Hawaii Vacation Rentals - 1185 Properties

Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Over 300 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. Sleeps 6, $225 to $380/night

    City : Puako
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Step into this sunny and bright condo located directly across the...

  2. Sleeps 6, $475 to $535/night

    City : Kapaa
    Bedrooms : 2
    Bathrooms : 2

    Hale Hololani "Heavenly Home", Air Conditioned Kapa'a Beach Home...

  3. Sleeps 5, $330 to $395/night

    City : Kaanapali
    Bedroom : 1
    Bathroom : 1
    Pool

    One Bedroom- Flat screen TV; King bed, 2 Twins on lanai. (No Sofa...

  4. Sleeps 4, $160 to $335/night

    City : Lahaina
    Bedroom : 1
    Bathroom : 1
    Pool

    Oceanfront 1 bedroom unit with spacious kitchen and tile floors...

  5. Sleeps 10, $3425 to $5020/night

    City : Kailua-Kona
    Bedrooms : 3
    Bathrooms : 4
    Pool

    Perfectly located on the Kona “Gold Coast” of the Big Island...

  6. Sleeps 4, $150 to $175/night

    City : Princeville
    Bedroom : 1
    Bathrooms : 2
    Pool

    The Cliffs Resort at Princeville Unit 3201, Garden View North Shore...

  7. Sleeps 6, $390 to $485/night

    City : Koloa
    Bedrooms : 3
    Bathrooms : 3
    Pool

    This 3 Bedroom, 3 Bath Condo features Hawaiian style furniture and...

  8. Sleeps 4, $160 to $200/night

    City : Lihue
    Bedrooms : 2
    Bathroom : 1.5
    Pool

    Banyan Harbor Condos are centrally located, only 5 minutes from...

  9. Sleeps 10, $595 to $775/night

    City : Anahola
    Bedrooms : 4
    Bathrooms : 5
    Hot Tub

    Kauai Gardens Estate, Anahola, Kaua'i Vacation Rental. Private Kauai...

  10. Sleeps 6, $300 to $415/night

    City : Kapaa
    Bedrooms : 2
    Bathrooms : 3
    Pool

    Princeville is a 9,000-acre, upscale, unincorporated, master-planned...

  11. Sleeps 6, $1020 to $1255/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 2

    Brand new on the vacation rental market, this recently built home is...

  12. Sleeps 5, $345 to $575/night

    City : Puako
    Bedrooms : 3
    Bathroom : 1

    Discover the pleasure of an authentic Old Hawaii Puako Beach House...

  13. Sleeps 6, $225 to $290/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 2

    Tastefully designed by the Owner's to create a carefree island...

  14. Sleeps 6, $300 to $330/night

    City : Lihue
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Kaha Lani Unit #214, Ocean View, 2nd floor End Unit,   Walua,...

  15. Sleeps 4, $270 to $340/night

    City : Koloa
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Princeville is a 9,000-acre, upscale, unincorporated, master-planned...

  16. Sleeps 4, $230 to $255/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    A Million Dollar View! That’s what you get from the living room,...

  17. Sleeps 4, $165 to $190/night

    City : Princeville
    Bedroom : 1
    Bathrooms : 2
    Pool

    Ocean view, upgraded inside, with 1172 sq. ft. of living space,...

  18. Sleeps 5, $210 to $230/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Air Conditioned, spacious, beautifully decorated condo near beach...

  19. Sleeps 6, $180 to $190/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Enjoy your peaceful days and nights in this Beautiful and Tranquil...

  20. Sleeps 6, $250 to $275/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Pali Ke Kua, the cliffs of the gods, the most famous view in Kauai....

  21. Sleeps 6, $190 to $215/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Located ground floor at the edge of the Plantations at Princeville,...

  22. Sleeps 4, $230 to $255/night

    City : Koloa
    Bedroom : 1
    Bathrooms : 2
    Pool

    Located just a 4 minute walk away from the beautiful, family...

  23. Sleeps 2, $190 to $200/night

    City : Kapaa
    Bedroom : 1
    Bathroom : 1
    Pool

    Air Conditioned Beachfront Beautifully Remodeled Pono Kai the...

  24. Sleeps 6, $385 to $415/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Pu'u Poa 401- Romantic, air conditioned, totally private, luxury...

  25. Sleeps 3, $180 to $200/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1
    Pool

    Both sunrise and sunset views. Watch the whales play from your...

  26. Sleeps 3, $180 to $200/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1
    Pool

    Sealodge F9 is a top floor condo, 1br/1ba, private, with view of...

  27. Sleeps 5, $180 to $200/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    One of the best views in Sealodge. You are surrounded by ocean and...

  28. Sleeps 2, ~$210/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1
    Pool

    Sealodge G9 is a top floor condo with incredible views of both...

  29. Sleeps 6, $180 to $200/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This second floor end unit sits slightly back from the edge of the...

  30. Sleeps 5, $190 to $215/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1
    Pool

    Completely renovated in 2012, with all new stainless steel...