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Vacation Rentals near Pillbox Hike

382 Kaelepulu Dr, Kailua, Oahu, Hawaii 96734-3312
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    Travelers to Kailua are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 264 Rentals in Kailua
    0.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    0.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Nancy's Kailua Cottage Makai1 / 32
    (8)Excellent
    0.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Nancy's Kailua Cottage Mauka1 / 15
    (9)Excellent
    0.8 miles from Pillbox Hike
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed June 4, 2021
    This was a good find! Clean as a whistle with nice amenities and very comfortable furniture indoors and out. Short walk to a nice stretch of beach with lots of trees, Kailua...
    Reviewed February 28, 2019
    This was the ideal spot for us, a pair of retired Canadians escaping a cold winter. Imagine walking just a few blocks to a gorgeous mile-long sandy beach, and just a few more...
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    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. Tourist License / Licencia de turismo N °: TATAXID#W40799764-01
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    Kailua, Oahu
    Rental Home - 1 Bathroom, Sleeps 4
    0.7 miles from Pillbox Hike
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
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    Smoking allowed
    About this property
    With 3 separate living spaces, this remodeled 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 lounging,...
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    Kailua, Oahu
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    0.4 miles from Pillbox Hike
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    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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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability1 / 13
    (76)Excellent
    0.3 miles from Pillbox Hike
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Kailua Beachfront - Licensed Rental #90/TVU-02481 / 29
    (161)Excellent
    2.4 miles from Pillbox Hike
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    Kailua, Oahu
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    2.6 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Kailua Beach "The Pink House"  100 Yards from Ocean1 / 18
    (25)Excellent
    0.7 miles from Pillbox Hike
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Very Close To Kailua Town And Beach! Last minute discounted rates!1 / 24
    (67)Very good
    1.9 miles from Pillbox Hike
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Kailua, Oahu
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    0.6 miles from Pillbox Hike
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    1.7 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Kailua Beach Vacation Cottage1 / 20
    (76)Excellent
    0.6 miles from Pillbox Hike
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Private Single-Family Home on large tropical landscaped lot1 / 30
    (56)Excellent
    1.7 miles from Pillbox Hike
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Kailua, Oahu
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Perfect Oasis, Steps To The Beach! 100% Solar!1 / 15
    (84)Excellent
    2.2 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    0.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Housekeeping Included
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Tropical Paradise In Lanikai1 / 27
    (27)Very good
    0.8 miles from Pillbox Hike
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Kailua, Oahu
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Kailua Oceanfront House1 / 30
    (94)Excellent
    2.8 miles from Pillbox Hike
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Large, beautiful, updated home w/pool, AC, mins from beach in Kailua!1 / 29
    (6)Excellent
    1.6 miles from Pillbox Hike
    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Kailua, Oahu
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    Kailua, Entire Home, yard, carport, BBQ, 7 min drive to bch1 / 30
    (14)Excellent
    1.3 miles from Pillbox Hike
    3 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 3
    0.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night1 / 37
    (122)Very good
    2.7 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beautiful Kailua Home, looking for a family to share it's Aloha1 / 29
    (28)Excellent
    1.0 miles from Pillbox Hike
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Perfect Family Home with private walk way to beach. 90 day rental1 / 29
    (3)Very good
    1.5 miles from Pillbox Hike
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    2.2 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.9 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    New Split AC in every room with awesome location!!!1 / 17
    (15)Excellent
    1.1 miles from Pillbox Hike
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.2 miles from Pillbox Hike
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!1 / 18
    (76)Excellent
    2.2 miles from Pillbox Hike
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    0.4 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Quiet, Private,  Beachy 2-bedroom,  Walk to Kailua Beach1 / 24
    (19)Excellent
    0.8 miles from Pillbox Hike
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Kailua, Oahu
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    0.3 miles from Pillbox Hike
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Kailua, Oahu
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.4 miles from Pillbox Hike
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach - Lanikai Cottage1 / 26
    (16)Excellent
    0.6 miles from Pillbox Hike
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Kailua, Huge Duplex, Home Office , yard, carport, BBQ, 15 min walk to beach1 / 26
    (20)Excellent
    1.8 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    1.2 miles from Pillbox Hike
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 3
    2.4 miles from Pillbox Hike
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Makana's Place1 / 21
    (41)Very good
    2.2 miles from Pillbox Hike
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Kailua, Oahu
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Absolutely Oceanfront - 60' Waterfall Lap Pool1 / 30
    (162)Very good
    2.6 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.5 miles from Pillbox Hike
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Kailua, Oahu
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    2.5 miles from Pillbox Hike
    9 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Kailua, Oahu
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 14
    Private  Studio with amazing view and private swimming pool!1 / 17
    (28)Excellent
    1.2 miles from Pillbox Hike
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Oahu
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Hale Maluhia Lanikai - Special On Beautiful Lanikai Home!1 / 19
    (14)Excellent
    0.1 miles from Pillbox Hike
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Kailua, Oahu
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Kailua Beachfront~private~newly renovated home w/stunning views1 / 29
    (6)Excellent
    1.8 miles from Pillbox Hike
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Kailua, Oahu
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.6 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Martins Hale - Private 1 Bedroom Studio1 / 12
    (38)Excellent
    2.1 miles from Pillbox Hike
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Kailua, Oahu
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Quaint Lanikai Cottage!  Such a gem!1 / 16
    (46)Excellent
    0.7 miles from Pillbox Hike
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
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    Suitability
    Pet friendly
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    Kailua, Oahu
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10)1 / 23
    (157)Excellent
    0.7 miles from Pillbox Hike
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    If you have 4 or 5 families and need a place to stay. This is for you. Great for big families. Half a block from beautiful Kailua Beach. You rent 5,000 square feet of this house...
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    Location Information
    Kailua, Oahu
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Wonderful, bright, breezy and recently upgraded house, 2 blocks from the ocean!1 / 21
    (2)Excellent
    0.7 miles from Pillbox Hike
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    Location Information
    Kailua, Oahu
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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