Big Island Vacation Rentals - 48 Properties

RedAwning’s Big Island vacation homes both include instant online booking and no security deposits, to make your trip easy and stress-free. The youngest and largest of the Hawaiian islands, the Big Island is home to an active volcano, the tallest sea mountain in the world, and countless beautiful beaches. Book your stay today!

Search results

  1. 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,...

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

    City : Kailua
    Bedrooms : 5
    Bathrooms : 6
    Hot Tub

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

  3. 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...

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

    City : Kailua-Kona
    Bedrooms : 3
    Bathrooms : 4

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

  5. Sleeps 10, $3125 to $5000/night

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

    Perfectly located on the Kona Gold Coast, enter the world of Hale...

  6. 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...

  7. 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...

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

    City : Kilauea
    Bedrooms : 5
    Bathrooms : 5
    Pool

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

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

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

  10. 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...

  11. Sleeps 8, $2090 to $2750/night

    City : Puako
    Bedrooms : 4
    Bathrooms : 4.5

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

  12. Sleeps 10, $1970 to $3440/night

    City : Kailua
    Bedrooms : 4
    Bathrooms : 3
    Pool

    Just remodeled, beautiful vacation rental home at the beginning of...

  13. Sleeps 8, $1565 to $2315/night

    City : Kailua
    Bedrooms : 4
    Bathrooms : 3.5

    This Kailua waterfront home was built in 1993 to fit the beach...

  14. Sleeps 8, $1500 to $1625/night

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3
    Pool

    One of the largest floor plans of any villa at Hualalai, this...

  15. Sleeps 6, $1500 to $1625/night

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Located on popular Waiulu Street just three minutes by golf cart to...

  16. Sleeps 6, $1500 to $1625/night

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

    Spectacular three bedroom, three bath, two-story town home on...

  17. Sleeps 8, $1500 to $2875/night

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally...

  18. Sleeps 8, $1250 to $1345/night

    City : Hōlualoa
    Bedrooms : 3
    Bathrooms : 3
    Pool

    ​Experience the ultimate in style, function and form at this...

  19. Sleeps 8, $1125 to $1625/night

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

    Spectacular three bedroom three bath villa centrally located within...

  20. Sleeps 4, $1125 to $1375/night

    City : Kailua-Kona
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Upper level 2-bedroom villa overlooking the 15th tee of the Hualalai...

  21. Sleeps 14, $1125 to $3750/night

    City : Kailua
    Bedrooms : 5
    Bathrooms : 4

    Welcome to the world of John Walker. A Scotsman who made his way to...

  22. Sleeps 8, $1100 to $2200/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 4

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

  23. Sleeps 4, ~$1065/night

    City : Kailua-Kona
    Bedrooms : 2
    Bathrooms : 2
    Pool

    One of the most beautifully appointed villas at Hualalai Resort....

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

    City : Waimea
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

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

  25. Sleeps 6, $615 to $1035/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Built in 2006, these luxurious 3 bedroom, 3 bath condominiums and...

  26. Sleeps 8, $535 to $690/night

    City : Waimea
    Bedrooms : 4
    Bathrooms : 2.5
    Pool

    Located 830 ft. above sea level on the perennially sunny Kohala...

  27. Sleeps 6, $470 to $875/night

    City : Waikoloa Village
    Bedrooms : 3
    Bathrooms : 3
    Pool

    This luxurious 3Bd/3Ba resort condominium with spectacular views is...

  28. Sleeps 8, $440 to $690/night

    City : Waikoloa Village
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Located in the serene Waikoloa Village just across the street from...

  29. Sleeps 8, $440 to $690/night

    City : Kailua-Kona
    Bedrooms : 4
    Bathrooms : 3

    This exquisitely appointed, almost beachfront home is perfectly...

  30. Sleeps 6, $415 to $765/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    3 bedroom, 3 and 1/2 baths, sleeps 6 Tropical Feel with a Luxury...