Hawaii Vacation Rentals - 2290 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, $405 to $455/night

    City : Kahana
    Bedrooms : 2
    Bathrooms : 2.5

    Kahana Sunset Unit F-1 is an ocean front 2-bedroom, 2 1/2 bath unit...

  2. Sleeps 6, $205 to $445/night

    City : Kailua-Kona
    Bedrooms : 2
    Bathrooms : 2.5

    Newly Remodeled!! This non-smoking well-appointed 2 bedroom unit is...

  3. Sleeps 6, $225 to $285/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 2

    Tastefully designed by the Owners to create a carefree island...

  4. Sleeps 6, $295 to $345/night

    City : kahana
    Bedrooms : 2
    Bathrooms : 2

    This newly remodeled unit has two flat screen TV's,VHS,DVD player,CD...

  5. Sleeps 8, $420 to $470/night

    City : Kahana
    Bedrooms : 3
    Bathrooms : 2

    The panoramic view of Molokai from this unit is spectacular. This...

  6. Sleeps 4, $145 to $200/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2

    Welcome to NKH 301, a wonderful 1 bedroom 2 full bath condo right on...

  7. Sleeps 5, $320 to $1015/night

    City : Waikoloa Village
    Bedrooms : 2
    Bathrooms : 2

    Welcome to our hand-picked collection of luxury vacation rental...

  8. Sleeps 5, $600 to $1240/night

    City : Mauna Lani
    Bedrooms : 2
    Bathrooms : 2.5

    Mauna Lani Terrace D203 is a beautiful luxury 2 bedroom / 2.5 bath,...

  9. Sleeps 4, $170 to $250/night

    City : Honolulu
    Bedrooms : 2
    Bathroom :

    This boutique Waikiki condo faces the Hilton Hawaiian Village, it is...

  10. Sleeps 4, $200 to $270/night

    City : Honolulu
    Bedrooms : 2
    Bathroom :

    This stunning 2 bedroom 2 bathroom condo is located in the One...

  11. Sleeps 4, $200 to $310/night

    City : Honolulu
    Bedroom : 1
    Bathroom : 1

    An affordable 1 bedroom suite in the Oceanfront Diamond Head Beach...

  12. Sleeps 4, $145 to $190/night

    City : Honolulu
    Bedroom : studio
    Bathroom : 1

    Located at the prestigious 2500 Kalakaua Avenue address, the...

  13. Sleeps 4, $125 to $200/night

    City : Honolulu
    Bedroom : 1
    Bathroom : 1

    Lavish yourself in the spirit of Old Hawaii, at the adorable...

  14. Sleeps 4, $270 to $310/night

    City : Honolulu
    Bedrooms : 2
    Bathrooms : 2

    Stunning sunsets and dramatic ocean views of Oahu’s renowned Gold...

  15. Sleeps 6, $280 to $320/night

    City : Kaneohe
    Bedrooms : 3
    Bathrooms : 3

    On the beautiful Windward Side of Oahu, time slows down. Gone are...

  16. Sleeps 4, $160 to $180/night

    City : Lihue
    Bedrooms : 2
    Bathroom : 1.5

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

  17. Sleeps 6, $260 to $415/night

    City : Kapaa
    Bedrooms : 2
    Bathrooms : 3

    First class Waipouli Beach Resort Location: Waipouli, East Kauai,...

  18. Sleeps 6, $175 to $205/night

    City : Kailua Kona
    Bedrooms : 2
    Bathrooms : 2

    Lovely Oceanfront upgraded second floor 2bd2bth unit in Kona Bali...

  19. Sleeps 6, $635 to $810/night

    City : Kailua-Kona
    Bedrooms : 3
    Bathrooms : 3.5

    Ali'i Point #5 is located at Ali'i Point, a private and gated...

  20. Sleeps 6, $175 to $185/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    Kamahana condos are spacious and private, with secluded yards and...

  21. Sleeps 6, $195 to $220/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    The Plantation at Princeville, located adjacent to the beautiful...

  22. Sleeps 2, $165 to $195/night

    City : Kapaa
    Bedroom : 1
    Bathroom : 1

    Air Conditioned Beachfront Beautifully Remodeled. Pono Kai the...

  23. Sleeps 5, $200 to $240/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1

    Affordable rates and amazing oceanfront views, that’s what...

  24. Sleeps 5, $200 to $225/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    Affordable rates and amazing oceanfront views, that’s what...

  25. Sleeps 6, $205 to $230/night

    City : Princeville
    Bedrooms : 3
    Bathrooms : 3

    The Villas on the Prince is a gated community with nearby access to...

  26. Sleeps 6, $375 to $460/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    Could you ask for anything more- eight tennis courts, two swimming...

  27. Sleeps 10, ~$565/night

    City : Koloa
    Bedrooms : 4
    Bathrooms : 5

    Spacious elegant 4br Poipu home with pool, close to south shore...

  28. Sleeps 4, $155 to $200/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    Puamana 3A has a spacious 1550sf of living space surrounded by the...

  29. Sleeps 6, $205 to $605/night

    City : Waikoloa
    Bedrooms : 2
    Bathrooms : 2

    Luxurious and spacious, two bedroom, two bathroom, with lanai,...

  30. Sleeps 6, $285 to $400/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2

    Pu’u Po’a 102 is located on the bluff of Princeville with...