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. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  2. $359 to $1,096/night

    Kona Makai 6301

    Kona Makai 6301

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  3. $372 to $444/night

    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $372 to $444/night

    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $1,869 to $3,125/night

    Papaua Paradise 43

    Papaua Paradise 43

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  6. $278 to $341/night

    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $188 to $724/night

    Maui Kai 506

    Maui Kai 506

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $513 to $988/night

    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $341 to $413/night

    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $218 to $383/night

    Kamaole Sands #10-205

    Kamaole Sands #10-205

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  11. $173 to $365/night

    Kamaole Sands #7-304

    Kamaole Sands #7-304

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $255 to $675/night

    Maui Kai 201

    Maui Kai 201

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $278 to $341/night

    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $258 to $341/night

    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $261 to $455/night

    Kamaole Sands #3-402

    Kamaole Sands #3-402

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $160 to $345/night

    Royal Kahana 106

    Royal Kahana 106

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $133 to $360/night

    Kamaole Sands #5-103

    Kamaole Sands #5-103

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $173 to $411/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $251 to $442/night

    Kamaole Sands #1-406

    Kamaole Sands #1-406

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $244 to $558/night

    Holualoa Bay Villas 102

    Holualoa Bay Villas 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  21. $372 to $444/night

    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $258 to $309/night

    Junior Suite Oceanfront #707

    Junior Suite Oceanfront #707

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $341 to $413/night

    1 Bedroom Oceanfront #604

    1 Bedroom Oceanfront #604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $370 to $1,139/night

    Kona Makai 6201

    Kona Makai 6201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  25. $249 to $429/night

    Kamaole Sands #6-408

    Kamaole Sands #6-408

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. $196 to $273/night

    Kamaole Sands #9-207

    Kamaole Sands #9-207

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  27. $278 to $341/night

    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $225 to $443/night

    Royal Kahana 920

    Royal Kahana 920

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  29. $216 to $348/night

    Kamaole Sands #10-312

    Kamaole Sands #10-312

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $278 to $341/night

    Junior Suite Oceanfront #702

    Junior Suite Oceanfront #702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $278 to $341/night

    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $278 to $341/night

    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $278 to $341/night

    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. $194 to $346/night

    Kamaole Sands #10-111

    Kamaole Sands #10-111

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  35. $278 to $341/night

    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $157 to $289/night

    Kamaole Sands #8-310

    Kamaole Sands #8-310

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $681 to $1,717/night

    Wailea Elua #2303

    Wailea Elua #2303

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $160 to $304/night

    Royal Kahana 202

    Royal Kahana 202

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION