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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $188 to $499/night

  2. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $163 to $435/night

  3. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $338/night

  4. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  5. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  6. 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

  7. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $183 to $407/night

  8. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $501/night

  9. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  10. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  11. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  12. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $437/night

  13. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  14. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $464/night

  15. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $498/night

  16. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525/night

  17. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $536/night

  18. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $464/night

  19. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $154 to $381/night

  20. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Pool
    FREE CANCELLATION

    $124 to $476/night

  21. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $150 to $464/night

  22. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525 to $642/night

  23. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $471/night

  24. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $411/night

  25. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,323 to $1,324/night

  26. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $467 to $773/night

  27. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,138 to $1,535/night

  28. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $445/night

  29. HOUSE
    Pineapple Hale

    Pineapple Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,928/night