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. $202 to $636/night

    Lahaina Condo K202

    Lahaina Condo K202

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  2. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $322 to $435/night

    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  4. $231 to $618/night

    Lahaina Condo J209

    Lahaina Condo J209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  5. $250 to $741/night

    Pohailani 231

    Pohailani 231

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $309 to $438/night

    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  7. $217 to $623/night

    Aina Nalu C102

    Aina Nalu C102

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $202 to $636/night

    Aina Nalu Condo B103

    Aina Nalu Condo B103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  9. $202 to $636/night

    Aina Nalu Condo C208

    Aina Nalu Condo C208

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $217 to $623/night

    Aina Nalu C108

    Aina Nalu C108

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $202 to $636/night

    Aina Nalu Condo A209

    Aina Nalu Condo A209

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  12. $248 to $326/night

    Diamond Head Beach Hotel 1202

    Diamond Head Beach Hotel 1202

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  13. $110 to $219/night

    Waikiki Grand 719

    Waikiki Grand 719

    Studio BathroomSleeps 2
    1 night minstay
    Pool Pets OK
    FREE CANCELLATION
  14. $274 to $409/night

    Nohonani #105

    Nohonani #105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  15. $202 to $636/night

    Aina Nalu Condo K107

    Aina Nalu Condo K107

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  16. $364 to $608/night

    Palm Villas F4 at Mauna Lani Resort

    Palm Villas F4 at Mauna Lani Resort

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  17. $307 to $524/night

    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  18. $231 to $618/night

    Lahaina Condo D203

    Lahaina Condo D203

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  19. $256 to $361/night

    Hanalei Bay Villa 26

    Hanalei Bay Villa 26

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  20. $175 to $215/night

    Villas on the Prince 28

    Villas on the Prince 28

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
    FREE CANCELLATION
  21. $221 to $431/night

    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $102 to $162/night

    AV 302

    AV 302

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  23. $181 to $242/night

    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  24. $216 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $172 to $238/night

    Hanalei Bay Resort 5201

    Hanalei Bay Resort 5201

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $286 to $478/night

    Hale Ohana Aloha

    Hale Ohana Aloha

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  27. $247 to $326/night

    Pali Ke Kua #241

    Pali Ke Kua #241

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  28. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $124 to $353/night

    Kona Magic Sands #111

    Kona Magic Sands #111

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $213 to $636/night

    Banyan Tree #305

    Banyan Tree #305

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  31. $399 to $1,125/night

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $138 to $480/night

    Sea Village #4202

    Sea Village #4202

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $179 to $521/night

    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $161 to $509/night

    Surf & Racquet Club #6-303

    Surf & Racquet Club #6-303

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $195 to $594/night

    Surf & Racquet Club #3-201

    Surf & Racquet Club #3-201

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $150 to $453/night

    Kona Makai #6302

    Kona Makai #6302

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $135 to $366/night

    Keauhou Resort #118

    Keauhou Resort #118

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  38. $250 to $536/night

    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $194 to $649/night

    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $4,194 to $7,190/night

    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  41. $186 to $336/night

    Villas of Kamalii 37

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $216 to $306/night

    Plantation at Princeville 1322

    Plantation at Princeville 1322

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $148 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $178 to $238/night

    Puamana 25B

    Puamana 25B

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  45. $345 to $458/night

    Puu Poa 405

    Puu Poa 405

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. $259 to $428/night

    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  47. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. $563 to $1,031/night

    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  49. $194 to $407/night

    Waikoloa Beach Villas P32

    Waikoloa Beach Villas P32

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $99 to $299/night

    1BR w/ Pools, Steps to Kamaole Beach 3

    1BR w/ Pools, Steps to Kamaole Beach 3

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  51. $259 to $428/night

    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  52. $364 to $729/night

    Hale Nui Ohana

    Hale Nui Ohana

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  53. $247 to $488/night

    Vista Waikoloa B-302

    Vista Waikoloa B-302

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $192 to $238/night

    Kamahana 24

    Kamahana 24

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  55. $217 to $604/night

    Aina Nalu Premier Condo G108

    Aina Nalu Premier Condo G108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $345/night

    Turtle Bay Sugar Cane***Available 30 day rental

    Turtle Bay Sugar Cane***Available 30 day rental

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. $191/night

    Turtle Bay Sea Shells**TA-154567065601 Available 30 nights

    Turtle Bay Sea Shells**TA-154567065601 Available 30 nigh...

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $271/night

    Turtle Bay Morning Glory***TA-147878707201 Available 30 nights

    Turtle Bay Morning Glory***TA-147878707201 Available 30 ...

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  60. $206 to $348/night

    Plantations at Princeville #111

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  61. $215 to $257/night

    Sealodge F9

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $425 to $729/night

    Happy Leilani Hale

    Happy Leilani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $194 to $431/night

    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $259 to $428/night

    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  65. $304 to $467/night

    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  66. $339 to $861/night

    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  67. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  68. $184 to $353/night

    Pohailani #133

    Pohailani #133

    2 Bedrooms BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  69. $203 to $553/night

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. $427 to $775/night

    Molokama

    Molokama

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  71. $481 to $896/night

    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  72. $190 to $623/night

    Aina Nalu Premier Condo B108

    Aina Nalu Premier Condo B108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  73. $204 to $238/night

    Cliffs 7303

    Cliffs 7303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $353 to $443/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  75. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  76. $178 to $319/night

    Hale Ono Loa #316

    Hale Ono Loa #316

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  77. $274 to $409/night

    Nohonani #300

    Nohonani #300

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. $228 to $353/night

    Noelani # 115

    Noelani # 115

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  79. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  80. $304 to $540/night

    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  81. $218 to $274/night

    Hoyochi Nikko #201

    Hoyochi Nikko #201

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  82. $227 to $280/night

    Sealodge G8

    Sealodge G8

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  83. $1,392 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  84. $296 to $521/night

    International Colony Club #18

    International Colony Club #18

    2 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  85. $274 to $409/night

    Nohonani #202

    Nohonani #202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  86. $178 to $487/night

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

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

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  87. $174 to $421/night

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. $146 to $286/night

    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  89. $278 to $572/night

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. $263 to $413/night

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    Mauna Lani All-Suite Getaway w/ Pools & Hot Tubs

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  91. $118 to $261/night

    Oceanfront Condo w/ Resort Amenities

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. $198 to $257/night

    Sealodge J2

    Sealodge J2

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  93. $377 to $591/night

    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $294 to $531/night

    Kapalua Bay Villa 15G5 Ocean View

    Kapalua Bay Villa 15G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
  95. $427 to $594/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  96. $178 to $263/night

    Alii Kai II 8H

    Alii Kai II 8H

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $416 to $664/night

    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  98. $304 to $467/night

    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  99. $305 to $448/night

    Waipouli Beach Resort C-205

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  100. $284 to $747/night

    Hale Ono Loa 120

    Hale Ono Loa 120

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION