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. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  4. HOUSE
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  5. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  6. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  7. HOUSE
    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  8. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  9. CONDOMINIUM
    1BR w/ Ocean View Lanai & Pool

    1BR w/ Ocean View Lanai & Pool

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $118 to $267/night

  10. CONDOMINIUM
    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    Kihei, HI

    Pool
    FREE CANCELLATION

    $117 to $414/night

  11. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  12. 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

  13. CONDOMINIUM
    2BR Beachfront Condo w/ Ocean View

    2BR Beachfront Condo w/ Ocean View

    Kihei, HI

    Pool
    FREE CANCELLATION

    $320 to $799/night

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

    2BR Garden Cottage- Walk to Beach!

    Honolulu, HI

    FREE CANCELLATION

    $139 to $454/night

  15. DUPLEX
    2BR w/ Diamond Head Views & Lanai

    2BR w/ Diamond Head Views & Lanai

    Honolulu, HI

    Pets OK
    FREE CANCELLATION

    $258 to $646/night

  16. 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

  17. CONDOMINIUM
    328

    328

    Kihei, HI

    Pool
    FREE CANCELLATION

    $258 to $409/night

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

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $1,082 to $3,365/night

  19. 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

  20. 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

  21. 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

  22. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,182 to $3,546/night

  23. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  24. 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

  25. 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

  26. 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

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

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,166 to $3,653/night

  28. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

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

    7 C's Kona (Big Island)

    Kailua Kona, HI

    Pool

    $482 to $720/night

  30. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $371/night

  31. CONDOMINIUM
    Aina Nalu A104

    Aina Nalu A104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $250 to $499/night

  32. CONDOMINIUM
    Aina Nalu B106- Extremely Rare Unit

    Aina Nalu B106- Extremely Rare Unit

    Lahaina, HI

    Pool Hot Tub

    $262 to $737/night

  33. CONDOMINIUM
    Aina Nalu B204

    Aina Nalu B204

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $577/night

  34. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $181 to $371/night

  35. CONDOMINIUM
    Aina Nalu C102

    Aina Nalu C102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $623/night

  36. CONDOMINIUM
    Aina Nalu C108

    Aina Nalu C108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $623/night

  37. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $475/night

  38. 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

  39. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $446/night

  40. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $239/night

  41. CONDOMINIUM
    Aina Nalu K102

    Aina Nalu K102

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $449/night

  42. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    FREE CANCELLATION

    $481 to $896/night

  43. CONDOMINIUM
    Ali'i Kai 4202

    Ali'i Kai 4202

    Princeville, HI

    Pool
    FREE CANCELLATION

    $234 to $799/night

  44. CONDOMINIUM
    Ali'i Kai 4303

    Ali'i Kai 4303

    Princeville, HI

    Pool
    FREE CANCELLATION

    $120 to $799/night

  45. CONDOMINIUM
    Ali'i Kai 7204

    Ali'i Kai 7204

    Princeville, HI

    Pool
    FREE CANCELLATION

    $125 to $842/night

  46. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Pool Hot Tub

    $1,137 to $2,029/night

  47. CONDOMINIUM
    Alii Kai 3103

    Alii Kai 3103

    Princeville, HI

    Pool
    FREE CANCELLATION

    $238 to $293/night

  48. CONDOMINIUM
    Alii Kai 5301

    Alii Kai 5301

    Princeville, HI

    Pool
    FREE CANCELLATION

    $275 to $306/night

  49. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  50. CONDOMINIUM
    Alii Villas C-125

    Alii Villas C-125

    Kailua Kona, HI

    Pool

    $238 to $490/night

  51. CONDOMINIUM
    Aloha Surf 1507 Condominium

    Aloha Surf 1507 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $106 to $158/night

  52. CONDOMINIUM
    Aloha Surf 1509

    Aloha Surf 1509

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $111 to $180/night

  53. CONDOMINIUM
    Aloha Surf 207

    Aloha Surf 207

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $99 to $129/night

  54. HOTEL ROOM
    Aloha Surf 315 Hotel Suites

    Aloha Surf 315 Hotel Suites

    Honolulu, HI

    Pool
    FREE CANCELLATION
  55. CONDOMINIUM
    Aloha Surf 504 *LEGAL VACATION RENTAL

    Aloha Surf 504 *LEGAL VACATION RENTAL

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $96 to $224/night

  56. HOTEL ROOM
    Aloha Surf 601 Hotel Suites

    Aloha Surf 601 Hotel Suites

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $119 to $164/night

  57. APARTMENT
    Aloha Surf 610 Apartment

    Aloha Surf 610 Apartment

    Honolulu, HI

    Pool
    FREE CANCELLATION
  58. APARTMENT
    AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH

    AS1205 444 Kanekapolei St Honolulu TH-PTO-00-ACH

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $113 to $161/night

  59. CONDOMINIUM
    AV 302

    AV 302

    Kailua Kona, HI

    Pool

    $102 to $162/night

  60. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  61. CONDOMINIUM
    Bali Hai Villas 1 Bedroom

    Bali Hai Villas 1 Bedroom

    Princeville, HI

    Pool Hot Tub
  62. CONDOMINIUM
    Bali Hai Villas 2 Bedroom

    Bali Hai Villas 2 Bedroom

    Princeville, HI

    Pool Hot Tub
  63. CONDOMINIUM
    Bali Hai Villas 3 Bedroom

    Bali Hai Villas 3 Bedroom

    Princeville, HI

    Pool Hot Tub
  64. CONDOMINIUM
    Bamboo #408

    Bamboo #408

    Waikiki, HI

    Pool Hot Tub

    $106 to $140/night

  65. CONDOMINIUM
    Bamboo 1001 Condominium

    Bamboo 1001 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $142 to $197/night

  66. APARTMENT
    Bamboo 301 Apartment

    Bamboo 301 Apartment

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $144 to $208/night

  67. CONDOMINIUM
    Bamboo 308 Condominium

    Bamboo 308 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $122 to $186/night

  68. CONDOMINIUM
    Bamboo 405 Condominium

    Bamboo 405 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION
  69. CONDOMINIUM
    Bamboo 505 Condominium

    Bamboo 505 Condominium

    Honolulu, HI

    FREE CANCELLATION
  70. CONDOMINIUM
    Bamboo 601 Condominium

    Bamboo 601 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION
  71. APARTMENT
    Bamboo 610 Studio Apartment

    Bamboo 610 Studio Apartment

    Honolulu, HI

    Pool Hot Tub
    FREE CANCELLATION
  72. CONDOMINIUM
    Bamboo 702 Condominium

    Bamboo 702 Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION
  73. CONDOMINIUM
    Bamboo 801 Condominium

    Bamboo 801 Condominium

    Honolulu, HI

    FREE CANCELLATION
  74. HOTEL ROOM
    Bamboo 902 Hotel Suites

    Bamboo 902 Hotel Suites

    Honolulu, HI

    Pool
    FREE CANCELLATION
  75. CONDOMINIUM
    Bamboo 906 Condominium

    Bamboo 906 Condominium

    Honolulu, HI

    FREE CANCELLATION
  76. CONDOMINIUM
    Banyan 1608-I Condominium

    Banyan 1608-I Condominium

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $152 to $248/night

  77. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  78. CONDOMINIUM
    Bay Villa 33B2

    Bay Villa 33B2

    Lahaina, HI

    Pool

    $214 to $270/night

  79. CONDOMINIUM
    Bay Villa 37G4

    Bay Villa 37G4

    Lahaina, HI

    Pool

    $366 to $501/night

  80. CONDOMINIUM
    Bay Villa 38G2

    Bay Villa 38G2

    Lahaina, HI

    Pool

    $248 to $304/night

  81. CONDOMINIUM
    Bay Villa 38G3

    Bay Villa 38G3

    Lahaina, HI

    Pool

    $248 to $304/night

  82. 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

  83. CONDOMINIUM
    Beach Villas at Kahalu'u 2-101

    Beach Villas at Kahalu'u 2-101

    Kailua Kona, HI

    Pool

    $304 to $647/night

  84. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  85. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Pool

    $744 to $2,568/night

  86. HOUSE
    Blue Kehena

    Blue Kehena

    Pahoa, HI

    $279 to $521/night

  87. APARTMENT
    Cabana 301 Apartment

    Cabana 301 Apartment

    Honolulu, HI

    FREE CANCELLATION

    $129 to $180/night

  88. APARTMENT
    Cabana 401 Apartment

    Cabana 401 Apartment

    Honolulu, HI

    FREE CANCELLATION
  89. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  90. CONDOMINIUM
    Casa de Emdeko 337

    Casa de Emdeko 337

    Kailua-Kona, HI

    Pool

    $140 to $228/night

  91. HOUSE
    Chung Cottage

    Chung Cottage

    Hanalei, HI

    FREE CANCELLATION

    $249 to $312/night

  92. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  93. 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

  94. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  95. CONDOMINIUM
    D1-2 Bedroom Beachfront

    D1-2 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $416 to $664/night

  96. CONDOMINIUM
    Diamond Head Beach #805

    Diamond Head Beach #805

    Waikiki, HI

    $139 to $183/night

  97. CONDOMINIUM
    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    Honolulu, HI

    FREE CANCELLATION

    $178 to $248/night

  98. CONDOMINIUM
    Diamond Head Beach Hotel 1005

    Diamond Head Beach Hotel 1005

    Honolulu, HI

    FREE CANCELLATION

    $144 to $186/night

  99. APARTMENT
    Diamond Head Beach Hotel 1104

    Diamond Head Beach Hotel 1104

    Honolulu, HI

    FREE CANCELLATION

    $144 to $180/night

  100. APARTMENT
    Diamond Head Beach Hotel 1105

    Diamond Head Beach Hotel 1105

    Honolulu, HI

    FREE CANCELLATION

    $160 to $197/night