Kailua Vacation Rentals

Kailua is one of the most popular vacation rental destinations on Oahu, featuring a fantastic white-sand beach. Many of the vacation rental properties in Kailua are oceanfront, which makes Kailua the perfect destination for those looking for privacy or a romantic getaway. You can have your privacy here and in the same time enjoy easy access to shopping malls, restaurants and services. Kailua Beach is ideal for swimming, kayaking and windsurfing. Browse through this fine selection of Kailua vacation rentals below and find your perfect home away from home.

  • 'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.

    "In order to comply with Oahu's 30 day minimum short term rental laws, we may not advertise to rent for a period shorter than 30 days."

    Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully ...
    Registration Number: 420200410000, TA-071-652-3520-01, GE-071-652-3520-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    from $218 
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  • licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage

    Charming beachfront cottage right on Kailua Beach!

    licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ...
    Registration Number: TA-096-237-9776-01, GE-096-237-9776-01, 430120130000

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    from $954 
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  • Kailua Beach Vacation Cottage

    *Please read full description!

    Sleeping 6, our large private garden cottage is located just 50 steps away from Kailua Beach. The lush garden setting offers a large air conditioned bedroom that sleeps 4 (queen size bed and 2 twin beds), ...
    Registration Number: TA-065-131-7248-01, GE-065-131-7248-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    from $368 
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  • Spend October Just 40 Steps to a Beautiful White Sand Beach n

    Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai overlooks the beautiful beach, Kailua Bay, and Offshore Islands.

    Kailua is a small upscale ...
    Registration Number: TA-191-191-0400-01, GE-191-191-0400-01, 430130460000

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Kailua
    from $1,828 
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  • Escape & Treat Yourself..Quiet Clean Bright..5 star reviews, Sleeps 4

    Aloha, this unique Premier Partner property is exclusively available for rental for periods of thirty (30) days or more. Questions, please contact us for the dates you are interested in and we will respond wiki-wiki (fast !).

    This is ...
    Registration Number: 420480020000, TA-120-590-3360-01, GE-120-590-3360-01

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua
    from $273 
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  • Charming Lanikai Cottage. Contact Owner for Availability and Custom Dates!

    Calendar may not reflect accurate availability. Please contact owner with custom requests. 8085547738

    Enjoy this lovely and elegant cottage, one short block from world famous Lanikai beach! This beautiful cottage boasts stunning acacia ...
    Registration Number: TA-123-607-8592-01, GE-123-607-8592-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    from $389 
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  • Lanikai Beachfront - Spectacular Views; Legal Short-term Rental

    Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and ...
    Registration Number: 430080930000, TA-043-470-0288-01, GE-043-470-0288-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 14
    Hawaii> Kailua
    from $3,465 
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  • Large Home With Pool Just Steps to Kailua Beach

    Set on a private road with private beach access, Kailua Beachside is One-Story Home a 4BD/4BA (over 2,800 square feet) estate home that has been extensively remodeled and well-cared for. Nestled amongst mature landscaping, the property offers ...
    Registration Number: 430180560000, TA-196-376-7808-01, GE-196-376-7808-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 14
    Hawaii> Kailua
    from $827 
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  • Amazing & Large Kailua Beachfront for up to 14 guests

    Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half ...
    Registration Number: GE-060-877-8240-01, 430210250000, TA-060-877-8240-01

    • 5 bedroom
    • 6 bathroom
    • Sleeps 14
    Hawaii> Kailua
    from $2,681 
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  • Lanikai Beach~3 living spaces w/heated pool, spa: Sleeps 14. FALL RATES

    With 3 separate living spaces, this remodeled Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern ...
    Registration Number: GE-005-853-7984-01, TA-005-853-7984-01

    • 5 bedroom
    • 6 bathroom
    • Sleeps 14
    Hawaii> Kailua
    from $983 
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  • Come relax on the lake! Beautiful lake and mountain views. Kayaks included.

    Contact host for updated calendar. Come and experience life on the lake! This 750 sq ft, second floor one bedroom, one bath with kitchenette, private lanai and private entrance is just what you are looking for. Located in a nice, quiet ...
    Registration Number: GE-064-829-8496-01, TA-064-829-8496-01, 420610170000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    from $167 
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  • Steps to Beach-Heated Pool-Air Con-Gated Community-CONTACT HOST Weekly Rates

    Click ‘Check Availability’ for online calendar. Unblocked days are available. Click ‘Contact Host’ for reservation request. Seven night minimum stay.

    This beautiful four bedroom, four full bath air conditioned Hawaiian style home ...
    Registration Number: TA-065-681-2032-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    from $1,028 
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  • 1 Bedroom AC Modern 5 Min Walk Beach

    Turn key ready for a relaxing stay.

    With on site parking, a common use gated entrance leads you down a lava rock pathway to a private gated courtyard that contains a BBQ, water feature, patio table & chairs and lighted umbrella to enjoy ...
    Registration Number: 143024003000, GE-111-409-1520-01, TA-111-409-1520-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    from $204 
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  • Beachside Kailua AC 3min walk to beach! Inquire for available dates!

    This airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home. Whether you prefer lounging in the sun alongside the ...
    Registration Number: 430190530000, GE-126-659-1744-01, TA-126-659-1744-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    from $996 
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  • Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC

    Nestled in the highly sought after wonderful Lanikai community, this beautiful executive home was newly built in 2014. This home is a perfect vantage point.

    It boasts 3 bedrooms en suite that are generous in size and more than ample in ...
    Registration Number: 430050050000, TA-209-884-5696-01, GE-209-884-5696-01

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    from $574 
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  • Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

    Due to local laws we have a rental contract of 30 days.

    This beautiful, spacious Kailua home has 3 bedrooms and 2 bathrooms. The house can sleep up to 6. Two bedrooms have a King bed and one bedroom has two twin beds. There is also ...
    Registration Number: TA-143-873-0240-01, 430750280000, GE-143-873-0240-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    from $399 
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  • Kailua Beach Hideaway TA-189-305-8560-01

    Beachfront! The White Sand of Kailua Beach at Your Door!
    This 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven.
    Tucked away and private, this home embodies the true island lifestyle.
    Walk or jog the long stretch of beach...
    Registration Number: GE-189-305-8560-01, TA-189-305-8560-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    from $1,111 
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  • Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

    Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua. The owners live on the property in the main house.
    The cottage is a 600 square foot 1 ...
    Registration Number: 143072028000, GE-058-690-1504-01, TA-058-690-1504-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    from $304 
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  • Lanikai Ocean Front Duplex Bungalow. Awesome! Private ocean access.

    Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views from the ocean front yard, the living room, dining room, and side deck.

    A perfect place...
    Registration Number: TA-139-440-7424-01

    • 3 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    from $462 
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  • Steps To Kailua Beach


    Our beautiful home has been featured in Hawaii Home Magazine and has received a best in class award from the Hawaii Builders Association. The home is within a 2 minute walk to Kailua Beach Park, the Kalapawai Market and Buzz's Steak ...
    Registration Number: GE-030-384-5376-01, TA-030-384-5376-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Kailua
    from $720 
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