Kailua: Vacation Rental By Owner

Showing 20 Of 249 Vacation Rentals
  • Property-1 Image 1
    House Select Dates for Price
    • 5 Bed
    • 4 Baths
    Kailua, HI

    4 Bedrooms + Loft, 4 Baths, (Sleeps 8-10) with 2 large master suites! Loft now has AC!!! All of the other rooms have dedicated AC units and there is a master AC... ...more

  • Property-2 Image 1
    House $437 / Nightly
    • 3 Bed
    • 3 Baths
    • (107)
    Kailua, HI

    Aloha! Please note that due to difficult travel circumstances we have changed our cancellation policy to allow for a cancellation and full refund at ANY TIME.... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (65) Exceptional
    Kailua, HI

    Hale Kainalu is a sweet getaway at the end of Lanikai with exclusive secluded beach used by only 5 houses within a gated drive. This beautiful cottage is... ...more

  • Property-4 Image 1
    Condo $219 / Nightly
    • 1 Bed
    • 2 Baths
    • (60) Excellent
    Kailua, HI

    Immaculate, beautifully furnished unit in great location. Wheel chair accessable, short walk to restaurants, shopping, and ocean activities. Solid concrete... ...more

  • Property-5 Image 1
    House $831 / Nightly
    • 4 Bed
    • 3 Baths
    • (41)
    Kailua, HI

    By Settlement Agreement, Oahu vacation homes are permitted to rent to one guest per month. We require a seven night minimum stay. This property is a legally... ...more

  • Property-6 Image 1
    Apartment $113 / Nightly
    • 1 Bed
    • 1 Baths
    • (84)
    Kailua, HI

    FOR STAYS OF 30 DAYS OR MORE: Hale O KuhiKuhi HiHi' O -- 'Ha Lay O Coo Hee Coo Hee Hee Hee O' Aloha and Welcome to the 'House of Sweet Dreams.' If you were... ...more

  • Property-7 Image 1
    House $282 / Nightly
    • 2 Bed
    • 3 Baths
    • (37) Excellent
    Kailua, HI

    The Master Suite in this house will take your breath away and is on a third story all to its own. It is hard to decide what is more beautiful ... the Ocean Views... ...more

  • Property-8 Image 1
    House $963 / Nightly
    • 3 Bed
    • 3 Baths
    • (51) Wonderful
    Kailua, HI

    Hawaii is NOW OPEN to all travelers with a pre-flight Covid-19 test starting August 1st, 2020! Please note: We accept only one stay per 30-day rental period. OUR... ...more

  • Property-9 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (53)
    Kailua, HI

    Picture yourself in Paradise. That's where you'll be while you're enjoying an unforgettable vacation at Casa de Emdeko unit 232. Swimming, surfing, sunbathing,... ...more

  • Property-10 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (86) Excellent
    Kailua, HI

    Aloha! Come see for yourself why the gated community of Casa De Emdeko remains one of the most requested oceanfront condominiums along the Kona Coast. Casa #328... ...more

  • Property-11 Image 1
    House $497 / Nightly
    • 1 Bed
    • 1 Baths
    • (91) Excellent
    Kailua, HI

    Hear the waves crashing on the shoreline of this uncrowded oceanfront paradise Upscale quiet neighborhood on the North end of Kailua - Away from the... ...more

  • Property-12 Image 1
    House $392 / Nightly
    • 1 Baths
    • (105) Excellent
    Kailua, HI

    Kailua oceanfront deluxe vacation rentals - two units located in an oceanfront home in Kailua on the directly on the ocean. None closer in Kailua The studio unit... ...more

  • Property-13 Image 1
    House $3,921 / Nightly
    • 5 Bed
    • 6 Baths
    • (7) Exceptional
    Kailua, HI

    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists... ...more

  • Property-14 Image 1
    House $2,035 / Nightly
    • 4 Bed
    • 4 Baths
    • (10) Exceptional
    Kailua, HI

    Enjoy peace and tranquility from this beautifully remodeled home while soaking in the endless, unobstructed views of the Pacific Ocean and Mokulua Islands. This... ...more

  • Property-15 Image 1
    House $1,740 / Nightly
    • 3 Bed
    • 3 Baths
    • (4) Very Good
    Kailua, HI

    Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush... ...more

  • Property-16 Image 1
    House $3,141 / Nightly
    • 4 Bed
    • 4 Baths
    • (1) Exceptional
    Kailua, HI

    This ocean front home with inspiring views and coastal access is located in a private, quiet cul-de-sac at the tip of Kailua Bay, two miles from Kailua Beach.... ...more

  • Property-17 Image 1
    House $317 / Nightly
    • 3 Bed
    • 2 Baths
    • (10) Wonderful
    Kailua, HI

    Experience oceanfront living from this charming beach home. The backyard opens up to the world renowned Lanikai Beach, with soft white sands, picturesque horizon,... ...more

  • Property-18 Image 1
    House $1,167 / Nightly
    • 3 Bed
    • 3 Baths
    Kailua, HI

    Licensed TVU 90/TVU-0142 GiGi’s retreat is located on the shore of world famous Kailua Beach. Bring the whole family for a much needed vacation. having the... ...more

  • Property-19 Image 1
    Villa Select Dates for Price
    • 5 Bed
    • 5 Baths
    Kailua, HI

    A 30 day minimum lease is required for any rentals. Awesome beach front villa with pool and hot top. Wake up to amazing sunrises and go for a quick swim or run at... ...more

  • Property-20 Image 1
    House $1,662 / Nightly
    • 4 Bed
    • 5 Baths
    • (42)
    Kailua , HI

    RECENT CANCELLATIONS HAVE HAVE OPENED OUR BEACHFRONT HOME FROM MARCH 20 THROUGH THE SUMMER. THE PREVAILING TRADE WINDS IN HAWAII COME FROM ALASKA, 2880 MILES... ...more

loader

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Kailua. Many accommodations in Kailua provide "Non Smoking Only", there are 178, or there are 174 of Vacation Rentals in Kailua with a "Pets Not Allowed", there are also 157 with "Surfing", which is another great reason to visit Kailua.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Kailua. The most expensive month of the next 12 months is in July, where prices hit an average of $751 a night. In June, prices will hit an average low of $740 per night.