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.

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  • '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
    119  reviews
    from $204 
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  • Spend the Winter Holidays 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
    44  reviews
    from $1,358 
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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
    137  reviews
    from $199 
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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.

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

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    96  reviews
    from $309 
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  • Lanikai Beach Front-Lic #90/TVU-0042 - Views, Beach, 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
    112  reviews
    from $1,900 
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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
    12  reviews
    from $600 
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  • Kailua Beachfront SHORT-TERM LICENSED RENTAL - Amazing Views, Spacious Home

    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
    191  reviews
    from $1,900 
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  • Steps to Lanikai Beach~3 living spaces w/heated pool, hot tub: Sleeps 14.

    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
    18  reviews
    from $774 
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  • Kailua Beachfront~private~newly renovated home w/stunning views & spa

    This casual Kailua Beach house will transport and inspire you with its panoramic ocean views and is available to be rented for periods of 30 days or more at any one time. The 3 main bedrooms, living room and dining spaces offer incredible sites...
    Registration Number: GE-023-497-1136-03, TA-023-497-1136-03

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    6  reviews
    from $800 
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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
    101  reviews
    from $135 
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  • Steps to Beach-Heated Pool-A/C-Gated Comunty-7 Nite Min-ASK OWNER Availability

    This beautiful four bedroom (two luxury master suites, one guest suite and guest bedroom, all air conditioned), four bath Hawaiian style home is just a short walk to pristine Kailua Beach.

    This spacious, estate quality home offers serene ...
    Registration Number: TA-065-681-2032-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    98  reviews
    from $850 
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  • 1 Bedroom AC Modern Walk to Kailua 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
    25  reviews
    from $179 
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  • Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2024 dates!

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

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    88  reviews
    from $825 
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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
    11  reviews
    from $630 
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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
    127  reviews
    from $320 
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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
    6  reviews
    from $840 
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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
    130  reviews
    from $295 
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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

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    33  reviews
    from $520 
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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
    5  reviews
    from $600 
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  • Awesome Beachside Cottage Located Just Steps Away from Kailua Beach

    Tropical setting just steps away from beautiful Kailua Beach. Located on a quiet cul-de-sac beachside of Kalaheo Ave. This quiet and private accommodation is ideal for 2 couples or a small family. Aprox 900sq ft of indoor living area, complete ...
    Registration Number: TA-036-719-8208-01, GE-036-719-8208-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> kailua
    117  reviews
    from $295 
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  • Gorgeous Lankai Villa with Access to Secluded White Sand Beach

    This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we ...
    Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

    • 5 bedroom
    • 5 bathroom
    • Sleeps 15
    Hawaii> Kailua
    28  reviews
    from $3,563 
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  • Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

    Only steps to beach through private street gate, and a short 1.5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok....
    Registration Number: 430180410000, TA-199-189-0944-01, GE-199-189-0944-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua
    6  reviews
    from $280 
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  • Gorgeous Oceanfront Home w/Mokulua Isle Views, Yard & AC: Lanikai Oceanside

    With front row seats to the ocean and the famous Mokulua Islands of Kailua, Lanikai Oceanside offers the best seats in the house. Newly renovated, this tropical chic and modern oceanfront beach home is open and spacious, yet warm and intimate. ...
    Registration Number: GE-141-510-3488-01, 430030630000, TA-141-510-3488-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    10  reviews
    from $875 
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  • Adorable Beachfront Home Located on Secluded White Sand Beach!

    Hale Mahina is a lovely beach home located on a pristine, secluded white sand beach that can only be accessed by a few houses on the property, or by boat. Everywhere you look is the sparkling ocean. Wake up each morning to a glorious sunrise to ...
    Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

    • 4 bedroom
    • 5 bathroom
    • Sleeps 10
    Hawaii> Kailua
    86  reviews
    from $1,650 
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  • Private Beachfront Rental

    2 Night Minimum Stay
    10 night Maximum Stay

    Our Hawaiian Style Vacation Rental apartment is located on Kailua Beach, one of Hawaii's most beautiful of white sand beaches. Kailua Beach has been rated tops among USA's best beaches. ...
    Registration Number: GE-168-049-0496-01, 430180480000, TA-168-049-0496-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    198  reviews
    from $330 
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  • Kailua Oceanfront - Contact host for Thanksgiving Week Special

    Kaimalino Kai is a two story, 3 bedroom, 4 full bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement the elegant ...
    Registration Number: 440390160000, GE-097-705-3696-01, TA-097-705-3696-01

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua
    102  reviews
    from $810 
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  • Private, beachfront apartment in Lanikai with stunning ocean views!

    *Our calendar may not reflect our current availability. Please feel free to reach out with any questions regarding quotes for our monthly rates, fees and availability at lanikaisunrise808@gmail.com

    Perfectly situated and private with ...
    Registration Number: 430050510000, GE-183-951-1552-01, TA-183-951-1552-01

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    48  reviews
    from $285 
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  • Oceanfront Lanikai Home with Access to Secluded White Sand Beach

    Hale Melia - This four bedroom, four bathroom home is ideal for families. It features high vaulted ceilings, a large open living space, plenty of dining areas, a perfectly manicured yard, and access to a gorgeous white sand beach just yards ...
    Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Kailula
    31  reviews
    from $1,463 
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  • Steps to Beach Heated Pool Air Conditioned 7 Night Min ASK OWNER Availability

    Hale Kea is a newly renovated Hawaiian-style home designed for casual living and family entertainment; just steps to beautiful Kailua Beach.

    There are two master bedrooms with in suite bathrooms and a guest bedroom with a double bed. All...
    Registration Number: 430100170000, TA-065-681-2032-01, GE-065-681-2032-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 5
    Hawaii> Kailua
    52  reviews
    from $750 
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  • Best Price and Location on Beautiful Kailua Beach!

    The upstairs and downstairs beach front studios..My beach front studios for 2 guests are located right on beautiful sandy Kailua Beach. they are quiet with private entrances and private bathrooms, modern, spacious and tastefully furnished. The ...
    Registration Number: 430150470000, GE-027-534-9504-02, TA-027-534-9504-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    111  reviews
    from $265 
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