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. $178 to $248/night

    Diamond Head Beach Hotel 1002

    Diamond Head Beach Hotel 1002

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  2. $178 to $285/night

    Hale Ono Loa #316

    Hale Ono Loa #316

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

    Kauai Tree House

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  5. $126 to $231/night

    Kihei Akahi #DG06

    Kihei Akahi #DG06

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  6. $421 to $448/night

    Kona Makai 3-302

    Kona Makai 3-302

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $267 to $418/night

    Luana Kai #A-103

    Luana Kai #A-103

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  8. $177 to $348/night

    Luana Kai #C-203

    Luana Kai #C-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  9. $239 to $389/night

    Maui Kamaole #B-206

    Maui Kamaole #B-206

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $203 to $264/night

    Nani Kai Hale # 308

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  11. $375 to $459/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  12. $289 to $493/night

    Palms at Wailea #1101

    Palms at Wailea #1101

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $347 to $521/night

    Palms at Wailea #1105

    Palms at Wailea #1105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $293 to $479/night

    Palms at Wailea #603

    Palms at Wailea #603

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $159 to $182/night

    Sandpiper 120A

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $226 to $257/night

    Sealodge G4

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  17. $329/night

    Turtle Bay Hanalei***TA-147868876801

    Turtle Bay Hanalei***TA-147868876801

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $306/night

    Turtle Bay Haupia**TA-136982118401

    Turtle Bay Haupia**TA-136982118401

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $641 to $934/night

    Turtle Rock

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  20. $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
  21. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $320 to $703/night

    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    3 BedroomsBathroomsSleeps 7
    4 nights minstay
    Pool
    FREE CANCELLATION
  24. $345 to $558/night

    Wailea Ekolu #105

    Wailea Ekolu #105

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  25. $261 to $347/night

    Wailea Ekolu #407

    Wailea Ekolu #407

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  26. $261 to $521/night

    Wailea Ekolu #501

    Wailea Ekolu #501

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  27. $261 to $405/night

    Wailea Ekolu #804

    Wailea Ekolu #804

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. $322 to $430/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  29. $456 to $609/night

    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub