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. CONDOMINIUM
    Wailea Grand Champion, #148

    Wailea Grand Champion, #148

    Wailea, HI

    Pool Hot Tub

    $223 to $549/night

  2. CONDOMINIUM
    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    Wailea, HI

    Pool

    $448 to $896/night

  3. CONDOMINIUM
    Mahana Resort #1017

    Mahana Resort #1017

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $290 to $606/night

  4. HOUSE
    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $341/night

  5. CONDOMINIUM
    Papakea #H103

    Papakea #H103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $580/night

  6. HOUSE
    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  7. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  8. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  9. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  10. CONDOMINIUM
    Kamaole Sands #2-306

    Kamaole Sands #2-306

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $347/night

  11. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  12. CONDOMINIUM
    209

    209

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  13. CONDOMINIUM
    131

    131

    Kihei, HI

    Pool
    FREE CANCELLATION

    $188 to $258/night

  14. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  15. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $210 to $495/night

  16. CONDOMINIUM
    Kamaole Sands #5-414

    Kamaole Sands #5-414

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $273 to $429/night

  17. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $202 to $484/night

  18. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $774/night

  19. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $416/night

  20. CONDOMINIUM
    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $331/night

  21. CONDOMINIUM
    Hale Mahina #B103

    Hale Mahina #B103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $478/night

  22. CONDOMINIUM
    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $209 to $354/night

  23. CONDOMINIUM
    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $331/night

  24. CONDOMINIUM
    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $296 to $447/night

  25. CONDOMINIUM
    Kaanapali Shores #916

    Kaanapali Shores #916

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $284 to $706/night

  26. CONDOMINIUM
    Papakea #A105

    Papakea #A105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $459/night

  27. CONDOMINIUM
    Kaanapali Royal #A303

    Kaanapali Royal #A303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $278 to $600/night

  28. CONDOMINIUM
    Valley Isle #1209

    Valley Isle #1209

    Lahaina, HI

    FREE CANCELLATION

    $232 to $669/night

  29. CONDOMINIUM
    Royal Kahana #319

    Royal Kahana #319

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $122 to $406/night

  30. CONDOMINIUM
    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $406/night