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. $215 to $331/night

    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  2. $209 to $354/night

    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  3. $232 to $406/night

    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  4. $191 to $331/night

    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  5. $284 to $706/night

    Kaanapali Shores #916

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $336 to $706/night

    Kaanapali Shores #825

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $296 to $447/night

    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $625 to $1,648/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
  9. $232 to $331/night

    Maui Kaanapali Villas #B231

    Maui Kaanapali Villas #B231

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $319 to $510/night

    Maui Kaanapali Villas #D275

    Maui Kaanapali Villas #D275

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  11. $1,900 to $2,969/night

    Makena Aloha Estate

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  12. $186 to $365/night

    Maui Kaanapali Villas #A116

    Maui Kaanapali Villas #A116

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $191 to $365/night

    Maui Kaanapali Villas #A517

    Maui Kaanapali Villas #A517

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  14. $348 to $800/night

    Kaanapali Shores #255

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $203 to $348/night

    Maui Kaanapali Villas #A317

    Maui Kaanapali Villas #A317

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. $220 to $418/night

    Maui Kaanapali Villas #E290

    Maui Kaanapali Villas #E290

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  17. $220 to $377/night

    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $208 to $338/night

    Papakea J103

    Papakea J103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  19. $429 to $800/night

    Kaanapali Shores #160

    Kaanapali Shores #160

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. $226 to $344/night

    Papakea A309

    Papakea A309

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  21. $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
  22. $257 to $306/night

    Plantation at Princeville 1322

    Plantation at Princeville 1322

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $339 to $1,056/night

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $424 to $1,125/night

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $481 to $1,167/night

    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    2 Bedrooms2.25 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $194 to $279/night

    Sea Village 1-205-Oceanfront

    Sea Village 1-205-Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  27. $264 to $299/night

    Hula Hideaway-303

    Hula Hideaway-303

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. $229 to $365/night

    Honua Kai Konea 224

    Honua Kai Konea 224

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $197 to $354/night

    Maui Kaanapali Villas #C160

    Maui Kaanapali Villas #C160

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  30. $325 to $549/night

    Maui Kaanapali Villas #D271

    Maui Kaanapali Villas #D271

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $209 to $383/night

    Maui Kaanapali Villas #A221

    Maui Kaanapali Villas #A221

    Studio BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $858 to $2,575/night

    Honua Kai-Konea #925

    Honua Kai-Konea #925

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  33. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  34. $487 to $1,183/night

    Sands of Kahana #292

    Sands of Kahana #292

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  35. $325 to $667/night

    Honua Kai-Konea #537

    Honua Kai-Konea #537

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. $493 to $1,467/night

    Honua Kai-Konea #539

    Honua Kai-Konea #539

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  37. $194 to $563/night

    Fairway Villas M2 at the Waikoloa Beach Resort

    Fairway Villas M2 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. $241 to $704/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
  39. $464 to $1,351/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