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. TOWNHOUSE
    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $631/night

  2. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  3. CONDOMINIUM
    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $386 to $1,125/night

  4. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $1,060/night

  5. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  6. CONDOMINIUM
    Honua Kai-Konea #537

    Honua Kai-Konea #537

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $325 to $667/night

  7. CONDOMINIUM
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $493 to $1,467/night

  8. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,558/night

  9. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  10. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $429 to $800/night

  11. CONDOMINIUM
    Kaanapali Shores #255

    Kaanapali Shores #255

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $348 to $800/night

  12. CONDOMINIUM
    Kaanapali Shores #825

    Kaanapali Shores #825

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $336 to $706/night

  13. CONDOMINIUM
    Kaanapali Shores #916

    Kaanapali Shores #916

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $284 to $706/night

  14. CONDOMINIUM
    Kauai Beach Villas 2 Bedroom

    Kauai Beach Villas 2 Bedroom

    Lihue, HI

    Pool
  15. CONDOMINIUM
    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $625 to $1,655/night

  16. CONDOMINIUM
    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $438 to $1,356/night

  17. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  18. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $481 to $1,167/night

  19. CONDOMINIUM
    Maui Kaanapali Villas #A116

    Maui Kaanapali Villas #A116

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $365/night

  20. CONDOMINIUM
    Maui Kaanapali Villas #A221

    Maui Kaanapali Villas #A221

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $383/night

  21. CONDOMINIUM
    Maui Kaanapali Villas #A317

    Maui Kaanapali Villas #A317

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $348/night

  22. CONDOMINIUM
    Maui Kaanapali Villas #A517

    Maui Kaanapali Villas #A517

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $365/night

  23. CONDOMINIUM
    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $406/night

  24. CONDOMINIUM
    Maui Kaanapali Villas #B231

    Maui Kaanapali Villas #B231

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $331/night

  25. CONDOMINIUM
    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $447/night

  26. CONDOMINIUM
    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $331/night

  27. CONDOMINIUM
    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $331/night

  28. CONDOMINIUM
    Maui Kaanapali Villas #C160

    Maui Kaanapali Villas #C160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $197 to $354/night

  29. CONDOMINIUM
    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $209 to $354/night

  30. CONDOMINIUM
    Maui Kaanapali Villas #D271

    Maui Kaanapali Villas #D271

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $549/night

  31. CONDOMINIUM
    Maui Kaanapali Villas #D275

    Maui Kaanapali Villas #D275

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $510/night

  32. CONDOMINIUM
    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $377/night

  33. CONDOMINIUM
    Maui Kaanapali Villas #E290

    Maui Kaanapali Villas #E290

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $418/night

  34. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  35. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  36. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  37. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  38. CONDOMINIUM
    Sea Village 1-205-Oceanfront

    Sea Village 1-205-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $194 to $279/night

  39. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION