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. CONDOMINIUM
    Wailea Elua Unit #0105

    Wailea Elua Unit #0105

    Wailea, HI

    Pool Hot Tub

    $459 to $953/night

  2. CONDOMINIUM
    Wailea Elua Unit #801

    Wailea Elua Unit #801

    Wailea, HI

    Pool Hot Tub

    $459 to $953/night

  3. CONDOMINIUM
    Wailea Elua Unit #0802

    Wailea Elua Unit #0802

    Wailea, HI

    Pool Hot Tub

    $437 to $953/night

  4. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    Pool Hot Tub

    $481 to $1,285/night

  5. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    Pool Hot Tub

    $482 to $839/night

  6. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,487/night

  7. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  8. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  9. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  10. CONDOMINIUM
    Kona Reef #D31

    Kona Reef #D31

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $754/night

  11. ESTATE
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    Pool Hot Tub

    $3,695 to $6,075/night

  12. 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

    $503 to $1,957/night

  13. 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

    $853 to $3,251/night

  14. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  15. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  16. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  17. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  18. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  19. CONDOMINIUM
    Plantation 1111

    Plantation 1111

    Princeville, HI

    Pool Hot Tub

    $241 to $271/night

  20. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  21. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  22. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  23. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  24. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  25. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $413/night

  26. CONDOMINIUM
    Pali Ke Kua 10

    Pali Ke Kua 10

    Princeville, HI

    Pool Hot Tub

    $241 to $283/night

  27. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    Pool Hot Tub

    $235 to $301/night

  28. CONDOMINIUM
    Pali Ke Kua 203

    Pali Ke Kua 203

    Princeville, HI

    Pool Hot Tub

    $362 to $422/night

  29. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $109 to $153/night

  30. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,917 to $5,992/night

  31. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  32. 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

    $254 to $908/night

  33. CONDOMINIUM
    Sea Village 4107

    Sea Village 4107

    Kailua Kona, HI

    Pool Hot Tub

    $281 to $800/night

  34. 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

    $937 to $3,933/night

  35. CONDOMINIUM
    Mauna Lani Terrace A303

    Mauna Lani Terrace A303

    Kamuela, HI

    Pool Hot Tub

    $899 to $1,553/night

  36. CONDOMINIUM
    Sugar Beach Resort, #329

    Sugar Beach Resort, #329

    Kihei, HI

    Pool Hot Tub

    $202 to $387/night

  37. CONDOMINIUM
    Sugar Beach Resort, #414

    Sugar Beach Resort, #414

    Kihei, HI

    Pool Hot Tub

    $202 to $387/night

  38. CONDOMINIUM
    Sugar Beach Resort, #518

    Sugar Beach Resort, #518

    Kihei, HI

    Pool Hot Tub

    $190 to $387/night

  39. CONDOMINIUM
    Wailea Elua, #2003

    Wailea Elua, #2003

    Wailea, HI

    Pool Hot Tub

    $448 to $823/night

  40. CONDOMINIUM
    Wailea Elua Unit #2106

    Wailea Elua Unit #2106

    Wailea, HI

    Pool Hot Tub

    $448 to $897/night

  41. 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

  42. 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

  43. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  44. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/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

    $1,060 to $3,293/night

  46. CONDOMINIUM
    Kona Reef #D22

    Kona Reef #D22

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $375 to $1,294/night

  47. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $154 to $688/night

  48. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $316 to $1,118/night

  49. 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

    $608 to $2,348/night

  50. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $370/night

  51. 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

  52. 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

  53. CONDOMINIUM
    Maui El Dorado J218

    Maui El Dorado J218

    LAHAINA, HI

    Pool Hot Tub

    $208 to $259/night

  54. CONDOMINIUM
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  55. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  56. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  57. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  58. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  59. CONDOMINIUM
    Kamahana 18

    Kamahana 18

    Princeville, HI

    Pool Hot Tub

    $223 to $277/night

  60. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  61. CONDOMINIUM
    Villas of Kamalii 37

    Villas of Kamalii 37

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $182 to $336/night

  62. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  63. CONDOMINIUM
    Hanalei Bay Resort 6302

    Hanalei Bay Resort 6302

    Princeville, HI

    Pool Hot Tub

    $301 to $355/night

  64. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  65. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Pool Hot Tub

    $211 to $235/night

  66. CONDOMINIUM
    The Montage Kapalua Bay- Heliconia 2302- Ocean View Paradise!

    The Montage Kapalua Bay- Heliconia 2302- Ocean View Para...

    Kapalua, HI

    Pool Hot Tub

    $1,183 to $4,264/night

  67. 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

  68. CONDOMINIUM
    Pali Ke Kua 115

    Pali Ke Kua 115

    Princeville, HI

    Pool Hot Tub

    $259 to $301/night

  69. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  70. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  71. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  72. CONDOMINIUM
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $145 to $182/night

  73. 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

  74. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  75. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759/night

  76. CONDOMINIUM
    Makahuena 2202

    Makahuena 2202

    Koloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $694/night

  77. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $829/night

  78. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  79. 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

    $399 to $1,539/night

  80. 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 $1,118/night

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

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,668/night

  82. CONDOMINIUM
    Kauai Beach Villas 1 Bedroom

    Kauai Beach Villas 1 Bedroom

    Lihue, HI

    Pool Hot Tub

    $209/night

  83. CONDOMINIUM
    Makena Surf Resort, #G-201

    Makena Surf Resort, #G-201

    Kihei, HI

    Pool Hot Tub

    $775 to $1,094/night

  84. CONDOMINIUM
    Sugar Beach Resort, #121

    Sugar Beach Resort, #121

    Kihei, HI

    Pool Hot Tub

    $202 to $387/night

  85. CONDOMINIUM
    Sugar Beach Resort, #130

    Sugar Beach Resort, #130

    Kihei, HI

    Pool Hot Tub

    $190 to $387/night

  86. CONDOMINIUM
    Sugar Beach Resort, #330

    Sugar Beach Resort, #330

    Kihei, HI

    Pool Hot Tub

    $202 to $387/night

  87. CONDOMINIUM
    Wailea Elua Unit #0307

    Wailea Elua Unit #0307

    Wailea, HI

    Pool Hot Tub

    $459 to $953/night

  88. CONDOMINIUM
    Wailea Elua Unit #2107

    Wailea Elua Unit #2107

    Wailea, HI

    Pool Hot Tub

    $448 to $897/night

  89. CONDOMINIUM
    Ke Nani Kai Condo 260

    Ke Nani Kai Condo 260

    Maunaloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $169/night

  90. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    Pool Hot Tub

    $393 to $1,336/night

  91. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $2,199/night

  92. HOUSE
    Keauhou Estates #185

    Keauhou Estates #185

    Kailua Kona, HI

    Hot Tub

    $482 to $780/night

  93. CONDOMINIUM
    Valley Isle Resort #901 (MAUI)

    Valley Isle Resort #901 (MAUI)

    Lahaina, HI

    Pool Hot Tub

    $302 to $481/night

  94. CONDOMINIUM
    Kona Reef #A33

    Kona Reef #A33

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $550/night

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

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

    Kaanapali, HI

    Pool Hot Tub

    $495 to $1,646/night

  96. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Pool Hot Tub

    $825 to $2,802/night

  97. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  98. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  99. 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

    $522 to $1,992/night

  100. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  101. CONDOMINIUM
    Ridge Villa 1222

    Ridge Villa 1222

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  102. CONDOMINIUM
    Sands Of Kahana 134

    Sands Of Kahana 134

    Lahaina, HI

    Pool Hot Tub

    $298 to $354/night

  103. CONDOMINIUM
    Pali Ke Kua 15

    Pali Ke Kua 15

    Princeville, HI

    Pool Hot Tub

    $241 to $283/night

  104. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  105. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  106. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  107. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    Princeville, HI

    Pool Hot Tub

    $422 to $542/night

  108. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $182 to $257/night

  109. CONDOMINIUM
    Pali Ke Kua 121

    Pali Ke Kua 121

    Princeville, HI

    Pool Hot Tub

    $362 to $422/night

  110. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  111. 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

    $220 to $424/night

  112. CONDOMINIUM
    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $218 to $540/night

  113. 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

  114. CONDOMINIUM
    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  115. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Pool Hot Tub

    $253 to $271/night

  116. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  117. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  118. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $401/night

  119. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $239 to $401/night

  120. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $391 to $1,245/night

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

    Honua kai- Konea 301 Frontline with BBQ!

    Kaanapali, HI

    Pool Hot Tub

    $535 to $2,056/night

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

    Hali'i Kai at Waikoloa Beach Resort 9F

    Waikoloa, HI

    Pool Hot Tub

    $424 to $1,572/night