Hawaii Vacation Rentals - 1070 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 16, $8750 to $13750/night

    City : Honolulu
    Bedrooms : 7
    Bathrooms : 7.5
    Pool Hot Tub

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

  2. Sleeps 16, $7815 to $12500/night

    City : kailua
    Bedrooms : 8
    Bathrooms : 8.5
    Pool

    Royal Beach Estate is one of the newest, most striking and...

  3. Sleeps 14, $7500 to $9000/night

    City : Kailua
    Bedrooms : 7
    Bathrooms : 10
    Pool

    The Paul Mitchell Estate is situated in a 1.3 acre security-gated,...

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

    City : Kailua
    Bedrooms : 5
    Bathrooms : 6
    Pool Hot Tub

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

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

    City : Honolulu
    Bedrooms : 6
    Bathrooms : 6.5
    Pool Hot Tub

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

  6. Sleeps 12, $4625 to $7500/night

    City : Kilauea
    Bedrooms : 7
    Bathrooms : 7.5

    Between the mystical mountains and renowned Secret Beach, The Secret...

  7. Sleeps 8, $4315 to $4565/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    Retreat to Island Living in this award winning architectural home...

  8. Sleeps 18, $4065 to $7250/night

    City : Kula
    Bedrooms : 9
    Bathrooms : 9
    Pool

    This private, gated estate sits on over 17 acres overlooking all of...

  9. Sleeps 10, ~$4000/night

    City : Kailua-Kona
    Bedrooms : 5
    Bathrooms : 5
    Pool

    This beautiful 5 bedroom, 5 bath home is newly designed and built in...

  10. Sleeps 10, $3970 to $11190/night

    City : Waimea
    Bedrooms : 5
    Bathrooms : 5.5
    Pool

    Artevilla is a brand new, luxury, two story, five bedroom, ocean...

  11. Sleeps 20, $3750 to $4565/night

    City : Waimanalo
    Bedrooms : 9
    Bathrooms : 7
    Pool

    The Royal Hawaiian Estate provides the ideal Hawaiian vacation....

  12. Sleeps 12, ~$3750/night

    City : Hanalei
    Bedrooms : 6
    Bathrooms : 6

    Hanalei Dolphin Estate is beachfront luxury at its finest. This...

  13. Sleeps 12, $3750 to $4375/night

    City : Waimea
    Bedrooms : 6
    Bathrooms : 8
    Pool

    Honuala`i sits on the shores of a calm, protected bay in Puako, on...

  14. 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...

  15. Sleeps 12, $3565 to $4250/night

    City : Kilauea
    Bedrooms : 5
    Bathrooms : 5.5
    Pool

    Imagine whiling away your dream Hawaiian vacation at this expansive...

  16. Sleeps 6, $3500 to $6250/night

    City : Paia
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Banyan Cove is a 7,800 square foot, three+bedroom home, situated on...

  17. Sleeps 10, ~$3375/night

    City : Kilauea
    Bedrooms : 5
    Bathrooms : 5.5
    Pool

    Welcome to Hale Mana, one of Kauai's most beautiful island...

  18. Sleeps 10, $3300 to $4400/night

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

    Perfectly located on the Kona "Gold Coast" of the Big Island, this...

  19. Sleeps 10, $3125 to $4375/night

    City : Kilauea
    Bedrooms : 4
    Bathrooms : 3.5
    Pool

    A secluded and serene modern Balinese-style estate located on the...

  20. Sleeps 10, $3000 to $4750/night

    City : Honolulu
    Bedrooms : 5
    Bathrooms : 5.5
    Pool

    Welcome Home to "Moana Lani"! Are you ready for a truly private and...

  21. Sleeps 10, $2865 to $12090/night

    City : Lahaina
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    The private grand residences at Montage Kapalua Bay represent the...

  22. Sleeps 8, $2815 to $3125/night

    City : Kailua-Kona
    Bedrooms : 3
    Bathrooms : 3

    Located just a few tenths of a mile from the Four Seasons Hualalai...

  23. Sleeps 12, $2750 to $3750/night

    City : Waimea
    Bedrooms : 6
    Bathrooms : 6.5
    Pool

    MELE KOHALA, which means Song of Kohala, is an 8,000 square foot...

  24. Sleeps 10, $2750 to $3750/night

    City : Kilauea
    Bedrooms : 5
    Bathrooms : 5
    Pool

    The spacious living room features a comfortable seating area, grand...

  25. Sleeps 8, $2685 to $10090/night

    City : Lahaina
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    The private grand residences at Montage Kapalua Bay represent the...

  26. Sleeps 8, $2500 to $2750/night

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Many incredible upgrades have been made to this gorgeous home and...

  27. Sleeps 6, $2500 to $3125/night

    City : Princeville
    Bedrooms : 4
    Bathrooms : 4.5

    Nestled on a spectacular ocean bluff, this exquisitely designed...

  28. Sleeps 10, $2500 to $3125/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 5.5
    Pool

    Located on the pristine and perennially sunny shores of Puako, a...

  29. Sleeps 8, $2495 to $3440/night

    City : Waikoloa Village
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    The 'Blue Wave' house is a one-of-a-kind oceanfront estate in the...

  30. Sleeps 8, $2440 to $2720/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 4.5
    Pool

    Located in an intimate gated community in the heart of Mauna Kea...