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. $175 to $183/night

    Villas on the Prince 34

    Villas on the Prince 34

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $322 to $430/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  3. $347 to $521/night

    Palms at Wailea #1105

    Palms at Wailea #1105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $300 to $358/night

    Hale Kamaole #201

    Hale Kamaole #201

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  5. $656 to $875/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  6. $293 to $477/night

    Palms at Wailea #603

    Palms at Wailea #603

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $319 to $447/night

    Maui Kamaole #A-202

    Maui Kamaole #A-202

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $196 to $273/night

    Kamaole Sands #9-207

    Kamaole Sands #9-207

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $346 to $552/night

    Wailea Ekolu #105

    Wailea Ekolu #105

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  10. $126 to $231/night

    Kihei Bay Vista #C-106

    Kihei Bay Vista #C-106

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $261 to $521/night

    Wailea Ekolu #501

    Wailea Ekolu #501

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  12. $302 to $458/night

    Maui Kamaole #A-203

    Maui Kamaole #A-203

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $274 to $442/night

    Kamaole Sands #7-408

    Kamaole Sands #7-408

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $215 to $325/night

    Grand Champions #86

    Grand Champions #86

    1 BedroomBathroomsSleeps 2
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $226 to $257/night

    Sealodge G4

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  16. $329/night

    Turtle Bay Hanalei***TA-147868876801

    Turtle Bay Hanalei***TA-147868876801

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $258 to $393/night

    309

    309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  18. $456 to $609/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  19. $375 to $459/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  20. $178 to $375/night

    Hale Ono Loa #316

    Hale Ono Loa #316

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  21. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $421 to $444/night

    Kona Makai 3-302

    Kona Makai 3-302

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $157 to $261/night

    Keawakapu Views #206

    Keawakapu Views #206

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  25. $289 to $493/night

    Palms at Wailea #1101

    Palms at Wailea #1101

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $157 to $277/night

    Waiohuli Beach Hale #D-122

    Waiohuli Beach Hale #D-122

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  27. $150 to $242/night

    Kihei Akahi #C-217

    Kihei Akahi #C-217

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. $264 to $430/night

    Grand Champions #48

    Grand Champions #48

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $157 to $277/night

    Waiohuli Beach Hale #D-221

    Waiohuli Beach Hale #D-221

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. $157 to $277/night

    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  31. $347 to $695/night

    Maui Hill #I-99

    Maui Hill #I-99

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $204 to $413/night

    Maui Kamaole #K-108

    Maui Kamaole #K-108

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $157 to $277/night

    Waiohuli Beach Hale #B-108

    Waiohuli Beach Hale #B-108

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $202 to $289/night

    Maui Vista #2-418

    Maui Vista #2-418

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  35. $261 to $347/night

    Wailea Ekolu #407

    Wailea Ekolu #407

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  36. $231 to $377/night

    Maui Kamaole #I-215

    Maui Kamaole #I-215

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $307 to $522/night

    Wailea Ekolu #205

    Wailea Ekolu #205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. $324 to $486/night

    Maui Kamaole #J-219

    Maui Kamaole #J-219

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $239 to $387/night

    Maui Kamaole #B-206

    Maui Kamaole #B-206

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. $302 to $418/night

    Maui Kamaole #F-207

    Maui Kamaole #F-207

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $174 to $347/night

    Maui Kamaole #I-109

    Maui Kamaole #I-109

    1 BedroomBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. $159 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  43. $178 to $248/night

    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  44. $306/night

    Turtle Bay Haupia**TA-136982118401

    Turtle Bay Haupia**TA-136982118401

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  46. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  47. $320 to $703/night

    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    3 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  48. $188 to $258/night

    131

    131

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  49. $334 to $398/night

    Kauai Tree House

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  50. $813 to $1,219/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  51. $261 to $405/night

    Wailea Ekolu #804

    Wailea Ekolu #804

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  52. $208 to $347/night

    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  53. $405 to $579/night

    Palms at Wailea #1507

    Palms at Wailea #1507

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. $126 to $231/night

    Kihei Akahi #DG06

    Kihei Akahi #DG06

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  55. $157 to $277/night

    Waiohuli Beach Hale #D-120

    Waiohuli Beach Hale #D-120

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
    FREE CANCELLATION
  56. $191 to $347/night

    Maui Kamaole #J-120

    Maui Kamaole #J-120

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  57. $138 to $231/night

    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. $239 to $390/night

    Maui Kamaole #G-101

    Maui Kamaole #G-101

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  59. $177 to $345/night

    Luana Kai #C-203

    Luana Kai #C-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. $255 to $473/night

    Maui Vista #2-423

    Maui Vista #2-423

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  61. $267 to $418/night

    Luana Kai #A-103

    Luana Kai #A-103

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION