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Waikoloa Luxury Holiday Homes

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    Travellers to Waikoloa are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    35 Matching Rentals in WaikoloaView all 238 rentals
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Welcome to Kolea Hale Moana, one of the many stunning luxury vacation rental from Time & Place. Main house and separate guest house can accommodate up to 10 guests Stunning outdoor living space with private pool, hot tub and spacious lanai Beautiful courtyard with stone tiles and water feature...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Mountain Views
    • Washer
    • DVD Player
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    • Waterfront
    • Ocean Views
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious 4 bedroom villa in the exclusive Kauna'oa subdivision of the Mauna Kea resort. This ocean view property features a private pool and spa, 2 golf carts on site. Each bedroom boasts a flat screen TV and wifi. Kitchen features Viking appliances including 6 burner range. Rental includes use of...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Mountain Views
    • Ocean Views
    • Cable/satellite TV
    • Children's Pool
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    Pet friendly
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    About this property
    Kolea Ocean Combo is composed of two elegant 3 bedroom units, unit 1E and 2D for a total of 6 bedrooms. They are located in neighboring buildings. These units are inside the beautiful 5 star resort Kolea at Waikoloa Beach Resort. Be in love and enjoy these tropical paradise getaway you can call...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 15
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    Hualalai Hillside Villa 4102 - Premier Location, upgraded with Stunning Views1 / 23
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground floor Hillside Villa. Receding glass pocket...
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    Waikoloa, Kohala Coast 96740
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    About this property
    The Mauna Lani Bay Hotel & Bungalows are closed for renovations until November 2019. Please contact a Villa Specialist for more details. A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. This luxury villa -...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Mountain Views
    • Waterfront
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aloha and welcome to Kolea Villa! Unit 6D was recently added to our premier group of designer properties. Located on the ocean-side of Kolea, redecoration in the Hawaiian-Pacific Rim Fusion style will bring you 5-star elegance and the soothing rest you long for. With its own distinctive character,...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mauna Lani Point Fairway and Ocean View1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    The Mauna Lani Bay Hotel & Bungalows are closed for renovations until November 2019. Please contact a Villa Specialist for more details. A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. This luxury villa -...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Mauna Lani Bay Hotel & Bungalows are closed for renovations until November 2019. Please contact a Villa Specialist for more details. A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. This luxury villa -...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
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    • Housekeeping Included
    • Sauna
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Mauna Lani Bay Hotel & Bungalows are closed for renovations until November 2019. Please contact a Villa Specialist for more details. A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. Welcome to Signature...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Mauna Lani Bay Hotel & Bungalows are closed for renovations until November 2019. Please contact a Villa Specialist for more details. A tax increase applies as of January 1st 2019. Please see House Rules section for more information, or consult with your Villa Specialist. This luxury villa -...
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    Waikoloa, Kohala Coast 96743
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome you to our worry-free 1,460 foot Premium Luxurious Ocean-View 2 bedroom corner, upper-floor villa. Enjoy the morning birds and sunset ocean views from the villa lanai, which backs on the Robert Trent Jones Jr.-designed Waikoloa Beach Golf Course set into a lava field. This corner unit...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    With a stunning Pacific backdrop, this 1,677-square-foot haven indulges with private lanai and separate living area. Enjoy conveniences like a laundry room with full washer/dryer, gourmet kitchen for cooking meals, high-speed Internet, flat screen TV and central air. Then relax with hotel quality...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The whitest sand beach, the bluest ocean, and the greenest gardens with the ever-present sweet fragrance of exotic flowers inspiring relaxation. Views of open lawn with tropical flowers and foliage, including coconut, palm, bread fruit (ulu), and banana and mango trees; waterfall and fountain...
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    Waikoloa, Kohala Coast 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Halii Kai 15F1 / 38
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting perched above the surf, Hali'i Kai 15F, provides one of those rare oceanfront views. This 3-bedroom 3-bathroom penthouse has an open floor plan on its first floor that allows you to entertain guests comfortably from the living room, dining room, kitchen or lanai. No matter which of these...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this fabulous newer home with an ocean view. Sitting in a unique West Hawaii neighborhood that offers its guests the convenience of nearby shopping, restaurants, stables, community pool, tennis courts, and golf course play at special rates. Yours to enjoy, some of the many features of this...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Exquisite Three Bedroom, Three Bath Ocean view Villa (AC & Resort Fees incl.)1 / 23
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other. It is at this point of convergence that we have chosen to situate our residential community Hali’i Kai at Waikoloa. Perched on a bed of lava overlooking the coast, our...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Views of the West Maui Mountains, and Mount Haleakala; private lanai; 1 queen bed, 2 twin beds  and 1 sofa bed; second bedroom in some units are lofts; each suite has been individually furnished and designed to create a unique setting. At Kamaole Sands, the three “Rs” are “relax,” “refresh,” and...
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    Waikoloa, Kohala Coast 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Majestic ocean views define this 1,403-square-foot air-conditioned “home away from home.” With full kitchen and laundry room, your villa also provides a private lanai, ceiling fans, large screen TV and high-speed Internet. Unplug and tuck into hotel quality linens for a good night’s rest on king,...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oceanview 2Br Halii Kai Condo12A- 50% OFF WINTER SPECIAL OCT 27-NOV 131 / 26
    (43)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2018
    Believe what you’re reading in all of the reviews... Peggy’s condo is truly a special place. Our family of 5 spent a wonderful Christmas at Halii Kai and look forward to being...
    Reviewed 2 May 2018
    We rented this condo for a week and absolutely loved it. The condo is decorated beautifully, the view is to die for and the location is perfect! Waikoloa has great shops and...
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    About this property
    My property may show available but please allow me to confirm these dates prior to a reservation request or organizing your flights since your desired dates may create gaps of less than a week on either side of your stay that are difficult to fill.. This is a magnificent property so I do not want...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Oceanfrt 2br Condo-Halii Kai 14C- 50% OFF WINTER SPECIAL OCT 27-NOV 91 / 23
    (55)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Internet Access
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2018
    We booked unit 14C for our family of 4 for 9 nights and really enjoyed our stay. The unit is exactly as advertised...well stocked with everything you need. Condo is...
    Reviewed 21 August 2018
    This condo was absolutely amazing. Not only was it located in a prime location with a magnificent view, but it had all the necessities you would need for a wonderful vacation...
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    About this property
    My property may show available but please allow me to confirm these dates prior to a reservation request or organizing your flights since your desired dates may create gaps of less than a week on either side of your stay that are difficult to fill.. This is a magnificent property so I do not want...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    BREATHTAKING TRUE OCEANFRONT LUXURY VILLA SPECIAL1 / 28
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    I cannot rate the villa I booked as there was a mix-up with the owner's calendar. The title review is an average rating so as not to affect John R's rentals since I don't know...
    Reviewed 5 June 2018
    My family spent a wonderful week at this beautiful oceanfront condo. The view is amazing. The villa is nicely decorated and has everything you need for a vacation stay. The...
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    About this property
    ***BRAND NEW FOLD-A-WAY DOORS INSTALLED JUNE, 2017, REPLACES TRADITIONAL SLIDING GLASS DOOR THAT ONLY OPENS HALF WAY. THERE ARE ONLY A COUPLE UNITS IN HALI'I KAI THAT HAVE THESE INCREDIBLE FOLD-A-WAY DOORS. WITH THESE DOORS OPENED, YOU HAVE A COMPLETE UNOBSTRUCTED VIEW OF THE OCEAN FROM YOUR...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Washer
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Paradise! From the moment you walk in you see amazing ocean, golf course and volcano views. This gorgeous 3 bedroom, air-conditioned, corner unit is situated in one of the best locations within the Hali'i Kai Resort. Beautifully decorated and well-appointed with elegant tropical style...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a ground floor 3 bedroom, 2 bathroom condo. The condo has been decorated in island style decor. The condo has beautiful views of the ocean from the living room, master bedroom, and kitchen. The community pool can be seen from the lanai and is a very short walk. There is a large Weber...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Halii Kai Resort - Premium Ocean View 16G - Prime Location1 / 24
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Terrace
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    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Condo, 3 Bedrooms, 3 Baths, (Sleeps 6) Premium Ocean View Residential interior by Fine Design Hawaii. Features: - Largest floor plan at Hali'i Kai - 1930 square feet including lanais - Sunset and Ocean views from both lanais - Directly across from the pool/Ocean Club - Weber Genesis Grill -...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,677-square-foot Waikoloa town home is so comfy you may never want to leave! Savor meals from the gourmet kitchen on your private lanai. You’ll love the full laundry room, living area with large screen cable TV, high-speed Internet, central air and ceiling fans. Then dream away amid king,...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,677-square-foot Waikoloa town home is so comfy you may never want to leave! Savor meals from the gourmet kitchen on your private lanai. You’ll love the full laundry room, living area with large screen cable TV, high-speed Internet, central air and ceiling fans. Then dream away amid king,...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Halii Kai at Waikoloa 1 Bedroom Garden View Villa1 / 22
    (1)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2016
    It seems that all of the units are similar in size, with three bedrooms, but some of the bedrooms are locked off for the one and two bedroom rentals. There are two basic...
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    About this property
    BIG ISLAND OF HAWAII 1-Bedroom / 2-Bath Garden View Villa Overlooks the fairways of the Waikoloa Beach Golf Course. The villa comes with a fully equipped gourmet kitchen, high-speed Internet, large screen cable TV, fully equipped laundry room with full-size washer and dryer, soap and laundry...
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    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Hali'i Kai - Spectacular Ocean View 2 Bed End Unit1 / 14
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
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    • Balcony
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    My Husband and I really enjoyed this 2 bedroom, 2 bath condo with ocean views!It is located in Waikoloa about 20 minutes north of the Kona airport. The gated community is very...
    Reviewed 8 July 2016
    we visited this place with my wife,daughter and my son in law, we feel this is the right place to relax we stayed in unit 6H,unit was having all the appliances which we expect...
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    About this property
    If you are looking for the best unit in the best resort, look no further. Hali'i Kai is a 30-acre gated oceanfront complex on the Big Island of Hawaii with unbeatable amenities. Our villa #11D has the best 2 bedroom ocean view location in the complex. Our spacious second story end unit overlooks...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Washer
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    • DVD Player
    • Children's Pool
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ALOHA! FOR CORRECT CANCELLATION POLICY PLEASE CONTACT US OR DOWNLOAD RENTAL AGREEMENT DURING BOOKING Welcome to your 'home away from home' in the paradise! You will find there everything you need for your dream vacation: from very comfy beds to fully equipped kitchen and full set of beach gear and...
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    Waikoloa, Kohala Coast 96738
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,082sf slice of paradise says “aloha” with incredible ocean and resort views! Touches include a gourmet kitchen, ceiling fans, central air, furnished lanai, high-speed Internet, cable TV, laundry room with washer/dryer and complimentary bathroom toiletries. Sleeps 4 in 1 King plus 1 Full or 2...
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    Location Information
    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kamaole Sands is one of the most popular condominium resorts on Maui. Accommodations are spacious and comfortable with fully-equipped kitchens and private lanais. Four complimentary tennis courts, large swimming pool, sun deck, two jet spas, and nine barbeque areas are on property. Overlooking...
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    Location Information
    Waikoloa, Kohala Coast 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    B4 Waikoloa Beach Villa with Hilton Waikoloa Pool Pass thru 2018 and 20191 / 35
    (16)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in the peaceful surroundings of Waikoloa Beach Villa B4 that features three bedrooms, three full bathrooms, and accommodates up to eight guests. Cool off in one of the two community swimming pools and in the evening, enjoy a soak under the stars in the outdoor hot tub. The villa includes the...
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    Location Information
    Waikoloa, Kohala Coast 96738
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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