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Kailua-Kona Villas

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    Travellers to Kailua-Kona are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    36 Matching Rentals in Kailua-KonaView all 919 rentals
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    Oceanview Beach Villa, 2 bedroom, 2 bath, Sleeps 51 / 30
    (8)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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Ocean Views
    • Patio
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    • DVD Player
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Panoramic ocean views from living/dinning areas, kitchen and master bedrooms. Sitting on a knoll, guests at this villa enjoy gentle Hawaiian breeze as well as blue ocean views from the major rooms - living/dinning/kitchen /master bedroom /outdoor living rooms. 270 degree of tropical garden/lawn...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Kona Walk to Beach Spectacular Estate 6 Bed Pool1 / 30
    (6)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Reviewed 21 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 19 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 18
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    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Washer
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    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. Feel the aloha spirit at Hillside Villa 1102 Hualalai. Just a short walk or drive from the beach, golf, and downtown Kona, this vacation rental puts you close...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. 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...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Private Garden
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    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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    96743, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Spectacular Hualalai  Palm Villa 130A - Large Villa~Signature Garden Shower!1 / 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hualalai  Waiulu Villa 137D~Great Location~Punawai Pond, Golf and Ocean Views1 / 33
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. 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,...
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    96740, Kailua-Kona, Island of Hawaii
    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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    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Washer
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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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter through soaring ceilings, towering columns and an exotic water feature, step on to marble and stone flooring. This sprawling floor plan defines Hawaiian open air lifestyle featuring numerous multi-slide pocket doors and expansive lanai spaces. A Chef's dream kitchen designed to handle...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. 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...
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    96740, Kailua-Kona, Island of Hawaii
    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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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. 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...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
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    • Central Heating
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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    • Mountain Views
    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 5
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 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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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Hualalai Fairway Villa 104D - Festive Availability - Luxury Location!1 / 23
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Grill
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    Pet friendly
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    Reviewed 6 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    About this property
    Enjoy this serene surrounding with deep cultural history within close proximity to world class golf courses and fine dining. The place name 'Hainoa' references the mountain peak of Hualalai Volcano. Like its place name, the Hainoa Villa community sits at the peak of Hualalai Resort, overlooking...
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    96740, Kailua-Kona, Island of Hawaii
    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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    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Hualalai Ke Alaula 210A ~ Festive Availability ~ Panoramic Ocean 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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Mountain Views
    • Hot Tub
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    SKY VILLA1 / 12
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    This home is spectacular. It's on 5 acres of sheer beauty. It is clean, the linens are top notch and the kitchen has everything you need. It has a great grill for BBQ, a...
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    About this property
    Peace and tranquility is found on the Big Island of Hawaii! When you navigate the final stretch of the long circular drive of this magnificent villa, curve between deep green lawns and perfumed tropical Ginger. An immediate feeling envelopes you and says, 'I have arrived in paradise.'� You...
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    Location Information
    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • DVD Player
    • Internet Access
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 10-12 Beds: 3 kings - 2 queens - 3 singles This is 'IT'! The Flagship, plantation villa 'MALEKA'. Drive up to the resort size Porte cochere and you know you have ARRIVED IN PARADISE! Perched high up for the ultimate panorama ocean view, this villa sprawls over 2 acres of lush...
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    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    96740, Kailua-Kona, Island of Hawaii
    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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    • Air Conditioning
    • Terrace
    • Internet Access
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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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    96740, Kailua-Kona, Island of Hawaii
    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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    Location Information
    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hualalai Fairway Villa 116D ~Festive Available~ Beautiful Ocean & Golf Views1 / 25
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Internet Access
    • Washer
    • 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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    Location Information
    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • 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 condo 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...
    View all property information
    Location Information
    96740, Kailua-Kona, Island of Hawaii
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
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