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. $235 to $367/night

    Puako Beach Condo 109

    Puako Beach Condo 109

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  2. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  3. $631 to $1,534/night

    Milo Hae Hale

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  4. $599 to $1,458/night

    Piko Nani

    Piko Nani

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  5. $1,137 to $2,654/night

    Ke Kailani Hale A2

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  6. $542 to $780/night

    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  7. $750 to $1,616/night

    Hokulani Villa

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  8. $845 to $2,366/night

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

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  9. $1,137 to $2,029/night

    Ali'i Villa

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  10. $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
  11. $296 to $409/night

    Noelani #110

    Noelani #110

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $291 to $419/night

    Maui Kai 602

    Maui Kai 602

    Studio BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $249 to $346/night

    Kaanapali Shores 836

    Kaanapali Shores 836

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $259 to $394/night

    Kapalua Golf Villas 16T1

    Kapalua Golf Villas 16T1

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $425 to $729/night

    Happy Leilani Hale

    Happy Leilani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $219 to $624/night

    Kaanapali Shores 819

    Kaanapali Shores 819

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $278 to $400/night

    Kaanapali Shores 942

    Kaanapali Shores 942

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $1,900 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  19. $1,318 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  20. $219 to $334/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $278 to $400/night

    Kaanapali Shores 941

    Kaanapali Shores 941

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $1,266 to $3,944/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  23. $326 to $714/night

    Hale Oliveira

    Hale Oliveira

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  24. $263 to $380/night

    Papakea J107

    Papakea J107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $2,203 to $4,290/night

    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  26. $256 to $345/night

    Kaanapali Shores 936

    Kaanapali Shores 936

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $375 to $789/night

    Ilikai 1243

    Ilikai 1243

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $2,000 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $300 to $315/night

    Maui Banyan Q306

    Maui Banyan Q306

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $208 to $269/night

    Kamaole Sands 8-203

    Kamaole Sands 8-203

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $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
  32. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  33. $664 to $1,673/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  34. $208 to $250/night

    Hale Kamaole 109

    Hale Kamaole 109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $576 to $883/night

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $1,109/night

    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $542 to $555/night

    Hale Pahukoa

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  39. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. $306 to $419/night

    Kona Bay View House

    Kona Bay View House

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  41. $710 to $1,875/night

    Pineapple Hale

    Pineapple Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. $506 to $899/night

    Holua Kai #34

    Holua Kai #34

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  43. $584 to $1,598/night

    Honu O Kai (Turtle of the Sea)

    Honu O Kai (Turtle of the Sea)

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  44. $214 to $319/night

    Kihei Akahi C-616

    Kihei Akahi C-616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  46. $220 to $356/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  47. $259 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. $208 to $310/night

    Island Surf 409

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  49. $278 to $400/night

    Papakea B201

    Papakea B201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. $899 to $1,434/night

    Hale Kauka

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  51. $417 to $756/night

    Hilo Shangrila

    Hilo Shangrila

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  52. $1,373 to $3,444/night

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18)

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    4 Bedrooms4.5 BathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
  53. $1,315 to $2,930/night

    O'oma Plantation

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  54. $245 to $374/night

    Kahana Reef 201

    Kahana Reef 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $1,553 to $3,338/night

    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  56. $744 to $2,192/night

    Blue Hawaii

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  57. $329 to $490/night

    Island Sands 210

    Island Sands 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $307 to $491/night

    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $306 to $556/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $304 to $366/night

    Eldorado A203

    Eldorado A203

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $200 to $316/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $251 to $384/night

    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  63. $200 to $299/night

    Kihei Alii Kai A207

    Kihei Alii Kai A207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $1,162 to $1,175/night

    Hale Lani

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  65. $877 to $1,395/night

    Kona Bubbles

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  66. $535 to $1,250/night

    Keauhou Estates #189

    Keauhou Estates #189

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $599 to $1,386/night

    Hale Aikane

    Hale Aikane

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  68. $601 to $1,317/night

    Leilani Kai Hale

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  69. $589 to $1,325/night

    Ho'o Maluhia

    Ho'o Maluhia

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  70. $482 to $720/night

    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  71. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  72. $1,434 to $3,932/night

    Mermaid Cove

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  73. $230 to $445/night

    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. $512 to $957/night

    Ono Oasis

    Ono Oasis

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  75. $240 to $339/night

    Kihei Alii Kai A101

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $274 to $465/night

    Nohonani 405

    Nohonani 405

    2 Bedrooms1.5  BathroomSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  77. $240/night

    Keauhou Elima

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool
  78. $766 to $2,122/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  79. $233 to $344/night

    Kahana Manor 410

    Kahana Manor 410

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. $1,328 to $3,627/night

    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  81. $210 to $363/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. $1,797 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  83. $194 to $249/night

    Kauhale Makai 529

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. $313 to $421/night

    Kihei Kai Nani 373

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $482 to $839/night

    Kahakai Estates Hale

    Kahakai Estates Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  86. $1,858 to $5,441/night

    Hale Pua

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  87. $549/night

    Ono Hale

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  88. $200 to $299/night

    Kamaole Sands 5-313

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION