Kailua Vacation Rentals

Kailua is one of the most famous vacation rental destinations on Oahu, featuring a fantastic white-sand beach. Many of the vacation rental properties in Kailua are oceanfront, which makes Kailua the perfect destination for those looking for privacy or a romantic getaway. You can have your privacy here and in the same time enjoy easy access to shopping malls, restaurants and services. Kailua Beach is ideal for swimming, kayaking and windsurfing and was nominated the best beach in the U.S. by Condé Nast magazine in 1998.

  • Tropical Hide Away for Two

    If you're looking for a quiet getaway in residential Kailua just a few blocks from the ocean, here it is. Attached to our house is a remodeled one bedroom/bath with separate living room and small kitchenette to make your vacation a dream co...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    100 USD - 100 USD

    nightly

    700 USD - 700 USD

    weekly

    2,000 USD - 2,000 USD

    monthly

  • Comfortable BAY DRIVE COTTAGE, Close to Beach & Yacht Club

    This one bedroom cottage although attached to our residence, has its own separate entry through a lattice fenced/gated arbor and private patio garden. The parking area is accessed through a remote gate with a parking space right in front of the co...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kaneohe

    105 USD - 105 USD

    nightly

    693 USD - 693 USD

    weekly

    2,250 USD - 2,250 USD

    monthly

  • Swim with the Turtles - Cottage close to Kailua Beach Park and Lanikai

    The Palm Cottage is located on a secluded road, only a few short blocks from Kailua beach and minutes from Lanikai Beach. Nestled among tropical gardens, we have taken care to create a refuge of comfort that is designed to meet all your needs. A...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    125 USD - 125 USD

    nightly

    875 USD - 875 USD

    weekly

    3,350 USD - 3,350 USD

    monthly

  • New Quaint Kailua Cottage! Perfect Getaway Close To The Beach!

    Kailua Cottage is a 1 bedroom unit off the side of a beautiful home in Kailua. If you're looking for a clean, close to the beach, little oasis, this is it! This completely renovated 1 bedroom also has a full futon in the living room for additional...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    140 USD - 250 USD

    nightly

    1,225 USD - 1,225 USD

    weekly

  • As close as you can get to Kailua Beach

    Enjoy our Hawaiian sunshine and one of the most beatuiful beaches in the world. Our studio has high ceiling with a Monet- designed decor. A Large queen size 4 poster bed, with a sitting area and dining area. There is a breakfast bar which inclu...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    145 USD - 145 USD

    nightly

    1,015 USD - 1,015 USD

    weekly

  • Steps from Kailua Beach

    A lovely studio, newly built, only a minute or two from the beach (Kailua Beach Park) and Kalapawai market. Walk or ride bikes to kailua town (1mi. including whole foods, restaurants, and yoga classes), Lanikai beach and the pillbox hike (less th...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    147 USD - 147 USD

    nightly

    990 USD - 990 USD

    weekly

    3,000 USD - 3,000 USD

    monthly

  • Your Private Place in Paradise - Sleeps 2 to 4!

    The dramatic 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. Tranquil, and safe, this ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    148 USD - 160 USD

    nightly

    999 USD - 999 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Experience the Seabreeze in Kailua

    Enjoy a quiet, romantic, tropical vacation at 'The Seabreeze' located one block from award winning Kailua Beach. For best results, contact Carole or Grady at 808 261 0008, or 808 551 7486, or gradygeske@hawaii.rr.com, for preferred service. Our t...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    185 USD - 185 USD

    nightly

    1,295 USD - 1,295 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • Blue Ginger Cottage/Mele Hale

    Blue Ginger Cottage/Mele Hale - 'Happy Home' is situated in the wonderful town of Kailua on the windward side of Oahu. We are the owners living on the property, next to the attached cottage. We are available at your request to answer your questio...

    1 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    225 USD - 225 USD

    nightly

    1,575 USD - 1,575 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • KAILUA APARTMENT, AVAILABLE DECEMBER 1-31

    Charming upstairs vacation rental located in Kailua, just minutes from the World Famous Kailua Beach. This rental is decorated in Teak and Koa Wood furnishings, comes with a full kitchen, granite countertops, breakfast nook, air-conditioning, wir...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    225 USD - 350 USD

    nightly

    1,575 USD - 2,450 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches

    Lush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of keiki (children), this home was designed by the late Vladimir Ossipoff, award-winning Hawaii architect. Mr. Ossipoff's tr...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

    296 USD - 444 USD

    nightly

    1,851 USD - 3,047 USD

    weekly

    5,500 USD - 6,750 USD

    monthly

  • Entire, Spacious, Airy Family House - Minutes to Beach

    All the comforts of home await you at this perfect Hawaii getaway. The aroma of plumeria blossoms welcomes you. Designed by the dean of Hawaii residential architects, Vladimir Ossipoff, this large, open-plan home with a big, private back yard is a...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

    308 USD - 444 USD

    nightly

    2,023 USD - 3,047 USD

    weekly

  • Modern Beach House On Pristine Kailua Beach- In Town & Surrounded by Nature A/C

    The ultimate beach house! Modern and newly constructed, the Kailua Bay Beach House is nestled between the mountains and the beach. Located only 600 feet from the fantastic beach at Kailua Beach Park, the house overlooks the panorama of Kailua Bay ...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    400 USD - 600 USD

    nightly

    2,800 USD - 4,200 USD

    weekly

    10,000 USD - 10,000 USD

    monthly

  • Aloha from the Island of Oahu, and Welcome to Paradise!

    Aloha from the island of Oahu, and welcome to paradise! The Ko'olau Vista Villa is a large, private two-story, 4-bedroom (or 5-bedroom with bonus room), four-bath Island style 'open air' concept home located in beautiful Kailua, Hawaii. Known fo...

    5 Bedrooms, 4 Bathrooms, Sleeps 14

    HI>Kailua

    675 USD - 900 USD

    nightly

    6,300 USD - 6,300 USD

    weekly

  • Location, Location! Beachside, Just off the sand, Hawaiian Home with heated pool

    This incredibly charming traditional Hawaiian home is ideally located only one house back from the ocean in the heart of Kailua. A dream location, near Kailua Beach Park and walking distance to Island Snow and the famous Buzz's Steak house with wh...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    750 USD - 750 USD

    nightly

    5,250 USD - 5,250 USD

    weekly

  • Hawaiian Plantation Home Wrap Around Decks and Guest Cottage

    Great attention to detail was given to this 'Hawaiian Plantation -style' home that also has its own separate guest cottage. The main house has 4 bedrooms and the cottage has its own bedroom with a king size bed. Large expansive decks and lots of ...

    5 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    795 USD - 795 USD

    nightly

    20,000 USD - 20,000 USD

    monthly

  • 'Star of Hawaii' - OPEN DEC 1 - 26 - POOL, Hot Tub, Walk 3 houses to Beach

    You have found the 'Star of Hawaii' a residence on a private beachside lane. The home, gardens, pool and spa are encircled with lava rock walls. Relax around the pool or walk barefoot to the beach. Surrounded by tall palms and flowering plants, H...

    4 Bedrooms, 3 Bathrooms, Sleeps 12

    HI>Kailua

    835 USD - 1,250 USD

    nightly

    6,440 USD - 8,750 USD

    weekly

  • Tranquility Beachfront

    Enjoy sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand. This beautifully decorated 3 bedroom beachfront home pampers you with a large, well-appointed kitchen, upstairs master suite with soaking tub ...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

    850 USD - 1,350 USD

    nightly

    9,450 USD - 9,450 USD

    weekly

  • Kakela Kai - Beachfront Home, Kailua, Oahu, Private,Central A/C

    This is a well maintained beachfront home set in a security-gated neighborhood. It is decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile and wooden flooring. There is a gourmet kitchen with beautiful...

    4 Bedrooms, 0 Bathrooms, Sleeps 9

    HI>Kailua

    950 USD - 1,350 USD

    nightly

    9,450 USD - 9,450 USD

    weekly

    25,000 USD - 30,000 USD

    monthly

  • Beautiful Estate with plenty of room!!!

    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 a...

    6 Bedrooms, 4 Bathrooms, Sleeps 19

    HI>Kailua

    1,100 USD - 1,900 USD

    nightly

    7,700 USD - 7,700 USD

    weekly

  • 8 bd 4.5 ba Beachside Retreat - Steps from Kailua Beach

    Enjoy a great stay in this large house in the Kailua Beachside neighborhood, just 5 houses from Kailua Beach! The house features an indoor-outdoor floor plan with private courtyard & pool perfect for family entertaining! An extensive remodel incl...

    8 Bedrooms, 4 Bathrooms, Sleeps 16

    HI>Kailua

    1,100 USD - 2,200 USD

    nightly

    7,700 USD - 7,700 USD

    weekly

    25,000 USD - 35,000 USD

    monthly

  • 9 Bed/6 Bath, Close To Beach With Pool, With Ac And Tasteful Island Decor

    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 yo...

    9 Bedrooms, 5 Bathrooms, Sleeps 22

    HI>Kailua

    1,135 USD - 1,685 USD

    nightly

    7,945 USD - 9,100 USD

    weekly

  • Come To Paradise The Ultimate True Tropical Hawaiian Location!

    Paradise Bay is a beautiful waterfront resort community located on a rural peninsula just minutes away from Kailua and Kaneohe on the tropical Windward Coast of Oahu. We are less than a 30 minute drive to the Airport, Waikiki and North Shore and a...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kaneohe

  • Wonderful Little Cottage!!

    This brand new rental is now open. 2 Bedroom, 2 Bath cottage within a minute walk down the land to Kailua Beach. Perfect for a family of 4. This is a work in progress and more/better photos will be added shortly. *NOTE* - RATE QUOTE FROM VR...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua

  • Sandcastle - Peaceful Beach House ON THE BEST END OF KAILUA BEACH!

    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 wat...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    10,500 USD - 14,000 USD

    weekly

    31,500 USD - 42,000 USD

    monthly

  • Tropical Beach Hale, 1 bedroom, A/C, across street from beach access

    Aloha, come and relax at our tropical Kailua home located in one of Kailua's finest neighborhoods. Kailua Beach hale is located across the street from the beach access (300 feet to the access and about 700 feet to the waters edge) to a quiet sand...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    1,750 USD - 1,750 USD

    weekly

    4,200 USD - 4,200 USD

    monthly

  • Open: 1-2-7, 1/14-2/12, 2/23 on

    The Garden Suite and the Ginger Studio are under separate keys and yet... can be connected by an adjoining door. The Garden Suite, is larger one is a small one-bedroom suite. It has a private garden area with a magnificent white shower tree...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

  • Your Island Home Away from Home!

    Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the str...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

  • BEST LOCATION IN LANIKAI! Directly on the sand, come stay at HALE LANIKAI!

    Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#W-30525774-01. Leave your shoes in the suitcase and come enjoy barefoot living on Lanikai Beach! Greet e...

    4 Bedrooms, 4 Bathrooms, Sleeps 8

    HI>Kailua

  • Honu Heaven Is a GORGEOUS Oceanfront Home - Call or EMAIL FOR PROMOS

    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 w...

    4 Bedrooms, 3 Bathrooms, Sleeps 10

    HI>Kailua

    11,200 USD - 16,100 USD

    weekly

    33,600 USD - 48,300 USD

    monthly

  • The Perfect Kailua Retreat!

    You will feel Waioha ‘joy’ and happiness as you enter into your private tropical retreat. Waioha is a charming studio perfect for a single individual possibly touring or on a work exchange, or for a couple wanting to escape on a quiet vacation. ...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Gorgeous 'Green' Home on a Quiet Beach side Lane

    General Excise Tax Certificate: GE-108-567-9616-01 Transient Accommodations Certificate: TA-108-567-9616-01 Imagine living on a private lane just three houses from beautiful Kailua (Oahu) beach in a sparkling, spacious (3300 sq. ft.) fully equippe...

    5 Bedrooms, 2 Bathrooms, Sleeps 12

    HI>Kailua

    5,500 USD - 7,000 USD

    weekly

    16,000 USD - 24,000 USD

    monthly

  • $127/nt for A Month in Paradise! - 250 Steps to the Beach

    E komo mai to The Cottage at Hale Makai - our piece of island paradise in Kailua. Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu. Kailua Beach is routinely voted one of the bes...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Luxury Home-Steps to Kailua Beach-Heated Pool-Air Conditioned-Gated Entry

    This beautiful four bedroom, four bath, Hawaiian style home is just a short walk through Kailua Beach Park to pristine Kailua Beach. Newly constructed, this spacious, estate quality home is part of a private, gated community and offers serene Hawa...

    4 Bedrooms, 4 Bathrooms, Sleeps 8

    HI>Kailua

    4,865 USD - 5,250 USD

    weekly

    19,000 USD - 21,000 USD

    monthly

  • Private Executive Estate Waterfront W/ Pool in Kailua

    Welcome to Kailua Waterfront Estate (KWE). This private and gated executive home is perfect for your Hawaii vacation. Located in Kailua, Oahu, this clean, impeccably maintained home sits on an awesome corner lot with waterfront, golf course, and m...

    3 Bedrooms, 4 Bathrooms, Sleeps 6

    HI>Kailua

    2,555 USD - 4,550 USD

    weekly

    9,600 USD - 12,000 USD

    monthly

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