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. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool

    $689 to $1,678/night

  2. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Pool Hot Tub

    $1,518 to $2,364/night

  3. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525/night

  4. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $403/night

  5. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $166 to $498/night

  6. HOUSE
    Ho'o Maluhia

    Ho'o Maluhia

    Kailua Kona, HI

    Pool

    $444 to $730/night

  7. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  8. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,917 to $5,992/night

  9. CONDOMINIUM
    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $384/night

  10. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Pool

    $876 to $1,284/night

  11. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $538/night

  12. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $813/night

  13. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $466/night

  14. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $466/night

  15. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  16. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Pool

    $555 to $759/night

  17. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759/night

  18. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $353/night

  19. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  20. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $486 to $608/night

  21. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $466/night

  22. HOUSE
    Kahalu'u Hale

    Kahalu'u Hale

    Kailua Kona, HI

    Pool

    $350 to $467/night

  23. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  24. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  25. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $146 to $360/night

  26. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $499/night

  27. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  28. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $565 to $826/night

  29. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $623/night

  30. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $138 to $501/night