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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  • Beautiful Tropical Home Close to Beach w/Pool, Yard & AC: Hale Nani Lanikai

    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: TA-209-884-5696-01, GE-209-884-5696-01, 430050050000

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    11  reviews
    from $706 
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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: TA-189-305-8560-01,+GE-189-305-8560-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    5  reviews
    from $400 
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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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  • 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 $3,783 
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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
    5  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: 430030630000, TA-141-510-3488-01, GE-141-510-3488-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    10  reviews
    from $911 
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  • Steps To Kailua Beach - Heated Pool - Air Conditioned - 7 Night Minimum Stay

    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: GE-065-681-2032-01, TA-065-681-2032-01, 430100170000

    • 3 bedroom
    • 3 bathroom
    • Sleeps 5
    Hawaii> Kailua
    50  reviews
    from $750 
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  • Newly Renovated Designer Cottage- Private Yard & Deck- 5 Min to Kailua Beach

    Tropical Paradise with your own yard... Over 800 square feet of living.

    Our newly renovated cottage is the perfect getaway located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just ...
    Registration Number: TA-133-517-5168-01,+GE-133-517-5168-01

    • 0 bedroom
    • 1 bathroom
    • Sleeps 3
    Hawaii> Kailua
    21  reviews
    from $179 
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  • The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!

    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 literally right on the beach & overlooks the crystal clear, blue and green hued water. Wake...
    Registration Number: GE-180-925-6448-01,TA-180-925-6448-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    72  reviews
    from $1,129 
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  • Enjoy watching for Sea Turtles off your Ocean Front Deck!

    TA-006-302-3104-01

    Beautiful ocean front home at the beginning of Oahu's famous Lanikai Beach!. 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with ...
    Registration Number: GE-006-302-3104-01,TA-006-302-3104-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Kailua
    2  reviews
    from $1,680 
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  • Kakela Kai, Beachfront Kailua Home, Private, A/C

    A comfortable beachfront home set in a security-gated neighborhood with central air condition. Decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile, granite counters and wooden flooring. There is a ...
    Registration Number: 430180100003, TA-083-865-6000-01, GE-083-865-6000-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Kailua
    13  reviews
    from $675 
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  • Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach

    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze. Built in 2017, this brand new construction boasts upgraded appliances and furnishings meticulously hand picked by local designer, Lotus Home Staging. ...
    Registration Number: GE-135-880-0384-01, 430070810000, TA-135-880-0384-01

    • 5 bedroom
    • 5 bathroom
    • Sleeps 10
    Hawaii> Kailua
    8  reviews
    from $606 
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  • Fabulous Luxury Kailua Beachfront Private pool and Hot Tub

    VIEWS!! Absolutely beautiful right on Kailua beach with pool and spa .

    Six bedrooms of beach-front paradise in Kailua. Swimming pool, hot tub, game and TV room make this property an ideal vacation recreation ...
    Registration Number: TA-095-587-3792-01, GE-095-587-3792-01, 430830080000

    • 5 bedroom
    • 5 bathroom
    • Sleeps 12
    Hawaii> Kailua
    2  reviews
    from $1,995 
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  • Licensed Lanikai Beach Rental 100 yards to Lanikai Beach w/AC!

    Indulge in the tranquility of Lanikai Beach, just a stone's throw away, and let the allure of this coastal paradise wash over you. With the studio's inviting comforts and the endless ocean possibilities at your disposal, your stay promises to be...
    Registration Number: GE-095-917-0560-01, 143005018000, TA-095-917-0560-01

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    38  reviews
    from $357 
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  • Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!

    This Kailua, beachside, pool home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!

    Each room has an individually ...
    Registration Number: GE-174-185-2672-01, TA-174-185-2672-01, 430190450000

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    6  reviews
    from $1,001 
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  • Orchid House | New Low Promo Rates for SPRING and SUMMER 2023!!

    ORCHID HOUSE
    TA # 087-311-0016-01

    With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors,...
    Registration Number: GE-087-311-0016-01,TA-087-311-0016-01

    • 3 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Kailua
    1  reviews
    from $781 
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  • Exquisite Oceanfront Retreat w/Mokulua Views, AC & Lush Yard: Lanikai Seashore

    Experience luxurious coastal living at Lanikai Seashore, a tropical two-story vacation rental just steps away from the renowned Lanikai Beach. This villa’s spacious open floor plan and unobstructed ocean views makes one feel they’re almost ...
    Registration Number: 430050620000, TA-151-764-5824-01, GE-151-764-5824-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Kailua
    1  reviews
    from $1,207 
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  • Studio Walk To Beach Modern A/C King Bed

    30 Night Minimum Stay.
    Turn key ready.
    Well appointed, private and serene studio apartment within walking distance to beach.
    Parking on site.

    Ideal for a single person or a couple.

    Upon entry, you will be welcomed into a ...
    Registration Number: 143024003000, GE-111-409-1520-01, TA-111-409-1520-01

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    2  reviews
    from $149 
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  • Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua

    Let the relaxing atmosphere of Lokomaika’i Kailua (meaning Gracious Kailua) whisk you into vacation mode. The home includes 2 primary suites that beckon you to the outdoor areas of the pool and garden. There are also 2 additional bedrooms and ...
    Registration Number: TA-079-127-1936-01, GE-07

    • 5 bedroom
    • 3 bathroom
    • Sleeps 11
    Hawaii> Kailua
    1  reviews
    from $913 
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  • Bright Kailua Retreat w/hot tub, Lush Pool, Walk to Beach: Hale Ohana

    Hale Ohana meaning Family House is just that! With multiple lounge areas, pool, hot tub, game room inclusive of a spider man pinball game, ping pong table and much more this home is perfect for a family get away! The home includes 3 bedrooms in ...
    Registration Number: GE-139-302-3488-01, TA-139-302-3488-01, 430830350000

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Kailua
    1  reviews
    from $1,133 
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  • Kailua Guest Suite

    Beautiful attached guest suite. This Private guest suite has a full kitchen, washer/dryer, stainless steel appliances and a walk in glass shower. It has its own separate private entrance. There is also plenty of street parking. The suite is a ...
    Registration Number: TA-195-394-1594-02,+GE-195-394-1504-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    Hawaii> Kailua
    12  reviews
    from $154 
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  • Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

    One of the original homes on Kailua Beach, this Renovated 1937 five bedroom Cottage is just one house from the middle of Kailua Beach, the #1 Beach in the world.  Nestled between a park and a lightly used club with only one beachfront neighbor,...
    Registration Number: GE-045-319-8848-01, TA-045-319-8848-01, 430160220000

    • 5 bedroom
    • 2 bathroom
    • Sleeps 10
    Hawaii> Kailua
    3  reviews
    from $2,669 
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  • Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option

    Aloha and Welcome to Kolea Landing
    A short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom ...
    Registration Number: 430070230000, GE-082-679-2448-01, TA-082-679-2448-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    68  reviews
    from $610 
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  • Luxury 2 bd 2 bath - world famous Lanikai Beach - less than 5 min walk to water!

    ** Calendar may not always have latest available dates or be updated. Hale Anuenue i Lanikai may be available - always reach out to us on the 'contact host' link for best and latest information **

    A warm ALOHA and E KOMO MAI (welcome)! ...
    Registration Number: 430030070000, GE-067-636-2752-01, TA-067-636-2752-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua
    15  reviews
    from $300 
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  • Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

    Welcome to Lanikai Hale ~ Two Hawaiian style cottages (which can be rented together or separately) on a large fenced-in property in the heart of Lanikai, just 2 miles from Kailua Town on the Windward side of Oahu.
    There is plenty of parking ...
    Registration Number: TA-107-927-8080-01,+GE-107-927-8080-01

    • 5 bedroom
    • 3 bathroom
    • Sleeps 12
    Hawaii> Kailua
    23  reviews
    from $995 
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  • Spectacular Beachfront Kailua home w/heated pool. Newly Renovated (2023)!

    Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking ...
    Registration Number: GE-176-489-9328-01, TA-176-489-9328-01, 1430200510000

    • 6 bedroom
    • 7 bathroom
    • Sleeps 14
    Hawaii> Kailua
    1  reviews
    from $2,823 
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  • New to the market! Private Villa w/Pool, AC, walk to beach: Villa Hui Hou

    The ultimate beach lifestyle awaits you at idyllic Villa Hui Hou on O’ahu’s scenic windward coast. Located off the main strip in the exclusive neighborhood of Lanikai, this recently remodeled five bedroom, four and a half bathroom property ...
    Registration Number: 430030440000, GE-091-214-0288-01, TA-091-214-0288-01

    • 5 bedroom
    • 5 bathroom
    • Sleeps 12
    Hawaii> Kailua
    1  reviews
    from $642 
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  • Large, beautiful, updated home w/pool, AC, mins from beach in Kailua!

    Welcome to Holoholo Hale in the beautiful town of Kailua on the island of Oahu. Kailua is the home of two of the best beaches in the world, Kailua Beach Park and Lanikai Beach. The home is a short drive to all the island has to offer including ...
    Registration Number: GE-141-882-0096-01, TA-141-882-0096-01, 420560420000

    • 7 bedroom
    • 4 bathroom
    • Sleeps 14
    Hawaii> Kailua
    18  reviews
    from $1,200 
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  • 3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai

    The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's ...
    Registration Number: GE-036-329-7280-01, 420540580000, TA-036-329-7280-01

    • 6 bedroom
    • 4 bathroom
    • Sleeps 18
    Hawaii> Kailua
    2  reviews
    from $945 
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  • 3 bedroom 2 bathroom single family home in Kailua Beach Town

    The Home
    Our home is your home. With a fenced back yard, and plenty of spaces to relax including our covered lanai, you can sip a cocktail, read your novel and enjoy the Hawaiian sunshine in total relaxation.

    Your family will be close ...
    Registration Number: 430670160000, GE-011-101-1840-01, TA-011-101-1840-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    1  reviews
    from $250 
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