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.

  • 1 Block to Kailua Beach Park/Private Patio/Blue Water Haven/washer/dryer/WIFI

    Enjoy the beauty and privacy of your own shaded, tropical patio or walk one block to Kailua Beach Park with its lawns, trees, and three-mile, white-sand beach. It is an easy walk to Lanikai Beach which Conde Nast Magazine has called the number one...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    145 USD - 145 USD

    nightly

    910 USD - 910 USD

    weekly

    3,600 USD - 3,600 USD

    monthly

  • NEW YEARS SPECIAL $120 p/nt Relax in Luxury & Privacy Kailua on a Gated Property

    Come stay at Hale `Awapuhi the house of red ginger. A luxurious, semi detached from the main home, large one bedroom apartment on the Windward side of Kailua. New for 2015, we just finished construction on a beautiful white fence and gate system s...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    145 USD - 145 USD

    nightly

    1,015 USD - 1,015 USD

    weekly

    3,900 USD - 3,900 USD

    monthly

  • Tax IDW14102399-01 Just A Short Walk To Kailua Beach

    Tax ID W14102399-01 Relax and unwind local style in our comfortable Island Breeze cottage. Just a short 5 minute walk and you can swim with the turtles in the crystal waters off kailua or Lanikai beaches. ...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    190 USD - 250 USD

    nightly

    1,750 USD - 1,750 USD

    weekly

  • AC, WIFI, KAILUA BEACH APARTMENT

    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

  • Nani's Cottage - 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

    325 USD - 525 USD

    nightly

    3,675 USD - 3,675 USD

    weekly

  • Beautiful Hawaiian Home on Cul de Sac with Gorgeous Kitchen, Bike to Beach

    E komo mai, welcome to our home in paradise. Our well equipped tropical home is located in the beach town of Kailua, world famous for it's white sandy beaches and bay. It's new on the market and is conveniently located less than a mile from bot...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    335 USD - 335 USD

    nightly

    2,345 USD - 2,345 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

    500 USD - 500 USD

    nightly

    2,800 USD - 3,500 USD

    weekly

    10,000 USD - 10,000 USD

    monthly

  • Beachfront! Newly Remodeled, Stylish Kailua Beach Home!

    TAT and GET license # W19195879-01 This four bedroom, three bath, Beachfront home has all new designer furnishings, and has been newly remodeled. The crisp white sofas, with beachy blues and greens mix well with the driftwood grey furnishings m...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    967 USD - 1,950 USD

    nightly

    8,813 USD - 8,813 USD

    weekly

    29,000 USD - 37,770 USD

    monthly

  • Kailuana Beachfront Estate-The BEST part of Kailua Beach - #1 in

    Spread on nearly an acre of prime Kailua beachfront, the two homes sleep 8-12 guests in a "main" house and detached guest cottage. This enchanting Kailua Estate is located in the premier part of the bay where the sand is at its widest and the turq...

    4 Bedrooms, 3 Bathrooms, Sleeps 12

    HI>Kailua

    7,000 USD - 17,500 USD

    weekly

    30,000 USD - 45,000 USD

    monthly

    1,000 USD - 1,500 USD

    nightly

  • Spectacular Kailua Beachfront Home - sleeps up to 14

    Casual accommodations located on Kailua Beach, voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit. Large outdoor deck spaces provide ...

    5 Bedrooms, 5 Bathrooms, Sleeps 14

    HI>Kailua

    9,800 USD - 24,500 USD

    weekly

    42,000 USD - 57,000 USD

    monthly

    1,400 USD - 1,400 USD

    nightly

  • Very Close To Kailua Town And Beach! Last minute discounted rates!

    The Maipele Hale is located on a Ohana (family) style property. The unit is on a second floor of the main home. This is a family friendly environment and we may even let your travel pet stay too! This 2 bedroom, 1 bathroom unit has everything...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

  • Truly A Beach House

    Charming beach house with the old kamaaina feel! This 3 bedroom, 3 bath house is one of the last around. This amazing property has it all. It is one of the few lots which offers the old hawaiian feel and sits on probably the most uncrowded white s...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

  • LAST MINUTE DISCOUNT- 10% OFF OR MORE- Ke'aloha Spectacular Beach-Side Getaway

    Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means "love," is certainly appropriate for this cottage. From the momen...

    4 Bedrooms, 2 Bathrooms, Sleeps 11

    HI>Kailua

  • Fabulous Luxury 6 Bedroom Kailua Beachfront-Private Pool and Spa

    Six bedrooms of beach-front paradise in Kailua. Swimming pool, Jacuzzi, game and TV room make this property an ideal vacation recreation destination. Three-quarter acre gated estate on Kailua Beach with pool, spa, beach vollyball and unobstructe...

    6 Bedrooms, 4 Bathrooms, Sleeps 12

    HI>Kailua

    17,500 USD - 21,000 USD

    weekly

    50,000 USD - 50,000 USD

    monthly

  • Spacious 1BR “Kailua Wave” Guesthouse, ½ Block to Kailua Beach

    LARGE, SPACIOUS and SECLUDED! 700+ square-foot one-bedroom guesthouse, located near the middle of the 5-mile stretch of gorgeous Kailua Beach. Private entry through keyed copper gates. Fully furnished with air-condition and beautifully decorated. ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Very close to Kailua beach and town!

    Our Kailana home is newly renovated and decorated with beautiful, comfortable, tropical taste. It is located in a wonderful beachside neighborhood in Kailua, Oahu. It takes a 6 minute leisurely walk to get to the beach. This property is large,...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Kailua Surf Studio. Love the Kailua Lifestyle.

    Live the Kailua Lifestyle. Listen to the surf from your 1 bedroom studio. Enjoy the quiet comfort of the Windward side's favorite small town - Kailua. Have your coffee on the beach each morning - Just a short walk. Private Studio (Ohana) w/ 1 ba...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Beachfront Luxury Private Boutique Villa

    East Lani in Oahu (Heavenly Gathering Place in Hawaiian) is your boutique, beachfront, resort-style experience. With a mile of exquisite beach in each direction, Oahu Lani is perfectly situated in the middle of pristine Kailua Bay, rated US No1 be...

    12 Bedrooms, 16 Bathrooms, Sleeps 60

    HI>Kailua

  • Premier Kailua Beachfront Getaway

    Theres a reason why Kailua is consistently voted as one of the top beach destinations in the world: its spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzzs Steak House and the quaint Hawaiian town ...

    6 Bedrooms, 5 Bathrooms, Sleeps 12

    HI>Kailua

  • Two Waters Retreat-A Fabulous Place To Stay In Kailua

    Welcome to Two Waters Retreat! This vacation getaway is close to the beach, hiking, shopping, dining, entertainment, public transport, and highway. You’ll love this place because of the desirable convenient location, authentic local Hawaiian livin...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Live Island Style in a Historic 1947 Hawaiian Style Redwood Home in Kailua town

    Vintage Hawaiian home, built in 1947 and completely renovated in 2006. We retaining the original charm and character, but updated and/or replaced the kitchen, the 2 bathrooms, all electrical, all plumbing, lighting, internet, and floors. This hou...

    3 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua

    2,800 USD - 2,800 USD

    weekly

    9,200 USD - 9,200 USD

    monthly

  • Enchanting Kailua Beach Bungalow - 100 Steps to Beach

    Aloha! We renovated this old-style Hawaiian home so that it will have the charm of old Hawaii with modern conveniences. The bungalow is on the ground level of a 2-story home. The 1/2 acre property is double gated (street side and beach side). It...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Two Bedrooms+Two Baths Walk to Kailua Beach Open: 3/30-4/4, 4/17-23, 4/30-5/8,

    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

  • Kailua Beach Cottage

    100% Kailua Lifestyle. 1 bedroom, 1 bath cottage with its own lanai. Enjoy the quiet comfort of the Windward side's favorite small town - Kailua. Have your coffee on the beach each morning - Just a short walk. One block to the beach - sunrise, sun...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Beautiful home, private pool, tropical garden, walk to beach

    Beautiful home with pool. Walking distance to Kailua Beach. Three bedrooms, one with a queen bed and a single bed, one with queen bed, one with a double bed. (Other bed configurations available on request.) Two bathrooms. Fully-equipped kitche...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

  • WINTER WHITE HOUSE; PLANTATION ESTATE; BEACHFRONT ON KAILUA BEACH, OAHU

    QUOTES FROM FORMER GUESTS: "My family and staff have grown very fond of our time at your home, and your generosity is much appreciated." President Barack Obama "Please make sure to name a suite after me! I shall return!" Charlie Sheen "Thank...

    5 Bedrooms, 5 Bathrooms, Sleeps 10

    HI>Kailua

  • Modern Kailua Beach Cottage

    Completely Renovated Cottage in Kailua in very close walking distance to Kailua beach (less than 2min) We are located right at Kalama Beach Park High Speed Internet with WiFi Access, 60inch- Flat-screen HD-TV, Oven, Microwave, Toaster, Coffee Mak...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Best Price and Location on Beautiful Kailua Beach!

    Modern, spacious, lovely studios and 2 bedroom accommodations, right on beautiful sandy Kailua Beach or only steps to top-rated Kailua Beach and the blue Pacific Ocean. Tropical yards surround these homes located in quiet, upscale neighborhoods. F...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Happy House on Exquisite Kailua Beachside Property!

    Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by stone walls with palms, banana trees and beautiful tropical gardens. Very safe and fun for kids, ...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

  • Steps To Kailua Beach! Large, breezy, comfortable! Last minute discounts!!!

    The Ocean Breeze Ohana unit is located beachside in Kailua. The location is incredible and just 50 steps to the beach. This is a large studio with the open living space with king size bed and fold out sofa bed. There is a fully equipped kitchen a...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Kailua Executive Estate Resort Living

    It is your home away from home. 4 bedrooms/ 4 baths/ Full Kitchen/ Living Room with 2 sitting rooms. Private Tennis Court and Swimming Pool. Beautiful landscaping on 2 and half acres. Views of Ocean and Mountains from most rooms. A bonus, a large...

    4 Bedrooms, 4 Bathrooms, Sleeps 10

    HI>Kailua

    9,765 USD - 10,465 USD

    weekly

    24,995 USD - 24,995 USD

    monthly

  • Beautiful Island Getaway ~ Kuu Home Uluwehi

    KU’U HOME ULUWEHI, 'My Verdant Home', Ku’u (To release, let go and welcome relaxation). Uluwehi (Verdant, green, lush and beautiful. A place where beautiful plants and guests thrive). This spacious home is a place of peace within a garden. Lo...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

  • 'Savannah's Cabana, Wireless Internet, Block to Kailua Beach!

    Great attention to detail was given to this separate cottage that was designed to match our Plantation-style home. The main house and this cottage share a beautiful tropical oasis that sits behind two houses offering peace and tranquility. Nestle...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Sweet Oceanside Beach Bungalow

    Aloha and welcome to Hale Roxi! Located on quite beach side street on two homes away from the beach.The beach at this spot on pristine Kailua bay offers the true Hawaiian getaway from crowds and noise.Recently fully remodeled in and out this home ...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

  • Beautiful Kauhale W/Sweeping Views of Kailua, 1.1 Mi To Beach all Taxes Included

    Hawaii GET and TAT Tax ID# W01196814-01 Our ohana (family) welcomes you to 'Kauhale Apartment' our beautiful Hawaiian home. We offer a lovely, very clean, large cool and breezy 1000 sq ft, 1 bedroom, 1 bath, private, 2nd floor apartment, vaulted ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

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