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Holiday Rentals in Kailua-Kona, HI

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    ₹ 14,385 Average
    ₹ 67,000+
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    Travellers to Kailua-Kona are booking October dates now. Secure your holiday home today, and have the perfect trip.
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    4 of 5 bubbles (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lovely Oceanfront upgraded second floor 2bd2bth unit in Kona Bali Kai one of Kona's most popular oceanfront destinations. Watch the surfers at 'Banyans' from your lanai at one of Kona's premier surfing spots. Light, Bright, and Airy with several upgrades including new white paint, Hawaiian style... View all property information
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    Kailua-Kona, Island of Hawaii 96740
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Na Hale O Keauhou is a newer complex of townhomes located just 6 miles South of Kona. Our unit is at the quiet Northern end of the complex that overlooks a protected preservation area with unencumbered panoramic white water ocean views and beyond. No looking over or into another unit or them back... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    PRIVATE EXTERIOR ENTRANCE to this exquisite, 1BR suite. 500 sq/ft of clean, luxurious comfort. Gorgeous gardens. Insightful, onsite owners make it special, pointing you to great farmer's markets, art, food, beaches, snorkeling, culture, and more. There is a difference in Kona lodgings--we are... View all property information
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    Kailua-Kona, Island of Hawaii 96740
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    In town yet tucked away older hawaiian home its a simple place with a hawaiian touch , not a condo or hotel The quiet area and the view at about 1000 feet over looking the ocean Dolphins SPOTTED..... HAD A MAKE OVER BIG OCEAN VIEW Dolphins Spotted and Swam With I swam with the... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Sea Village Resort sits right on the sea wall. Located on prestigious Alii Drive. The well kept grounds surround a newly renovated pool, spa, barbeque and tennis court. Walk to town for a morning cup of the famous Kona coffee, shopping and evening ocean front dining. Big Island activities include... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Aloha and Mahalo for visiting our Home away from home vacation rental sight. Our 3 bedroom 3 bathrooms is a great vacation rental for larger families that have a hard time finding the place big enough for the whole family (2 extra rooms upon request). This lovely tropical property is in downtown... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Kona Isle is a beautiful oceanfront condominium unit has been designed with tropical tastes in mind with comfortable furnishings and all the amenities to make your vacation relaxing & carefree. This 1 bedroom 1 bath unit is located on the top floor (third) for the most desirable views where you... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    1 / 44
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Nestled in an exclusive gated community you will find our private "villa by the sea" overlooking the charming village of Kona. The yard affords a private, peaceful sanctuary with water feature and exotic gardens. Panoramic ocean views span the horizon as far as your eyes will take you; this... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Formerly VRBO #578333. This property is now under new management. New photos are scheduled for the end of December and/or early January pending weather. Spacious, airy, and light, this tropical vacation getaway is one of the rare corner units with a 20 foot cathedral ceiling. It has a wraparound... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    4.5 of 5 bubbles (15) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This vintage Hawaiian beach house is nestled in a private gated community of Kona Bay Estates. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of being in another place in another time.All beds... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Light and airy home filled with artist's paintings. An incredible place for your special occasion. One bedroom, large living room, dining room, and kitchen with 2 story cupola and view of the ocean. Great sunset views from our 10 ft. lanai (patio). Your home away from home. Paintings in every room... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    If you have a large group or extended family this is the home for you. Hale Nui Ohana (Large family home) is a large 2 story home with panoramic ocean views. Both upper and lower areas have separate entrances. Main upper floor has a full kitchen, dining, and media area with large HD TV and sofa... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    WELCOME TO NEW BEAUTIFUL CASA B,#135! GARDEN Floor Condo, very inviting, spacious ocean side condominium, which include many quality upgrades. One of only 9 Deluxe condos in this complex. Living Room~ There is a clean, Open feeling to this deluxe 920 square foot condo. Living Room features a New... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    For a virtual tour of this property scroll down to the bottom of the text and click on the link. Watch the Dolphins frolic and the whales in season from your own private lanai where the soft ocean breezes and the gentle waves lapping against the shoreline will relax your mind and body. Kona Bay... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Gorgeous and Spacious Home in Kona Vistas with Pool. Location, Location, Location. We are close to everything, at a fantastic elevation for great breezes and a quiet setting. Go just a street or two lower and you loose the breeze, the view and the quiet. Go just a few streets higher and it's a... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Hale Maluhia Nestled near the top of the hill overlooking the ocean, this home is just a few minutes from Kailua Kona town center. Perched upon a knoll at the perfect elevation of 920’ above sea level, it remains true to the Hawaiian word “Iolani” (Heavenly Hawk), offering absolutely stunning... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
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    About this property
    Beautifully decorated, quiet home in the Kona Highlands. Away from 'resort style' living, this very local home is the ideal place to get a true flavor of living in Hawai'i. A house that dreams are made and realized. Located in the cooler elevations, it tends to be less muggy and hot. You can... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    My name is Allen, and my wife and I invite you to enjoy your Hawaii condo at the Royal Kahili, located on Alii drive close to everything on the Kona Coast. Before we moved to Hawaii, this was our Hawaii home for years. You can enjoy the following as we have done: Go shopping, enjoy the... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Views that go on forever with breathtaking sunsets every night fully complimenting this gorgeous luxury home. Open floor plan with vaulted ceilings and architectural design features everywhere you look. Large pocket doors slide away to open the interior out to a huge lanai and infinity pool. The... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Our tropical and tranquil 2 story townhouse has two bedrooms and two full bathrooms. Private parking is directly in front of our unit. You will have living-dining-kitchen-bathroom and lanai on the first floor. The kitchen is well equipped for a variety of meals from smoothies to gourmet dining.... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Casa#111 is an excellent ground floor unit, that's VERY spacious! Nearly 1300 square feet! Close to the pool for easy access. There are new owners who own the property! Wifi! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambiance with tropical gardens and the songs of the... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    SIX night minimum stay charge , you may stay for less - but pay for 6 nights Clean, quiet, private, non smoking , WIFI. gas BBQ. Perfect for travelers on a budget who want a comfortable, clean and safe place to stay that is a close drive to town and beaches. Perfect base for sightseeing. NOTE:... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This spectacular ground floor unit is completely renovated from top to bottom. The new owners have made breathtaking changes, that really showcase how a Vacation Rental should look like. The details put into this gem are absolutely remarkable. Any guest staying here will enjoy & appreciate this... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Its a simple older Hawaiian Home it has a Hawaiian retro theme to it its an alternative place to the sterile same old place that more commercial places offer its not a condo or a hotel we thought daily breakfast passes to the best restaurant would be a nice way to spoil our guests book with us and... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This PINEAPPLE ESCAPE has been completely remodeled for your enjoyment of an island escape. Chic, modern, fun and relaxing vibe in this condo is the best spot for you to have as a home base and relaxation destination on your visit to Kona on the Big Island. It's location is prime with super easy... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    High end home in desirable neighborhood with amazing landscaping and close to beaches, shopping and restaurants. Large Lanai with 180 degree sunset view 365 day's a year. 3 car garage. Very private Honu Pool Hale with barbeque and seating above pool surrounded by many fruit trees. Large Master... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    5 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    About this property
    Hale Lani (Heavenly Home) is one of the Big Island's nicest luxury vacation rentals. Boasting complete privacy, the ideal elevation, and spectacular views, the property is perfect for larger groups, family reunions, small weddings and other events. The 4,700SF home, with living room, gourmet... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    There is a 30-night minimum stay required at Alii Cove. You may stay fewer nights, but we must block off 30 nights for each reservation. Our condo has the perfect location in Kailua-Kona. You can walk to the heart of town in about five minutes or you can simply cross the street and catch a wave... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Casa 321 is a true gem in the Casa complex! Lovely remodel! Being on the top floor, you can overlook the beautiful grounds and ocean. Central AC, Wifi, Beach gear! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambiance with tropical gardens and the songs of the many... View all property information
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    Kailua-Kona, Island of Hawaii 96740
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Its a simple older Hawaiian Home it has a Hawaiian retro theme to it its an alternative place to the sterile same old place that more commercial places offer its not a condo or a hotel we thought daily breakfast passes to the best restaurant would be a nice way to spoil our guests book with us and... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    1 bedroom, full bath, queen bed, dining room w/table, kitchenette, full size frig., induction cook top, microwave, coffee grinder and maker for brewing the famous kona coffee, wifi, cable tv, off street parking, coin operated laundry, gazebo with bbq. It is between Kahalu'u Beach (snorkel beach)... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Relax in your luxurious studio where your backyard is the ocean. Beautiful oceanfront setting where the waves splash just outside your room. Your comfortable bed is less than 35 feet from the ocean. Enjoy the fabulous views in your own private tropical bungalow. Ohana studio guests have their own... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    $119 special for ALL OF DECEMBER! Book with us DIRECT to get special rate! Townhouse living at it's finest! 3 bedroom property at an AMAZING value. SLEEPS 8! New appliances, furniture, granite counter tops; TV in the living room & in all the bedrooms. There are 2 queen beds upstairs with a window... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Make this home your own beautiful resort with all the amenities at no extra charge. Wailele Hale in Hawaiian means waterfall. Your wailele at the pool will bring you and you family and friends hours of enjoyment and memories that will last a life time. The yard truly is paradise, with 30 palm... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This beautifully furnished 1 bedroom 1 bathroom unit has been completely renovated. Situated on the ground floor, it leads to easy access to the property grounds and the ocean. Relax on the spacious lanai while taking in the sights of the great Pacific Ocean. The tropical décor is comfortable and... View all property information
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    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Located in a very desirable neighborhood, the Keauhou subdivision, this beautifully remodeled home sits right on the Kona Country Club Golf Course and offers exceptional golf course views! This home is surrounded by beauty and is directly across the street from beach/shoreline access, which leads... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • Patio
    • Balcony
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    • Private Outdoor...
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    People call it the Blue Lagoon home. The official Hawaiian name for the home is 'Hale 'Olu Olu', 'The home of relax and comfort' which was recently given the name by Kahu Danny Akaka after a traditional Hawaiian house blessing was done for the home. The home is considered a great Hawaii beach... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Waterfront
    • Private Outdoor...
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    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Alii Point an oceanfront home located in one of the best locations along the Kona Coast, is tucked away on a point within an exclusive quiet gated community. Within this gated community with fewer than 20 homes, you will find a pool, a tennis court, and a small private beach for your holiday... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    STUDIO CONDO - Sleeps 4 -FULL SIZE Everything in a COMPACT Space, INDUCTION BUILT-IN COOKTOP, Full Size Fridge With Ice Maker, Microwave/Convention, Murphy Bed, Sofabed, FLAT Screen TV Separate Vanity & Sink separated Toilet and Tiled Shower with pocket door. Comes Complete with linens, BEACH... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    3.5 of 5 bubbles (6) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This a Gorgeous almost ocean front unit with beautiful updated teak furnishing and updated appliances. There is everything you need to go the beach with the whole family snorkel gear, boogie boards, and umbrellas. It has a four post king bed with top of the line linens as well. This unit evoke the... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This well located complex is an easy walk to Keahou Shopping Center with a supermarket, Longs drugstore, movie theater and a variety of nice restaurants. You can walk to Keahou bay for paddling, snorkeling, kayaking or for the adventurous a night snorkel/dive to get up close with manta rays which... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Washer
    • Terrace
    • Grill
    • DVD Player
    • Balcony
    • Ocean Views
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Can't beat the price for this Wonderful spacious ocean view condo unit. A Home away from Home! White Sands Village is directly across from beautiful White Sands Beach (with its spectacularly clear water) on the Kona coastline - one of the few beaches in Kona! It is one of the few concrete... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Satellite TV
    • Grill
    • Internet Access
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    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Ironman special $2500 for up to 10 nights, all taxes and fees included, plus free parking, private, covered lanai to tune bikes, and free ride to pier on race day This lovely ohana (detached apartment) is in a very quiet and private, up scale gated community. At around 800' elevation, temperatures... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Imagine a warm, welcoming place where families and friends can feel a sense of peace, and share in the wonderment of seeing the blue Pacific Ocean stretch out, uninterrupted, from South to West to North. The pictures don’t lie: you have probably never been in a private home with views like these,... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Ocean Views
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Private comfortable home where your backyard is the ocean. Beautiful oceanfront home where the waves splash against your deck. Spectacular ocean views and gorgeous sunsets. The south side of our property is bordered by an ancient Hawaiian temple called the Ku'emanu Heiau that is dedicated to... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • Mountain Views
    • Grill
    • Ocean Views
    • Balcony
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Aloha and welcome to our home in Kona. This unit is new to the vacation rental market so we are offering it at introductory pricing until December. Check out the rates section. $105 for 2 people!!!! We have 5 star reviews at our other unit at Kona Isle and we want you to come visit, be happy with... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nice clean newly furnished second floor unit with central A/C. Great in town location right on Alii Drive. Walk to shops, restaurants & ocean activities. High speed internet access. Handicap accessable. Hawaii State ID # GE-*******-5312-01 Additional amenities include: coffee maker, nearby bank,... View all property information
    Location Information
    Kailua-Kona, Island of Hawaii 96740