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Beach Rentals and Condos in Kailua, HI

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    Travelers to Kailua are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 15
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 stars (23) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This multi-million dollar Beachfront home has over 3,100 spacious square feet of living space. The 6 bedrooms and 5 baths (plus a dry heat sauna) surround the large courtyard and pool creating a very unique and private layout. This home is the perfect gathering place for friends and family to enjoy... View all property information
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    Kailua, Oahu
    1 / 10
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
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    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you... View all property information
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    Kailua, Oahu 96821
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the... View all property information
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    Kailua, Oahu 96734
    1 / 24
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
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    Kailua, Oahu 96734
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air... View all property information
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    Kailua, Oahu 96734
    1 / 8
    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. <BR><BR>Complimentary assigned parking on property and laundry... View all property information
    Location Information
    Kailua, Oahu 96734 6734
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    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    This executive beachfront home is right on Kailua Beach. Decorated with island-style rattan furnishings, ceiling fans throughout, cool white tile, and wood flooring. Central air conditioning, wonderful ocean views are just a few of the amenities. The gourmet kitchen comes with granite accents... View all property information
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    Kailua, Oahu 96734
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Walk to the most beautiful beach on Oahu. Great for large groups up to 12 guests. Koolau Mountain view from upstairs Lanai. The Plumeria Cottage is upstairs has 3 bedrooms, 2 baths and a full kitchen. It has a partial covered 400 sq ft lanai with mountain views. Perfect for relaxing outdoors.... View all property information
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    Kailua, Oahu 96734
    1 / 24
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu’s northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination. The grounds are covered in lush tropical flora with panoramic views of... View all property information
    Location Information
    Kailua, Oahu 96734
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Cozy "Ginger suite" studio in private home. Private entrance and bathroom. Three blocks from the beach. 1 block from the 57 bus stop. 3 blocks to shopping, restaurants and market. Air-conditioning and ceiling fan. Small covered patio. Little kitchenette for light meal prep. Small Refridg,... View all property information
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    Kailua, Oahu 96734
    1 / 12
    5 of 5 stars (34) Excellent
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Blossoms and palms welcome you as you enter the property. You are surrounded by shading trees and tropical flora. Just steps away is beautiful Lanikai Beach approximately 30 yards, just across the street. Lanikai is a quaint beachside community in Kailua on the island of Oahu.Our private,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can... View all property information
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    Kailua, Oahu 96734
    1 / 13
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 29
    4 of 5 stars (1) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Kailua Beach House is a casual, two-story 6 bedroom, 4.5 bath beachfront home with 5,000 square feet of living space. The 1/2 acre privacy-fenced property features a large, free-form swimming pool which has a poolside cabana with a shower and a built-in BBQ. The property decor features light... View all property information
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Cute Bungalow! 2 1/2 blocks from beautiful Kailua Beach. Cool AC. King size bed. Kitchenette for cooking with all you need to make meals and eat at home to save $ . Nestled in a private lane and just a 10 min walk to the beach. This is a stand alone unit, so you have the place to yourself. Our... View all property information
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    Kailua, Oahu 96734
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Kaimalino Kai is a two story, 3 bedroom, 3 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 elegant indoor and lush outdoor spaces. Live each moment of your relaxing... View all property information
    Location Information
    Kailua, Oahu 96734
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Stay like locals! Hotel in Waikiki doesn't excite you? Quiet and beautiful Kailua is the best option for you and your family! We offer a beautiful Hawaiian-theme guesthouse with spacious, 15 ft high-ceiling 2 bedroom, 1 bath with full kitchen where 4-5 people can sleep. One of the rooms have a... View all property information
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    Kailua, Oahu 96734
    1 / 42
    5 of 5 stars (14) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Hawaii GET and TAT ID# OII968I4-OI Our ohana (family) welcomes you to 'Kauhale' our beautiful Hawaiian home. We offer a large cool and breezy 1000 sq ft, 1 bedroom, 1 bath, private, 2nd floor apartment, includes all utilities, located in a great family neighborhood, vaulted open beam ceilings... View all property information
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    Kailua, Oahu 96734
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is... View all property information
    Location Information
    Kailua, Oahu 96734
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <BR>Ocean Front House, 2 Bdrm/2 Bath + Ohana Room, Sleeps 4-6. Great outdoor spaces.<BR><BR>Honu Hale Lanikai (Honu means turtle, Hale means house) is a simple and comfortable two bedroom oceanfront vacation home in beautiful Lanikai on the island of Oahu. It has one bedroom/one bath in the main... View all property information
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    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ** Please note that the owner of this home lives on the property, in an attached house with its own separate entrance. She's very friendly, but will be extremely respectful of your privacy. She will also serve as your own personal local contact, making it easy to assist you with any questions or... View all property information
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    Kailua, Oahu 96734
    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
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    Kailua, Oahu 96734
    1 / 32
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    The Paradise Point Estate is a rare jewel that comes fully appointed with Plantation style finishes and furnishings from around the world. Step from a secure entry and motor court into beachfront luxury that whispers old Hawaii, yet offers all of the latest amenities and technologies of a modern... View all property information
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    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    This sweet Ohana apartment is quaintly situated downstairs with it's own private entrance. If you are looking to find a quiet location away from loud downtown Waikiki this Lanikai Ohana is perfect. It has a bedroom and bathroom with a full kitchen, full size refrigerator, living room and charming... View all property information
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    Kailua, Oahu 96734
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Welcome to the world of John Walker. 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 Honolulu Hale (City Hall). Mr. Walker's inviting presence is felt in the... View all property information
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    Kailua, Oahu 96734
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    HONU HEAVEN TAT# W27612003-01 Just remodeled, beautiful vacation rental 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 privacy and manicured yard space, a... View all property information
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    Kailua, Oahu 96734
    1 / 40
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    BALI RESORT TAT# W-89407732-02 Relax in the lap of luxury at this exquisite beachfront estate totaling nearly 60,000 sq ft. Spend lazy mornings strolling along the gorgeous stretch of the world-renowned Kailua Beach and sleepy afternoons relaxing beside the resort style pool with its bubbling... View all property information
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    Kailua, Oahu 96734
    1 / 24
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    BEAUTIFUL BEACHFRONT 1 bedroom 1 bath suite for 2 adults, or the whole 2 bedroom 2 baths for 4 guests. Tropical paradise directly on Kailua beach! This fabulous home is tucked away at the end of a quiet and private beach side lane. Designed with many giant windows and oversized sliding glass... View all property information
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    Kailua, Oahu 96734
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can be divided into three separate living quarters when you need privacy. This home is all on one level and... View all property information
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    Kailua, Oahu 96744
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    After a day of sightseeing or hanging out at the beach, my home welcomes you back with Hawaiian hospitality. Before the evening activities, you might want to take a short nap out back in the hammock, catch up on the latest news on the 47' TV or with the free WiFi, or grill some fresh Hawaiian... View all property information
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    Kailua, Oahu 96734
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The... View all property information
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    Kailua, Oahu
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five bedrooms, including one guest... View all property information
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    Kailua, Oahu 96734
    1 / 44
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The Essence of Kailua Beach Living Castle Point Estateis an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it’s new... View all property information
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    Kailua, Oahu 96734
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    SANDCASTLE TAT# W00099504-01 Peaceful beach house with stunning oceanviews on world famous Kailua beach! With white sands and clear shallow waters right outside the door, comfortable, spacious living for the whole family inside, and a beautiful pool with waterfalls, Sandcastle offers an ultimate... View all property information
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    Kailua, Oahu 96734
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • x
    About this property
    Beautiful 1-5 bedrooms private vacation rental units on #1 rated Kailua/Lanikai beach. Just 18 minutes away from Honolulu airport and Waikiki hotels. These surrounded by tropical gardens luxurious villas offer 2 studios, 3 bedrooms condo or a 5 bedrooms house. If you are planning dream vacations... View all property information
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    Kailua, Oahu 96734
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#W-30525774-01. This comfortable family vacation rental home on a beautiful sandy beach is the perfect antidote to civilization. Waters protected by... View all property information
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    Kailua, Oahu 96734
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This Hawaiian style home is a perfect peaceful getaway for you and your extended family. It's just steps from one of the most beautiful tourist-free beaches on the island of Oahu. Listen to the waves crashing as you relax on the lanai, or barbeque for your group in true outdoor Hawaiian fashion.... View all property information
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    Kailua, Oahu 96734
    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This European tropical retreat home is located in one of the most convenient areas of Kailua, easy access to Waikiki, Honolulu, the airport and both Waimanalo and Kailua beaches. Executive house is fully furnished and has everything you will need. Beautiful mountain views as soon as you step out of... View all property information
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    Kailua, Oahu 96734
    1 / 37
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
    Location Information
    Kailua, Oahu 96734
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two Bedroom Premium Lockoff Villa An experience in rejuvenation, the 1,311-square-foot, two-bedroom, two-bath deluxe lockoff villa comfortably sleeps eight while providing every amenity necessary for your idyllic retreat in paradise. The two bedroom villa is your personal retreat with 1,311... View all property information
    Location Information
    Kailua, Oahu 96722
    1 / 21
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    We have 2 properties located directly across the street from one another with two 1 bedroom/ 1 bathroom units between the two properties as well as a two spacious studios & 4 private rooms. All our units have their own private entrances and outside sitting areas. Both these properties are centrally... View all property information
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    Kailua, Oahu 96734
    1 / 34
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Patio
    • Hot Tub
    • Waterfront
    • Satellite TV
    • DVD Player
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    HALE HIKINA TAT# W17314247-01 Ensconce yourself in unpretentious luxury at Hale Hikina, where the indoors flow seamlessly into the outdoors with kingly travertine marble floors and exquisite custom furnishing. Enjoy soft sands, the warm embrace of the Pacific, cooling trade winds, and endless... View all property information
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
    Location Information
    Kailua, Oahu 96734
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Plumeria, avocado, and mango trees surrounded by red and pink ginger; red, pink, white, and yellow hibiscus; orchid; heliconia; anthurium, and many more tropical plants enclosed by rocks walls, fencing, and an 8 foot hedge to create a private tropical paradise. The sounds of the small waterfall... View all property information
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    Kailua, Oahu 96734
    1 / 23
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    HALE MAHINA TAT# W51388984-01 Stunning Island Style with large covered lanai area. Perfect indoor outdoor living with private pool to relax and enjoy! Walk across the street to Kailua's white sand beach! Bright open floor plan. Professionally landscaped, fenced yard, central a/c, Main home has 4... View all property information
    Location Information
    Kailua, Oahu 96734
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    About this property
    In the middle of the great Pacific, on the world’s most isolated chain of island, lies a small coastal community that is blessed with heaven-like beauty. LANIKAI, the “heavenly sea”. The envy of all paradises. It’s crystal clear waters, white sand beaches and lapping shores offer a warm... View all property information
    Location Information
    Kailua, Oahu 00000