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
    *NEW* Aina Nalu B105: Ground Floor, Quiet Condo in Lively Lahain

    *NEW* Aina Nalu B105: Ground Floor, Quiet Condo in Livel...

    Lahaina, HI

    Pool Hot Tub

    $262 to $593/night

  2. APARTMENT
    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in the Heart

    *NEW* Aina Nalu F201: Top Floor, Hawaiian Hideaway in th...

    Lahaina, HI

    Pool Hot Tub

    $243 to $552/night

  3. 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

  4. 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

  5. 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 $2,943/night

  6. 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

  7. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  8. VILLA
    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    Kamuela, HI

    Pool Hot Tub

    $706 to $2,173/night

  9. 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

  10. 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

  11. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  12. 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

    $157 to $489/night

  13. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  14. CONDOMINIUM
    Aina Nalu B106- Extremely Rare Unit

    Aina Nalu B106- Extremely Rare Unit

    Lahaina, HI

    Pool Hot Tub

    $262 to $737/night

  15. CONDOMINIUM
    Aina Nalu B204

    Aina Nalu B204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $577/night

  16. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  17. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $475/night

  18. CONDOMINIUM
    Aina Nalu C204

    Aina Nalu C204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $577/night

  19. CONDOMINIUM
    Aina Nalu D-207: Affordable luxury at it's best!

    Aina Nalu D-207: Affordable luxury at it's best!

    Lahaina, HI

    Pool Hot Tub

    $302 to $1,070/night

  20. CONDOMINIUM
    Aina Nalu G204

    Aina Nalu G204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $454/night

  21. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $504/night

  22. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $239/night

  23. CONDOMINIUM
    Aina Nalu K102

    Aina Nalu K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $449/night

  24. CONDOMINIUM
    Alii Kai II 11B

    Alii Kai II 11B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  25. CONDOMINIUM
    Alii Kai II 8H

    Alii Kai II 8H

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $226 to $257/night

  26. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  27. APARTMENT
    Bamboo 610 Studio Apartment

    Bamboo 610 Studio Apartment

    Honolulu, HI

    Pool Hot Tub
    FREE CANCELLATION
  28. CONDOMINIUM
    Banyan Tree 404D

    Banyan Tree 404D

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION
  29. APARTMENT
    BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH

    BB809 2425 Kuhio Ave Honolulu DLDL-CTOQ(TC)-MFLH-ACH

    Honolulu, HI

    Pool Hot Tub
    FREE CANCELLATION

    $118 to $174/night

  30. HOUSE
    Beautiful Resort! Close to Beaches! Pool & Hot Tub! Fairway Villas Unit N-3

    Beautiful Resort! Close to Beaches! Pool & Hot Tub! ...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $303/night

  31. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  32. CONDOMINIUM
    Casa De Emdeko 338

    Casa De Emdeko 338

    Kailua-Kona, HI

    Pool Hot Tub

    $251 to $327/night

  33. CONDOMINIUM
    Cliffs 1206

    Cliffs 1206

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  34. CONDOMINIUM
    Cliffs 4202

    Cliffs 4202

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  35. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    Pool Hot Tub

    $235 to $301/night

  36. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  37. CONDOMINIUM
    Cliffs 4209

    Cliffs 4209

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $637/night

  38. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    Pool Hot Tub

    $211 to $259/night

  39. CONDOMINIUM
    Cliffs 5205

    Cliffs 5205

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $96 to $667/night

  40. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Pool Hot Tub

    $211 to $235/night

  41. CONDOMINIUM
    Cliffs 6301

    Cliffs 6301

    Princeville, HI

    Pool Hot Tub

    $271 to $392/night

  42. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  43. CONDOMINIUM
    Cliffs 8205

    Cliffs 8205

    Princeville, HI

    Pool Hot Tub

    $253 to $301/night

  44. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Pool Hot Tub

    $253 to $271/night

  45. 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

  46. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  47. 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

  48. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  49. CONDOMINIUM
    Eldorado E104

    Eldorado E104

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $215 to $480/night

  50. CONDOMINIUM
    Eldorado J109

    Eldorado J109

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $299/night

  51. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $615/night

  52. CONDOMINIUM
    Eldorado K203

    Eldorado K203

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $500/night

  53. CONDOMINIUM
    Emmalani Court 411

    Emmalani Court 411

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $108 to $776/night

  54. CONDOMINIUM
    Exceptional Value for Family! Beautiful Views, Sunsets & Minutes from the Beach!

    Exceptional Value for Family! Beautiful Views, Sunsets &...

    Waikoloa Village, HI

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $286/night

  55. CONDOMINIUM
    Fairway Villas A-31

    Fairway Villas A-31

    WAIKOLOA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $244/night

  56. 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

  57. 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

  58. 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

  59. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  60. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $407/night

  61. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  62. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $213/night

  63. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  64. CONDOMINIUM
    Grand Champions #151

    Grand Champions #151

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $172 to $412/night

  65. CONDOMINIUM
    Grand Champions #45

    Grand Champions #45

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $233 to $557/night

  66. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $233 to $557/night

  67. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $470/night

  68. CONDOMINIUM
    Grand Champions #65

    Grand Champions #65

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $464/night

  69. CONDOMINIUM
    Grand Champions #86

    Grand Champions #86

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $215 to $325/night

  70. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  71. HOUSE
    Hale Alaula- Ocean View

    Hale Alaula- Ocean View

    Kailua Kona, HI

    Hot Tub

    $396 to $1,041/night

  72. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  73. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    Hot Tub

    $631 to $1,693/night

  74. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  75. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  76. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,384/night

  77. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  78. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  79. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Pool Hot Tub

    $513 to $1,668/night

  80. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    Kapolei, HI

    Pool Hot Tub

    $455 to $1,500/night

  81. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,500/night

  82. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Pool Hot Tub

    $559 to $1,784/night

  83. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  84. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Pool Hot Tub

    $508 to $1,784/night

  85. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  86. 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

  87. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,016/night

  88. CONDOMINIUM
    Hale Lanikai Ko Olina Beach Villa (O1104)

    Hale Lanikai Ko Olina Beach Villa (O1104)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,384/night

  89. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  90. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Pool Hot Tub

    $478 to $1,384/night

  91. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  92. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $356 to $686/night

  93. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Pool Hot Tub

    $397 to $1,204/night

  94. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  95. 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

  96. 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

  97. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Pool Hot Tub

    $408 to $1,268/night

  98. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Kapolei, HI

    Pool Hot Tub

    $571 to $2,016/night

  99. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  100. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Pool Hot Tub

    $286 to $478/night