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. $284 to $747/night

    Hale Ono Loa 120

    Hale Ono Loa 120

    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. $250 to $741/night

    Pohailani 231

    Pohailani 231

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  5. $309 to $438/night

    Diamond Head Beach Hotel 801

    Diamond Head Beach Hotel 801

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  6. $216 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $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
  9. $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
  10. $194 to $649/night

    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $186 to $336/night

    Villas of Kamalii 37

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $148 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $192 to $238/night

    Kamahana 24

    Kamahana 24

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  14. $215 to $257/night

    Sealodge F9

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    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. $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
  17. $353 to $443/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  18. $178 to $319/night

    Hale Ono Loa #316

    Hale Ono Loa #316

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  19. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  20. $227 to $280/night

    Sealodge G8

    Sealodge G8

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  21. $1,392 to $1,906/night

    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
  22. $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
  23. $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
  24. $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
  25. $198 to $257/night

    Sealodge J2

    Sealodge J2

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  26. $427 to $594/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  27. $217 to $604/night

    Aina Nalu Premier Condo I207

    Aina Nalu Premier Condo I207

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  28. $327 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $371 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $181 to $636/night

    Napili Shores F147

    Napili Shores F147

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  31. $231 to $275/night

    Sealodge D1

    Sealodge D1

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  32. $279 to $401/night

    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  33. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  34. $625 to $1,650/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $128 to $601/night

    THE SHORES OF MAUI #223

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $155 to $451/night

    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $112 to $156/night

    Sandpiper 121B

    Sandpiper 121B

    Studio BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $688 to $1,464/night

    Pu'uwai Hale

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  39. $1,008 to $1,404/night

    Makalae

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  40. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  41. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $245 to $363/night

    Poipu Kapili 46

    Poipu Kapili 46

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  43. $201 to $274/night

    Hoyochi Nikko #109

    Hoyochi Nikko #109

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  44. $117 to $243/night

    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $264 to $271/night

    New Listing! Hawaiian Experience- Walk to Two Step

    New Listing! Hawaiian Experience- Walk to Two Step

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  46. $281 to $394/night

    Regency at Poipu Kai #914

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  47. $209 to $269/night

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    Lower Honoapiilani Condo 1 Bedroom Sleeps 4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  49. $247 to $291/night

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    Lower Honoapiilani Condo 2 Bedrooms Sleeps 4

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  50. $258 to $776/night

    Kahana Villa E614

    Kahana Villa E614

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  51. $274 to $776/night

    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $311 to $428/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  53. $361 to $479/night

    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    4 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  54. $227 to $275/night

    Sealodge E10

    Sealodge E10

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  55. $175 to $288/night

    Sea Village #4206

    Sea Village #4206

    1 Bedroom BathroomSleeps 3
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. $464 to $1,354/night

    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $164 to $480/night

    Beach Villas M3

    Beach Villas M3

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $241 to $705/night

    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $156 to $429/night

    Sea Village #1303

    Sea Village #1303

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $271 to $790/night

    Palm Villa I3 at the Mauna Lani Resort

    Palm Villa I3 at the Mauna Lani Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  61. $176 to $538/night

    Kona Reef #A33

    Kona Reef #A33

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  63. $172 to $369/night

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. $240 to $308/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  65. $198 to $238/night

    Puamana 9C

    Puamana 9C

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  66. $234 to $464/night

    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  67. $146 to $183/night

    Kona Pacific

    Kona Pacific

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. $164 to $231/night

    Sea Village 1-203

    Sea Village 1-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  69. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  70. $220 to $448/night

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  71. $240 to $338/night

    Plantations at Princeville #521

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub