We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Beach Rentals and Condos in Kailua, HI

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $628 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Kailua are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 23
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 24
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    5 of 5 bubbles (8) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 13
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Shared Yard
    • Wi-Fi
    • Outdoor Dining Area
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Kailua, Oahu 96734
    1 / 15
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Parking
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with microwave, hot plate, toaster... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed August 6, 2016
    We had a wonderful time at Simone's place. The apartment is very spacious and clean, the ocean really is just a couple of steps away. Simone and her kids are great hosts and were...
    5 of 5 bubbles Reviewed August 3, 2016
    We are in our 70's... but active... and found Simone and her family and the rental to be perfect for us. It's a 5 minute or less walk to the beach and within walking distance from...
    See all reviews
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 24
    5 of 5 bubbles (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed September 11, 2016
    We have been to Oahu before and it is rare to find such a modern/ updated place to stay. It was clean and so convenient. We had enough toiletries, bath towels etc. for our 3 night...
    See all reviews
    1 / 12
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Secure Parking
    • Terrace
    • Mountain Views
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Lovely Guest House with lots of upgrades<BR><BR>Large Bathroom with paintings of Lanikai Beach<BR><BR>California King Bed and 60inch Flat-Screen TV<BR><BR>Super Fast High-Speed Internet up to 60MB/s with WiFi Access<BR><BR>Full Kitchen with top of the line appliances <BR><BR>Washer and... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed April 16, 2016
    Private, near the beautiful beach but also close enough to town and shopping, restaurants, etc. The property shows pride of ownership and has most amenities you will need...
    5 of 5 bubbles Reviewed October 3, 2015
    Wonderful immaculate, quiet, spotlessly clean, idyllic guest bungalow with charming porch and grassy front yard. Walk to Kailua Beach, Kiteboarding, Restaurants, Bike Rental, and...
    See all reviews
    1 / 34
    5 of 5 bubbles (12) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Satellite TV
    • Parking
    • Washer
    • Internet Access
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed July 7, 2016
    We had a wonderful stay at Suite Aloha. The suite is impeccably clean with cute and tasteful island decor. It is also stocked with everything you would want for a stay at the...
    5 of 5 bubbles Reviewed February 14, 2016
    My husband and I stayed here for 6 days while in Oahu and we were very pleased with the accommodations. The owners were very friendly and we were treated like friends instead of...
    See all reviews
    1 / 30
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Private Outdoor...
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 4 weeks ago
    The house was beautiful and the pool was an added delight. It was a great place for 7 adults. My only complaint was that the mattress in the master bedroom was so bad I had to...
    3 of 5 bubbles Reviewed May 21, 2016
    Try to arrive during daylight as the lane/driveway to access the rental is a bit tricky. We arrived very late but once we located it we had east access via key in locked...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 2 weeks ago
    ''High up in the hill'' overlooking the nice Lanekai beach, giving a fresh breeze and the nice sound of the waves on the reefs. It is recommended to have a car. The driveway might...
    See all reviews
    1 / 28
    5 of 5 bubbles (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 bubbles 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 bubbles 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...
    See all reviews
    1 / 7
    4 of 5 bubbles (1) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The Ginger Studio has free off... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed January 30, 2014
    We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
    See all reviews
    1 / 21
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. <BR>Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed March 11, 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would be...
    5 of 5 bubbles Reviewed July 21, 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
    See all reviews
    1 / 17
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Shared Yard
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Washer
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 15
    5 of 5 bubbles (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles 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 bubbles 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...
    See all reviews
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    1 / 13
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • DVD Player
    • Satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed April 9, 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
    5 of 5 bubbles Reviewed March 23, 2016
    While this property only rents for a month at a time, it was a great retreat from the world. With private beach access to a wide sandy beach and the wind in the palm trees, you...
    See all reviews
    1 / 15
    4.5 of 5 bubbles (35) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Wi-Fi
    • Patio
    • Satellite TV
    • Shared Yard
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach.<BR><BR>With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed September 3, 2016
    If you choose Hawaii, you have to choose Tina's studio. No wonder celebrities have their vacation at Kailua. The apartment is perfect and the lush garden makes both inside and...
    4 of 5 bubbles Reviewed May 29, 2016
    The place is in a very good location, you can walk to cafes and restaurants, or the beach. The studio apartment is very nice, with a good bed. We slept very well. But here is one...
    See all reviews
    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool...
    • Private Yard
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Get the List
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The majestically beautiful Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home.<BR><BR>Tranquil, and safe, this home is in a quiet residential... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    • Housekeeping...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 22
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Washer
    • Mountain Views
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Completely Renovated Cottage in Kailua in very close walking distance to the beach.<BR>High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub.<BR>Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed.<BR>Our... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed April 12, 2016
    This is an excellent rental if you're looking for a place away from the resorts and tourists. Great location with a 5 minute walk to the best beach on Oahu. Plenty of...
    See all reviews
    1 / 22
    4.5 of 5 bubbles (19) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Secure Parking
    • Wi-Fi
    • Grill
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed July 13, 2016
    If you're looking for 5 star accomodation, this is not the place for you, however if you want a place to stay that's comfortable in a convenient location, then this will suit you...
    5 of 5 bubbles Reviewed May 14, 2016
    This house was everything we saw online. The managers went out of their way to provide us with a VitaMix to make our morning smoothies. We thought there would be bicycles...
    See all reviews
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lovely hideaway two bedrooms are attached " Ohana" to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 10
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Washer
    • Private Yard
    • Grill
    • DVD Player
    • Wi-Fi
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    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 bubbles 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...
    See all reviews
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Patio
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua. The property is secluded with a... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 8
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy Orchid studio in private home. Private entrance and bathroom. Three blocks from the beach. Air-conditioning and ceiling fan. Small covered patio with table & 2 chairs. Small light meal prep. area. Small Refrig, microwave, toaster, coffee maker, hotplate. Pots, utensils, dishes. Linens,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Terrace
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 / 6
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    1 / 8
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 14
    4.5 of 5 bubbles (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Air Conditioning
    • Secure Parking
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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 bubbles 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...
    See all reviews
    1 / 7
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Patio
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Outdoor Dining Area
    • Private Yard
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Kailua, Oahu 96734
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Washer
    • Mountain Views
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Enjoy the island lifestyle at beautiful Mokulua Cottage, situated on beachfront property-just steps from the sand! This incredibly spacious two bedroom/one bathroom home is perfectly suited for your island getaway. A full renovation was recently completed in February 2016 with many upgrades... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Satellite TV
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Over the canal, past the boat ramp and round the bend is where you’ll find the Ocean’s Edge in Lanikai. Just a walk on the beach, afternoon swim or bike ride away! This 5 bedroom, 3.5 bath oceanfront home is set dramatically close to and slightly above the ocean’s edge. The living room’s picture... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This exquisitely furnished apartment is located in one of Kailua's most coveted neighborhoods on a ridge overlooking Kailua Beach. Watch the surfers on Flat Island as you enjoy breakfast on your beautiful lanai. Between the views, the exquisite furnishings and the generous closets with built-ins,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 10
    5 of 5 bubbles (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Balcony
    • Grill
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed October 20, 2014
    This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
    5 of 5 bubbles Reviewed March 10, 2014
    I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
    See all reviews
    1 / 33
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Mountain Views
    • Washer
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Experience true island living in this stunning historic beachfront residence on the white sandy shores of Lanikai. Hale Hinano is one of the original mansions built on the best part of Lanikai Beach in the 1940's, and has been beautifully renovated with extensive upgrades to become the luxurious... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 14
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Lets be honest... one of the main reasons you're visiting Hawaii is for the beautiful weather year round and the jaw dropping beaches. Our vacation rentals are all within walking distance to one of the worlds most beautiful beaches, Kailua beach. Two of our properties (our Awakea & Ali'i... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed February 26, 2016
    Nice place to stay!!!!! I stayed with my 15 years old son for about 10 days.. This studio was very confortable and very well ubicated, we walk around Kailua from the studio and...
    See all reviews
    1 / 37
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Grand Kailua Beachside Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 6
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed August 13, 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
    See all reviews
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5 minute drive to the beach. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy panoramic views of... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 21
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Kailua, Oahu 96734
    1 / 24
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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
    Kailua Vacation Rentals

    Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

    A Kailua Vacation

    Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

    Family-Friendly Kailua

    From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.