Hawaii Vacation Rentals - 510 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.

Search results

  1. Sleeps 16, $8750 to $13750/night

    City : Honolulu
    Bedrooms : 7
    Bathrooms : 7.5
    Pool

    If paradise had a home it would be here, in the sun, on the beach,...

  2. Sleeps 10, $5625 to $7500/night

    City : Kailua
    Bedrooms : 5
    Bathrooms : 6
    Pool

    "The Kailua Plantation Estate is a rare jewel that comes fully...

  3. Sleeps 12, $5000 to $6325/night

    City : Honolulu
    Bedrooms : 6
    Bathrooms : 6.5
    Pool

    This 6-bedroom/6.5 bath luxury estate is located on prestigious...

  4. Sleeps 8, $3750 to $4815/night

    City : Honolulu
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    At the forefront of the sprawling beach front estate stands the...

  5. Sleeps 6, $2245 to $5850/night

    City : Maui
    Bedrooms : 3
    Bathrooms : 4

    Ocean Bliss is a stunning beachfront estate that provides the best...

  6. Sleeps 8, $2090 to $2785/night

    City : Puako
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    Stately and serene, Hula Moon sits on one of the most beautiful...

  7. Sleeps 8, $1575 to $2290/night

    City : Kilauea
    Bedrooms : 4
    Bathrooms : 4

    King Hale is located in the serene beachfront community of Haena...

  8. Sleeps 5, $1565 to $2415/night

    City : Honolulu
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    Mesmerizing Oceanfront Diamond Head estate gracing the southern...

  9. Sleeps 8, $1250 to $1715/night

    City : Poipu
    Bedrooms : 4
    Bathrooms : 3
    Pool

    The Villas at Poipu Kai is a new boutique resort, situated in the...

  10. Sleeps 9, $1240 to $1650/night

    City : Kauai County
    Bedrooms : 4
    Bathrooms : 4.5

    If location is key then this is the one of the perfect Kauai luxury...

  11. Sleeps 8, $1210 to $1815/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 4

    This unique property is situated above beautiful Wailea Bay on the...

  12. Sleeps 8, $1125 to $1725/night

    City : Honolulu
    Bedrooms : 4
    Bathrooms : 3.5
    Pool

    East of Diamond Head and 5 mins from Hanauma Bay! Just 20 minutes...

  13. Sleeps 8, $1050 to $1915/night

    City : Hanalei
    Bedrooms : 4
    Bathrooms : 3

    Located beachfront on the enchanting Hanalei Bay, Lani Kai...

  14. Sleeps 8, $940 to $1375/night

    City : Poipu
    Bedrooms : 4
    Bathrooms : 3.5
    Pool

    "The Villas at Poipu Kai is a new boutique resort, situated in the...

  15. Sleeps 6, $845 to $1240/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 3.5

    Ali'i Villa is a stunning 3-bedroom, 3.5 bath golf-front villa,...

  16. Sleeps 4, $840 to $1650/night

    City : Hanalei
    Bedroom : 1
    Bathroom : 1

    Hale Maluhia is a one-of-a-kind beachfront home on Hanalei Bay and...

  17. Sleeps 6, $780 to $1200/night

    City : Poipu
    Bedrooms : 3
    Bathrooms : 3
    Pool

    "The Villas at Poipu Kai is a new boutique resort, situated in the...

  18. Sleeps 4, $770 to $1320/night

    City : North Kauai
    Bedrooms : 2
    Bathrooms : 2.5
    Pool

    High atop Crater Hill, Mele Makani is a lovely Estate with...

  19. Sleeps 6, $770 to $1320/night

    City : Kilauea
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    Nani Kai means glorious beautiful ocean, and it certainly lives up...

  20. Sleeps 6, $735 to $1020/night

    City : Kilauea
    Bedrooms : 3
    Bathrooms : 3
    Pool

    One of the more sought after aspects of a vacation rental (or home...

  21. Sleeps 4, $630 to $1020/night

    City : Hanalei
    Bedrooms : 2
    Bathroom : 1.5

    Welcome to Hale Nalu (Surf), an oceanfront cottage in Hanalei Bay,...

  22. Sleeps 6, $625 to $725/night

    City : Kapaa
    Bedrooms : 2
    Bathrooms : 3
    Pool

    Just renovated, H201 is the “Hee Nalu Surf Penthouse”: Nothing...

  23. Sleeps 6, $550 to $1100/night

    City : Koloa
    Bedrooms : 3
    Bathrooms : 3

    Due to construction going on behind Hale Pohaku Kai (9 to 530 Monday...

  24. Sleeps 8, $525 to $620/night

    City : Lahaina
    Bedrooms : 3
    Bathrooms : 3

    Nicely updated, ocean front 3 bedroom, 3 bathroom unit in Kahana....

  25. Sleeps 10, $495 to $855/night

    City : Koloa
    Bedrooms : 4
    Bathrooms : 4
    Pool

      *Private, fully furnished house has a fenced in yard with...

  26. Sleeps 15, $495 to $770/night

    City : Koloa
    Bedrooms : 4
    Bathrooms : 3

      Large beautiful home in the Poipu Kai neighborhood Three levels...

  27. Sleeps 6, $495 to $580/night

    City : Lahaina
    Bedrooms : 2
    Bathrooms : 2

    Two Bedroom; (One-bedroom Corner and Junior suite that connects);...

  28. Sleeps 6, $495 to $580/night

    City : Kaanapali
    Bedrooms : 2
    Bathrooms : 2

    One bedroom Corner (and junior suite that connects); King bed in...

  29. Sleeps 10, $485 to $715/night

    City : Koloa
    Bedrooms : 4
    Bathrooms : 3

      Located just one block away from world-famous Poipu and...

  30. Sleeps 8, $485 to $715/night

    City : Poipu
    Bedrooms : 4
    Bathrooms : 3

      *10 minute walk to Poipu's finest beaches *Adjacent to Shipwreck...