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Holiday Rentals with Pools in Kailua

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    RM 3,564 Average
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    Travellers to Kailua are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    10 Matching Rentals in KailuaView all 56 rentals
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    Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $2201 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Plantation Charm in Kailua1 / 30
    (5)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this Charming Cottage in beautiful Lanikai. Enjoy the convenience of relaxing on a beautiful Short walk to the beach nightly, and get lost in the comforts of a cozy home with an efficiency kitchen and your own washer and dryer in the home. There is One split AC unit. Property has a Large...
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    Location Information
    96734, Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The...
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    96734, Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement elegant indoor and lush outdoor spaces. Live each moment of your relaxing...
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    96734, Kailua, Oahu
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how...
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    Location Information
    96743, Kailua, Oahu
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can be divided into three...
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    Location Information
    96734, Kailua, Oahu
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note the homeowner lives on-site, in a completely separate unit with some shared amenities and may be present during your stay ** Experience an idyllic Hawaiian stay at this Kailua vacation rental home. Outfitted with a pool, patio and great location just 2 miles from Kailua Beach Park,...
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    Location Information
    96734, Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,...
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    Location Information
    96734, Kailua, Oahu
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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