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Rentals for Seniors 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.
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    1 / 13
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 13
    5 of 5 stars (1) Excellent
    Private Room, 3 Bathrooms, Sleeps 3 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C in the bedroom. There is a... View all property information
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    Kailua, Oahu 96734
    1 / 10
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only 1-1/2 blocks to famous Kailua... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed January 6, 2015
    Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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    1 / 28
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed March 14, 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close to...
    5 of 5 stars Reviewed March 11, 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite... View all property information
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    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more... View all property information
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
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    About this property
    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
    Location Information
    Kailua, Oahu 96821
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Sandbar Cottage is an immaculate and beautifully appointed 2 bedroom / 2 bath unit located just a short stroll to one of the most beautiful beaches in the world, Kailua Beach. The unit is fully furnished with A/C in all rooms, cable TV, DVD player, Wi-Fi, washer/dryer, BBQ and access to beach... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 1 week ago
    The Sandbar Cottage in Kailua exceeded all of our expectations! The entire cottage was warm, inviting and family friendly while at the same time elegant, lush and private, with a...
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    1 / 8
    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    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
    1 / 26
    5 of 5 stars (23) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    About this property
    This gorgeous, beautifully furnished Ocean View home is a stone's throw from Kailua Beach and sleeps up to 8 comfortably. There is a large, sparkling, fully tiled swimming pool, 2 jacuzzi tubs, central air conditioning, 3 large bedrooms with ocean views, and 4 baths. Dolphin Manor is an... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed March 13, 2016
    We loved the house. Big enough for everyone to have their own room and bathroom. Dining area to accommodate our family. The pool was our grandson's favorite part. We enjoyed the...
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    1 / 24
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • DVD Player
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    • Mountain Views
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    • Hot Tub
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    • x
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    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
    5 of 5 stars Reviewed July 4, 2012
    Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • x
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    • ?
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed January 10, 2014
    Lots & lots of room. Family of 7 - 2 kids (8&10), 2 couples & single. So there was plenty of space that we could stay out of each others hair and off each others nerves. We...
    5 of 5 stars Reviewed December 19, 2013
    Our family of four, my friends family of 5 and my Mom and step father stayed here for 10days. I would recommend it. the beds were comfortable, as was the house. There was no air...
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    1 / 15
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed May 10, 2016
    Nancy's Cottage was better than we expected, it was new, clean and had all the amenities we needed for our stay. It was also perfectly located, close to the beach and shops. There...
    5 of 5 stars Reviewed August 12, 2015
    Rick and Nancy's cottage is lovely on the inside, newly renovated, perfectly clean, well stocked, w an incredibly comfortable bed. I have back issues and this bed is as comfy as...
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Peaceful, quiet and gated entry. 10 min. to Kona town & uncrowded pristine beaches 15 min. to beautiful Mahai'ula Beach 5 Min To Keahole Airport & Makalei Golf Course 1 bedroom guest units with large baths & full kitchens. Our guest units are on 4 acres over looking the Kona Coast, on the... View all property information
    Location Information
    Kailua, Oahu 96740
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This home located can accommodate up to 12 people comfortably and can also be split in half to accommodate smaller parties. Located directly across the street from the Kailua Beach Park and Boat Launch, this modern rebuilt two-story home has a front main house consisting of 4 bedrooms, 4... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 13
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • x
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    • ?
    About this property
    Studio with private bath, private entrance and kitchenette, close to Kailua Beach Park and Kailua town. The 240 sq foot Studio features a queen bed, pull out sofa bed, table and chairs, ceiling fan, TV, AC and High speed internet access. Pool on property. The kitchenette counter is equipped with a... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed May 6, 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a grill...
    5 of 5 stars Reviewed February 16, 2016
    We have stayed in the Garden Studio 3 times. We loved it so much we kept coming back. Excellent location, a five minute walk one direction takes you to beautiful Kailua Beach...
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    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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
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    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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
    Location Information
    Kailua, Oahu 96734
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Coral Room seaside studio Tax ID 7873026-01 Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard with barbecue. Located in the best neighborhood in Kailua, enjoy the sounds of the ocean and feel the tropical trade winds.Has... View all property information
    Location Information
    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    You will enjoy your one bedroom, king size bed, and fully furnished kitchen. Beautiful full service resort with a beautiful beach. Your ocean view room gives you views of Molokai Island. Watch the surfers, outriggers, kite surfing from your large balcony. Two world class golf courses close by. The... View all property information
    Location Information
    Kailua, Oahu 96761
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Mountain Views
    • Patio
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    • x
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    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96744
    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