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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 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
    189  reviews
    from $2,500 
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  • Steps to Kailua Beach, Immaculate & Private 1 BR. Great Reviews and Value!

    30 day minimum rental due to local laws. We are truly beachside with just two houses between the suite and the private beach gate. Namala Place is a wide street with sidewalks and plenty of parking. We are situated halfway between Kalaheo ...
    Registration Number: 430200660000, GE-078-209-6384-01, TA-078-209-6384-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    Hawaii> Kailua
    36  reviews
    from $140 
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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
    86  reviews
    from $775 
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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: 430050050000, TA-209-884-5696-01, GE-209-884-5696-01

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua
    11  reviews
    from $525 
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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 $865 
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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
    194  reviews
    from $320 
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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 $350 
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  • Licensed Lanikai Garden Studio since 1985 - 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, TA-095-917-0560-01, 143005018000

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    46  reviews
    from $350 
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  • Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa

    Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 ...
    Registration Number: TA-027-765-7600-01, GE-027-765-7600-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua
    48  reviews
    from $1,500 
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  • Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

    ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1 house from the white sands of Kailua beach (Private beach gate is located adjacent to our ...
    Registration Number: TA-068-883-0976-01, GE-068-883-0976-01, 143018061000

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    27  reviews
    from $825 
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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
    26  reviews
    from $995 
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  • PRIVATE BEACHFRONT RENTAL

    Minimum Stay: 2 night
    Max Night Stay: 8 nights

    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 ...
    Registration Number: GE-168-049-0496-01, 430180480000, TA-168-049-0496-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    85  reviews
    from $320 
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  • Beautiful Beachside Bungalow

    LOCATION LOCATION LOCATION.....
    Enter Paradise
    Relax and Enjoy the Gentle Breezes of Kailua…
    The Original Kailua Beach Bungalow is elegantly renovated with a spacious open floor plan. Modern design mingles with Hawaiian tradition - ...
    Registration Number: TA-064-669-6960-02, GE-064-669-6960-02

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    11  reviews
    from $585 
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  • Coconut Grove Kailua Vacation Home

    This adorable pup-friendly, 3 bedroom, 1 bath vacation rental is ideally located, walking/biking distance to both the quaint shops and eateries of Kailua Town and renowned Kailua Beach! Fill your days with walks on the beach, surfing, SUP or ...
    Registration Number: TA-006-886-2976-01, 4306304400000, GE-006-886-2976-01

    • 3 bedroom
    • 1 bathroom
    • Sleeps 6
    Hawaii> Kailua
    1  reviews
    from $233 
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  • Luxury Coconut Grove, Kailua Vacation Home

    Bright and airy home with ample large windows to let in the fresh ocean breeze. Brand new built in 2021! Spacious rooms with a beautiful kitchen to prepare your favorite island dishes. Downstairs 3 bedroom 1 bath lockout unit also available. ...
    Registration Number: 4306304400000, TA-006-886-2976-01, GE-006-886-2976-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua
    1  reviews
    from $300 
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  • Beautiful Kailua Hale Studio

    This spacious studio is a permitted short term rental unit conveniently located in Kailua. Walking distance to Kailua Beach, Kailua Town, shopping and restaurants.

    Free on-site parking
    Memory foam queen bed.
    Full kitchenette. ...
    Registration Number: GE-121-728-3584-01, TA-121-728-3584-01, 143071110000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    45  reviews
    from $314 
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  • May-July Dates ONSALE- 6 BR/6 BA OceanFront home w/ Pool in Lanikai-Summer Dates

    If you are hoping to find that perfect estate for a 30 day+ stay, we'd love to hear from you for this or other exclusive properties. This incredible home, a few homes down from Lanikai Beach in the iconic Lanikai neighborhood, is available for 1...
    Registration Number: TA-102-425-3952-01, GE-102-425-3952-01, 430080480000

    • 6 bedroom
    • 6 bathroom
    • Sleeps 14
    Hawaii> Kailua
    2  reviews
    from $902 
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  • Luxurious Waterfront 4BR Home, Island Vibe, Private Pool, Near Kailua Beach

    Unwind at Hale Aloha by Gather, your tranquil retreat just minutes from Kailua’s famous shores. This 4-bedroom, waterfront sanctuary on a sprawling 12,000 SF combines contemporary ease with island living, presenting a lush oasis, ample spaces ...
    Registration Number: TA-195-940-3520-01, GE-195-940-3520-01, 420180550000

    • 4 bedroom
    • 2 bathroom
    • Sleeps 10
    Hawaii> Kailua
    2  reviews
    from $1,286 
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  • Omao - Kailua, Oahu - Cute Kailua Beach House - NEW RENTAL

    This beautiful Kailua home is minutes from Kailua town and walking distance to one of the most desirable beaches on Oahu.
    The property has been recently renovated and is being offered fully furnished for short term rental periods with ...
    Registration Number: 1430240090000, GE-044-037-8880-01, TA-044-037-8880-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua
    2  reviews
    from $258 
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  • Great Location, Large Pool, Koi Pond, Walk to Kailua Beach

    Our zen themed home has a beautiful koi pond courtyard and an inviting mosaic tiled swimming pool in the backyard. Each bedroom has its own private full bathroom, sitting area and AC unit. The spacious kitchen, dining room and living room are in...
    Registration Number: 430180300000, GE-096-373-7600-01, TA-096-373-7600-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kailua
    75  reviews
    from $979 
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  • Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!


    At Old Hawaii Beach House and Guest Cottage in Lanikai, we extend to all our guests the old-fashioned Hawaiian Hospitality, and the famous Spirit of Aloha.

    Step back in time to the romance, the charm, that is truly 'Old Hawaii.' ...
    Registration Number: TA-179-651-4304-01, GE-179-651-4304-01, 430040100000

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    24  reviews
    from $240 
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  • Available and legal for stays less than 30 days.

    Hawaii Sheffield House has been a legal bed and breakfast for over 30 years. We are available and legal for stays of less than 30 days.

    The Hawaii Sheffield House Ginger Studio has a 'Secret Garden. The night lighting is ...
    Registration Number: TA-137-360-9984-01, GE-137-360-9984-01, 430720040000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    86  reviews
    from $246 
      View Property   Book Now

  • NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01

    Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, ...
    Registration Number: TA-014-134-8864-01, 430260540000, GE-014-134-8864-01

    • 0 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua
    115  reviews
    from $100 
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  • Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking

    Ex 005019648001, TA 005019648001

    Our vacation hide-a-way is located in a unique community. We have named it E Komo Mai . The apartment is approximately 900 sq ft . You will have a private entry and driveway . It is easy to go and come ...
    Registration Number: 43002013, TA-005-019-6480-01, GE-005-019-6480-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    82  reviews
    from $119 
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  • Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua

    Stay in comfort as long as you wish. 30 day minimum lease, shorter stud are of longer stays are welcome. Contact Us for Details and Rates
    Hawaii Tax ID # available upon request

    Hale Pulelehua “The Butterfly House” has an open ...
    Registration Number: TA-049-642-4960-01, GE-049-642-4960-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua
    33  reviews
    from $256 
      View Property   Book Now

  • Kailua Beach "The Pink House" 100 Yards from Ocean

    The Pink House is a perfect beach house set 100 yards from beautiful Kailua Beach. This Hawaiian Style Home has an open floor plan that includes a combination living/dining area with a galley kitchen with stainless steel appliances. Recently ...
    Registration Number: TA-065-234-5344-01, GE-065-234-5344-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua
    46  reviews
    from $595 
      View Property   Book Now

  • Kailua Blue Ocean Breeze Beach Studio

    Our Kailua studio is located just three minutes walking from the most beautiful beach in the world. A gated entrance leads you down a pathway to a private gated courtyard that contains a BBQ, patio table and chairs, pool and lighted umbrella to...
    Registration Number: GE-114-432-8192-01, TA-114-432-8192-01, 430240500000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> KAILUA
    13  reviews
    from $94 
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  • Beautiful Kailua Hale 1 Bedroom

    This spacious one bedroom is a permitted short term rental located in Kailua.

    Kailua is best known for the number one best beach in the world as well as a charming Kailua town.
    Walking distance to Kailua Beach, town, shopping, ...
    Registration Number: GE-121-728-3584-01, TA-121-728-3584-01, 143071110000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    23  reviews
    from $436 
      View Property   Book Now

  • Lovely Private Kailua Cottage

    Welcome to our one bedroom permitted short term rental located in Kailua. Newly renovated private 1-bedroom cottage, walking distance to Kailua Beach and Town. With a private yard a lusciously landscaped garden with outdoor dining & BBQ. ...
    Registration Number: GE-121-728-3584-01, 43071011, TA-121-728-3584-01, 143071110000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua
    14  reviews
    from $513 
      View Property   Book Now

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