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Kailua-Kona Villas

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    Travellers to Kailua-Kona are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    35 Matching Rentals in Kailua-KonaView all 865 rentals
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    Oceanview Beach Villa, 2 bedroom, 2 bath, Sleeps 51 / 60
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Kona Hawaiian 2 Bedroom over looking the Bay w/ 2 pools and 2 hot tubs plus bbq1 / 11
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Kona Walk to Beach Spectacular Estate 6 Bed Pool1 / 15
    (6)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Reviewed 22 November 2015
    We had a delightful time! The owners were really good to work with, they were just a call away (except when Dana changed her phone number)lol. Some of the couples had to sleep...
    Reviewed 20 October 2014
    We came to Hawaii with 16 people, including 6 kids, and this house was perfect for us. It is laid out sort of like a little hotel with a common lanai & kitchen (each room...
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    About this property
    This wonderful beach house with private pool is perfect for all your vacation needs! Centrally located one short block from beach and walking distance to Magic Sands and Kahaluu Beach Park. 6 private bedrooms all with their own bathroom. The upper level has Three bedroom suites two with plush...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 18
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Parking
    • Grill
    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    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 96740
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    About this property
    Dramatic Golf and Ocean views, PLUS TWO Four-Seater GOLF CARTS Included One of the most luxurious villas at the resort with golf and ocean views and can easily accommodate up to 8 people comfortably.    The interiors of this villa will have you in the Aloha spirit in no time at Kaulu 129B.   This...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BREATH TAKING VIEWS  - This corner VILLA features 2700 sq. ft. of interior living space and another 500 sq.ft. of covered lanai that boasts unhindered views of the 15th hole Jack Nicklaus Signature Golf Course and OCEAN.  The villa comes with your own golf cart to whisk you to the resort and all...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Washer
    • Hot Tub
    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half bath, media room with 65” Smart TV, gourmet...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This exquisite villa is new to the rental market and perfect for sophisticated travelers. Whether vacationing with friends or family, this elegantly appointed upper level three bedroom will meet your needs and exceed your expectations!  Find your inner child as you cruise around the resort grounds...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of interior space, with impeccable décor by the...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Envelop yourself in the soothing sounds of the gentle waves on the shoreline as you relax and unwind in this exceptional ground floor unit - Hillside Villa 1102. Of the Hillside Villas, building 1100 has a direct view of the shoreline and is close enough to the ocean to hear the waves crashing on...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A design lover's dream, this 3 bedroom, 3.5 bath home is among the top tier of luxury villas at Hualalai.  The warm color palette and design features of this villa were inspired by a painting that hangs in the living area titled 'The End of a Perfect Day”.  The design team has used this painting to...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Tradewinds Villa! Tradewinds is set up with luxurious main house and guest house. The house has kempas hardwood floors, cherry cabinets in main kitchen, vaulted ceilings in spacious great room with large flat screen TV.  In the Guest house with 1 large suite and 1 smaller - both...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
    • DVD Player
    • Grill
    • Central Heating
    • Washer
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AVAILABLE: 12/1/18-12/8/18 When you stay at Wyndham Kona Hawaiian Resort in Kailua-Kona on the Big Island's west coast, you'll feel as if you're stepping back in time to a simpler, unspoiled era. Every detail has been designed to re-create the charming island ambiance found back in the '30s, while...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hualalai  Palm Villa130A ~3 bd~Stunning Sunset Views~Signature Garden Shower1 / 22
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a 'bonus' living room on the first level. The down-stairs suite opens to a large lanai and beautiful grass lawn to give...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Enjoy fabulous views of Mauna Kea to Maui ~ 2 bd~ Hualalai Fairway Villa 104D1 / 23
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 April 2014
    This 2nd floor condo/villa was perfect for our family of 4. It is much larger than the pictures make it appear. We priced out getting 2 rooms, a suite and a villa at the Four...
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    About this property
    Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are located within a short distance to the Hualalai...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hapuna Beach Villa is a 3000 sq. ft. one level luxury villa located in a secure gated community on the Hapuna Golf Course with 180 degree views of the ocean and Kohala mountains. The community includes a recreation center with large infinity pool/ spa, outdoor grills, indoor reading area and...
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    Kailua-Kona, Island of Hawaii 96743
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    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 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    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 96740
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    This exquisite villa is situated within a gated residential community at the Four Seasons Resort Hualalai, along the Kona-Kahala coast of Hawaii's Big Island. Designed by the esteemed Henderson Design Group, the 2,600-square-foot home blends beautiful décor, gorgeous ocean and golf course views,...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    This beautifully designed home is sited to capture panoramic ocean and sunset views. A private gated entry and tropically landscaped courtyard will lead you to both the main entrance and guest villa. The spectacular view is evident from the moment of entry.There you will find a recently refurbished...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The sun sparkles on the ocean, palm trees sway and the golf course beckons just outside Hillside Villa 7101. Set on the fairways of the Hualalai Golf Course, this Big Island vacation rental boasts a quintessential Hawaiian backdrop. Reserve its three bedrooms for a family holiday in the tropics, a...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Oceanview Kona Luxury Villa1 / 25
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The Ocean View Kona Villa is an amazing holiday destination on the Big Island. This was the PERFECT place for our extended family. We had a great time. Lovely and well cared for...
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    About this property
    The spectacular Kona Ocean View Villas are one of the Big Islands most luxurious, spacious and unique vacation properties on the Kona Coast. The Villas at the Kona Plantation gated community allow for single or multiple property usage with larger groups including family reunions, weddings and...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    This sensational villa is located within Hualalai Resort on the Big Island of Hawaii, an easy walk from the beachfront Four Seasons. Perhaps the finest property bordering the resort's golf course, the 6,300-square-foot home offers expansive outdoor living areas, spacious and elegant interiors, and...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    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 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    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 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hualalai Fairway Villa 116D - 3 bd villa with Beautiful Ocean & Golf Views1 / 25
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Internet Access
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on popular Waiulu Street just three minutes by golf cart to the Four Seasons Resort Hualalai, this large three bedroom single-level villa offers views of the 15th hole of the Hualalai Golf Course and ocean beyond. The villa is professionally designed and updated to include luxurious...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Private Garden
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    • 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 96740
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    This garden level 2 bedroom, 2 bath Fairway Villa overlooks the 15th Fairway of the Hualalai Golf Course with views of the ocean beyond. Located within the master-planned resort community of Hualalai, guests have the option of amenity use privileges at the Four Seasons Resort Hualalai, which is...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Hualalai Palm Villa is a spectacular three bedroom, three bath, two-story Hualalai villa on popular Waiulu Street at the world renowned Hualalai Resort. The Resort is home to the Four Seasons Hualalai, regarded by many as the #1 Resort in Hawaii. This exclusive Hualalai Villa is on the Four...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
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    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf course. Guests enjoy the extra space offered by the...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whale watch while listening to the breaking waves from the shoreline from the Master bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three bedrooms are en-suite. The two Master bedrooms have...
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    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hualalai Ke Alaula 210A ~3 bd~enjoy stunning ocean and sunset views1 / 25
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and shutter doors capture warm ocean breezes...
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    Location Information
    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hualalai  Waiulu Villa 137D~Single Level 3 Bd~Ocean, Punawai Pond & Golf View1 / 33
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of living space and a 414 square foot lanai with built-in...
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    Location Information
    Kailua-Kona, Island of Hawaii 96740
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
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