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Holiday Rentals near Kiholo Bay

Mile Marker 81 on Hwy. 19, Kailua-Kona, Island of Hawaii, Hawaii 96740
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    Travellers to Kailua-Kona are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 28 Rentals in Kailua-Kona
    1.5 kilometres from Kiholo Bay
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    OceanView Plumeria Suite, kitchenette,Sprechen Deutsch. Bears' Place Guest House1 / 22
    (50)Excellent
    7.0 kilometres from Kiholo Bay
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Brown Turtle House1 / 24
    (3)Excellent
    7.8 kilometres from Kiholo Bay
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    7.0 kilometres from Kiholo Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Terrace
    • Mountain Views
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely GINGER ROOM is one of 5 studios at BEARS' PLACE GUEST HOUSE in Kailua Kona. Our guest house is a great home-base for exploring the Big Island of Hawaii. We are located on the hillside, overlooking the Kona Coast, 7 miles north of downtown Kailua, at a comfortable elevation of 1,600'; so...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2.5 kilometres from Kiholo Bay
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate....
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1.9 kilometres from Kiholo Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fabulous property in the exclusive resort community of Four Seasons Resort Hualalai is perfect for both families and couples. Sweeping panoramic ocean and coastline views greet you as you walk through the front door of this well appointed upper level gem. Floor to ceiling glass pocket doors...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.2 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate....
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.9 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate....
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.1 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate....
    View all property information
    Location Information
    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.9 kilometres from Kiholo Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for families & couples alike, this luxury property is situated in the award winning resort community of Four Seasons Resort Hualalai. Sweeping panoramic ocean views and gorgeous natural light greet you as you walk through the front door. Receding glass pocket doors open from the living area...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.7 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate....
    View all property information
    Location Information
    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.9 kilometres from Kiholo Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Luxury Two Bedroom Suites, Ocean Views with Lanai & Yard This Time... Stay In A Villa. Guests love the experience of this luxury, ocean-view Villa within the Hualalai Resort. The Villa is decorator-furnished with separate bedroom suites, each with a full bath. The Owner's Suite also features a...
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    Kailua-Kona, Island of Hawaii
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.2 kilometres from Kiholo Bay
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Internet Access
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent island-inspired, custom Hawaii luxury vacation rental home features over 6,300 sq. ft. of elegant living space with four bedrooms-each complete with separate garden outdoor shower lanais-as well as a fifth bedroom in an intimate guest house. Five Star Resort Access at Four Seasons...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3.2 kilometres from Kiholo Bay
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our exquisite 4 bedroom, 4.5 bath resort home cradles its guests in the lap of sumptuous serenity. Situated on a premiere private corner lot overlooking the 13th green of the exclusive Ke‘olu golf course, this home boasts over 4,200 square feet of interior living space and 1,500 square feet of...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2.8 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the 4th fairway of the Hualālai Golf Course, this 3 bedroom townhome offers stunning expansive vistas from both upper and lower levels including the Pacific Ocean, Maui, and the Hualālai Mountains. Equipped with modern conveniences and decked out in style, this villa is perfect for a...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    7.0 kilometres from Kiholo Bay
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Balcony
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful top floor ocean view ORCHID SUITE is one of 5 lovely studios at BEARS' PLACE GUEST HOUSE in Kailua Kona. Our guest house is a great home-base for exploring the Big Island of Hawaii. We are located on the hillside, overlooking the Kona Coast, 7 miles north of downtown Kailua, at a...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3.0 kilometres from Kiholo Bay
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the spectacular Kona-Kohala coast sits the incredible Hualalai Resort. With its dramatic white sand beaches, dazzling oceanfront access and views, and black lava landscapes, visitors will have their senses and desires tantalized! Kai Malino Estate 147 sits in the heart of this favorite...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2.0 kilometres from Kiholo Bay
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Four (4) bedrooms and four (4) and one-half bathrooms in approximately 5,000 square feet including interior space and covered lanais . - Fully furnished with tasteful furniture and artwork - Beautiful ocean views overlooking hole #1 of the Tom Weiskopf signature Keolu golf course - Master Bedroom...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2.9 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning villa is part of the world-class Hualalai Resort on Hawaii's Big Island. Situated at the entrance to Pakui Street, the villa is within walking distance of the beach at the Four Seasons, and enjoys easy access to the resort's championship golf course, spa, and other superb features....
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.9 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning villa is part of the world-class Hualalai Resort on Hawaii's Big Island. Situated at the entrance to Pakui Street, the villa is within walking distance of the beach at the Four Seasons, and enjoys easy access to the resort's championship golf course, spa, and other superb features....
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    Location Information
    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    7.0 kilometres from Kiholo Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Terrace
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely, tiled garden view HIBISCUS STUDIO is one of 5 lovely studios at BEARS' PLACE GUEST HOUSE in Kailua Kona. Our guest house is a great home-base for exploring the Big Island of Hawaii. We are located on the hillside, overlooking the Kona Coast, 7 miles north of downtown Kailua, at a...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3.4 kilometres from Kiholo Bay
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located within the Four Seasons Hualalai Resort, this corner lot luxury villa overlooks the thirteenth hole of their prized, Ke’olu Golf Course. With privacy, provided by lush palm trees, this Hawaiian home features four beautiful bedrooms, an open-concept layout, and plenty of outdoor social...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    7.0 kilometres from Kiholo Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Washer
    • Terrace
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely, garden view HELICONIA STUDIO is one of 5 lovely accommodations at BEARS' PLACE GUEST HOUSE in Kailua Kona. Our guest house is a great home-base for exploring the Big Island of Hawaii. We are located on the hillside, overlooking the Kona Coast, 7 miles north of downtown Kailua, at a...
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    Location Information
    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1.8 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you ready to recharge, refresh and indulge in luxury in the tropics? Our amazing last minute special can help make your dreams of Hawaiian sunshine come true. Availability will not last long - book quickly and give yourself the gift of paradise! Published pricing reflects the discounted rate.​...
    View all property information
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.1 kilometres from Kiholo Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're a family on holiday or a couple on honeymoon, you'll find plenty to love about the Hainoa Villa 2907B at the Four Seasons Resort Hualalai. This Big Island vacation rental pairs sweeping ocean views and the luxury of a private residence with access to the resort's amenities and a...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.6 kilometres from Kiholo Bay
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high ceilings, professional interior design, and a...
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    Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3.1 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 10-minute drive to Kona International Airport., Kai Malino Estates 147 is a beautiful three bedroom three bathroom home in the Award Winning Resort Community of the Hualalai Four Seasons. With gorgeous ocean views, the home is located on #9 of the Nicklaus golf course and is equipped with two...
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    Waikoloa, Kohala Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.2 kilometres from Kiholo Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether the aloha spirit or the golf course is calling your name, answer them at Kai Malino Estate 147. Part of the exclusive Hualalai Resort on the Big Island of Hawaii, this luxury vacation rental looks over the ninth fairway of the Jack Nicklaus course to the blue waters of the Pacific Ocean....
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    Waikoloa, Kohala Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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