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Holiday Rentals with Pools in Kailua

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    S$1,605 Average
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    Travellers to Kailua are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    17 Matching Rentals in KailuaView all 74 rentals
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    Plantation Charm in Kailua1 / 30
    (5)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $1991 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TAT-*******-7072-01 This property is a legally established dwelling that is rented for period of 30 consecutive days or more at any one time regardless of actual occupancy. Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New, light and airy one room cottage with queen sized bed, bath, kitchenette, out door sitting area by the pool. The sun provides for 70 % electricity used in this eco friendly Cottage. The lanai overlooks the tropical garden and the salt water swimming pool. Quiet and peaceful. The unit has...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This air-conditioned Studio is a private retreat away from home. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toaster, vegetable steamer, electric frying pan, mixer. Custom...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Washer
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and cheerful Tropical Garden Studio closer to award winning Kailua Beach and Lanikai. The sun provides for 70 % electricity used in this eco friendly Studio It is close to public transport, the city center, Kailua Beach, art and culture. You’ll love my place because of the location...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2020
    This vacation rental is nicely located on a beachfront piece of property. I stayed in the studio that has a view of the mountain and overlooks the pool. While the description of...
    Reviewed 6 July 2019
    This place was wonderful. Quiet and lovely beachfront home. We stayed in the Mountain Suite and took advantage of the saltwater pool with the waterfalls. The only issue was the...
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    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period. It will be available when you arrive. And they are legal - City is closing down illegal vacation rentals. Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lush landscape awaits you as you enter this gated tropical paradise tucked away beachside on a private lane, off Kailua Beach. Surround yourself with Hawaiian ambiance and the feeling of an amazing mini resort all to your own. Enter to this impressive 6-bedroom estate home surrounded by exotic...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful, covered lanai for...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and tropical flowers. The spacious yard is perfect for sun bathing, barbecuing or enjoying your favorite...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the largest, most private and secluded Estates on the island of Oahu. A spectacular beachfront location-at Kailua Shores Estate with the comfort of a resort, consisting of separate houses, newly remodeled, set on extensive grounds featuring a pool, hot tub, tennis court, barbeque, plenty of...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with a private pool. With 100 feet of...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
    Kailua, Oahu 96743
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Place in Paradise~Kailua Beach~ 5 bed~ Licensed Vacation Rental #90/TVU-02481 / 29
    (12)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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