204/night

  45. CONDOMINIUM
    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $386 to $1,125/night

  46. CONDOMINIUM
    Hali'i Kai at Waikoloa 2B

    Hali'i Kai at Waikoloa 2B

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $617/night

  47. CONDOMINIUM
    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Princeville, HI

    Pool
    FREE CANCELLATION

    $220 to $238/night

  48. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Pool
    FREE CANCELLATION

    $520 to $581/night

  49. CONDOMINIUM
    Hanalei Bay Resort 5202

    Hanalei Bay Resort 5202

    Princeville, HI

    Pool
    FREE CANCELLATION

    $361 to $410/night

  50. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  51. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  52. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  53. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  54. CONDOMINIUM
    Kamaole Sands #1-103

    Kamaole Sands #1-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $278/night

  55. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  56. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $383/night

  57. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $348/night

  58. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $249 to $596/night

  59. CONDOMINIUM
    Kamaole Sands #2-301

    Kamaole Sands #2-301

    Kihei, HI

    Pool
    FREE CANCELLATION

    $283 to $644/night

  60. CONDOMINIUM
    Kamaole Sands #2-306

    Kamaole Sands #2-306

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $347/night

  61. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $560/night

  62. CONDOMINIUM
    Kamaole Sands #4-408

    Kamaole Sands #4-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $406/night

  63. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $360/night

  64. CONDOMINIUM
    Kamaole Sands #6-108

    Kamaole Sands #6-108

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $151 to $360/night

  65. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $365/night

  66. CONDOMINIUM
    Kamaole Sands #7-305

    Kamaole Sands #7-305

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $179 to $430/night

  67. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $637/night

  68. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $273/night

  69. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $625 to $844/night

  70. CONDOMINIUM
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    Pool

    $781 to $1,219/night

  71. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  72. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    Kapolei, HI

    Pool Hot Tub
  73. CONDOMINIUM
    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $625 to $1,655/night

  74. CONDOMINIUM
    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $438 to $1,358/night

  75. CONDOMINIUM
    Kona 2 Bedroom

    Kona 2 Bedroom

    Kailua-Kona, HI

    Pool Hot Tub
  76. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  77. CONDOMINIUM
    Kona Pacific

    Kona Pacific

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $146 to $183/night

  78. TOWNHOUSE
    Kulalani at Mauna Lani #405

    Kulalani at Mauna Lani #405

    Kamuela, HI

    Pool
    FREE CANCELLATION

    $401 to $944/night

  79. CONDOMINIUM
    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $110 to $260/night

  80. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $156 to $633/night

  81. CONDOMINIUM
    Maui Ka'anapali Villas Studio Premier Condo A417

    Maui Ka'anapali Villas Studio Premier Condo A417

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $372 to $636/night

  82. CONDOMINIUM
    Maui Kamaole #G-210

    Maui Kamaole #G-210

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $377 to $493/night

  83. CONDOMINIUM
    Maui Kamaole #I-215

    Maui Kamaole #I-215

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $377/night

  84. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $459/night

  85. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $266/night

  86. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  87. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $478/night

  88. TOWNHOUSE
    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $651/night

  89. CONDOMINIUM
    Mauna Lani Terrace K301

    Mauna Lani Terrace K301

    Kamuela, HI

    Pool
    FREE CANCELLATION

    $340 to $644/night

  90. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  91. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  92. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  93. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $381/night

  94. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

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

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $378/night

  96. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $108 to $316/night

  97. CONDOMINIUM
    Palm Villa I3 at the Mauna Lani Resort

    Palm Villa I3 at the Mauna Lani Resort

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $225 to $793/night

  98. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  99. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  100. CONDOMINIUM
    Plantations at Princeville #111

    Plantations at Princeville #111

    Princeville, HI

    Pool

    $206 to $311/night