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Greater Sydney Luxury Holiday Homes

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    Travellers to Greater Sydney are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    157 Matching Rentals in Greater SydneyView all 1,053 rentals
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    About this property
    Here for an extended beach retreat over the summer - Tamarama is in a prime position only a stones throw from Tamarama Beach, with all the facilities needed for a relaxing Sydney summer holiday.   What we love With a sleek and modern facade that demands attention this modern beachfront home...
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    Bondi, Greater Sydney 2026
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    The Edge is a property that’s going to make sure your luxury holidays in Sydney are the stuff of dreams. A holiday rental that was designed by renowned architect Renato D’Ettorre, just approaching this incredible home will take your breath away. You’ll enter into the open plan second floor and...
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    Coogee, Randwick 2034
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    About this property
    This property boasts 270 degree uninterrupted views extending from the city and Harbour Bridge through to and beyond North Head. The Gap is a perfect place to view the New Years Eve fireworks and the spectacular start to the Sydney to Hobart yacht race. Comprising interconnected kitchen, living,...
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    Vaucluse, Waverley 2030
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    7 Bedrooms, 9 Bathrooms, Sleeps 13 Quick View
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    About this property
    Look no further, The Ultimate Beach House is now available for family holiday rentals inWhale Beach. Situated on The Strand with direct beach access and also access via Whale Beach Rd, The Ultimate Beach House has everything that you could possibly want in a luxury holiday destination. Set out over...
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    Whale Beach, Pittwater 2107
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 13
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    7 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    About this property
    Oriented to the north and offering direct beach access from its world-class setting and dominated by ocean and headland views, this extraordinary residence is a breathtaking statement in design, dimension and quality. All floors are connected by an internal lift and the residence enjoys a...
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    Whale Beach, Pittwater 2107
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    One of the most amazing houses in Palm Beach is available for holiday rentals!!! Dune House has to be the ultimate holiday destination on the Northern Beaches and has absolutely everything that you could want in a luxury retreat. An absolute beachfront house on Sandy Beach in Palm Beach, Dune House...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    8 Bedrooms, 5 Bathrooms, Sleeps 22 Quick View
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    About this property
    It does not get much better than this!!! The perfect family property on one of the best beaches and in one of the best locations anywhere in the world. Absolute is the ideal family holiday house for those who need something on the grander scale. It is an amazing 8 bedroom house with all the...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 22
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    5 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    About this property
    Exquisitely designed by Melissa Collison and furnished, this elegant home is in one of Sydney's premier locations and will have you feeling like you never want to leave. Upon entering the property and heading up beautifully sculpted dark-wood stairs, the foyer, with rounded windows peeking into...
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    Vaucluse, Waverley 2030
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    This home offers the best of locations for a fantastic beach holiday stay right in the heart of Sydney! What we love We love that this home is so accessible to Tamarama Beach and its beautiful surrounds. Walking left to Bondi, or right to Bronte and Clovelly, you can explore to your hearts...
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    Bondi, Greater Sydney 2026
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Manly Seaside is a traditional style yet stylishly modern and luxuriously appointed double level, 4 bedroom, 2 bathroom, classic beach house that is within walking distance to Manly and the many attractions it has to offer including Manly and Shelly beaches. Once you park in the double garage to...
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    Manly, Greater Sydney 2095
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    One of the most amazing houses on the Northern Beaches is now available for holiday rentals over the summer months. The Amazing Bungan Estate is set on one of the largest flat level parcels of land on the Northern Beaches and is the most amazing location for holiday guests looking for the perfect...
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    Newport, Pittwater 2106
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    A rarity amongst holiday rentals, Bungan Beach Villa is an enthralling holiday home awaiting you in Palm Beach. The Northern Beaches best kept secret and home to a truly impressive beach-front property, this is an oasis sure to leave you stunned. Its exclusivity, beauty and surf makes this...
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    Newport, Pittwater 2106
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Central Heating
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    About this property
    Cocooned in eye-catching timber cladding, Sea Wood is a stand-out home both inside and out. With its highly sought North Bondi location, the very best of Sydney’s eastern beaches are at your fingertips. Sea Wood brings you the very best of contemporary coastal holiday living where breezy days and...
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    Dover Heights, Waverley 2026
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    The Queens Park Oasis is an exceptional Sydney retreat in the cities east, located in the peaceful neighbourhood of Queens Park this private oasis is within easy drive to the Sydney CBD and the eastern beaches of Bondi, Bronte, Tamarama Clovelly and Coogee. with an unasumming facade of a...
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    Waverley, Greater Sydney 2022
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    This resort style home right in the middle of Rose Bay really offers a fantastic holiday lifestyle. Designed by architects Smyth and Smyth, with interiors by Romy Alwill, the family home has been designed to make for easy entertaining, whilst also offering the very best of locations. What we love...
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    Rose Bay, Waverley 2029
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located opposite Nielson Park this is one of Sydneys most popular recreation areas offering both a glistening beach, national parklands and beautiful birdlife, all while perfectly positioned with Sydney Harbour views, only a fifteen minute drive to Sydneys CBD. Take a morning dip, a bush walk, a...
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    Vaucluse, Waverley 2030
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    A hidden gem in the heart of the iconic Australian beachside suburb of Manly, this unique property offers 3 bedrooms, all with ensuite bathrooms, across 3 architecturally designed levels. The ground level is complete with study/lounge and library that can double as a formal dining area, with an...
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    Manly, Greater Sydney 2095
    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
    TO INSTANTLY BOOK THIS PROPERTY YOU MUST BE OVER 23 YEARS OF AGE (CHILDREN TRAVELING WITH ADULTS ARE  WELCOME)  Picture a stunning secluded beach offering amazing views across a seemingly endless azure ocean. Imagine gazing out over the beautiful golden sands and watching the beautiful sun rise in...
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    Newport, Pittwater 2000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Overlooking one of the most beautiful waterways on the Northern Beaches and the famous Barrenjoye Light House, Sereia is an amazing holiday house that is perfect for the luxury family getaway. There are not many places where you can feel so relaxed and be in such a private location, yet you are...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Eclipse is a spectacular luxury holiday rental home celebrated for its incredible oceanfront position in Palm Beach that will leave you feeling as though you are riding the Pacific waves. With stylish and chic interiors, Surfside offers luxury, decadence, and effortless style in a private paradise...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Balcony
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    About this property
    If you’re looking for a home that’s extra special, this luxury holiday home is the perfect choice! As soon as you arrive you’ll be astounded, and turn right as you enter to reach the glorious living and dining area where a table for ten sits beside a huge picture window – perfect for fun family...
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    Clontarf, Manly 2093
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    As you set foot on to Pacific Place you’ll feel as if you’re arrived at your own luxurious coastal resort. And nothing says resort living like the lush gardens and the unforgettable huge wooden entry doors that greet you at Pacific Place. When you open those doors there’s no doubt as to why this...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This prestigious waterfront apartment features the most spectacular views of Sydney Harbour and epitomises Sydney city living at its absolute best. La Corniche was designed to frame the almost-touchable panoramic view of Sydney Harbour, the iconic Opera House, Bridge, Luna Park and CBD skyline....
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    McMahons Point, North Sydney 2060
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    About this property
    A refreshing escape that combines amazing water views, a premium Sydney harbourside location and a luxurious three-level family home, Mosman Retreat is your ultimate destination. The outdoor swimming pool, rumpus room with garden access and large terrace with harbour views is sure to leave a...
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    Mosman, Greater Sydney 2088
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    MANLY HARBOUR VILLA1 / 24
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Manly Harbour Villa is a stunning waterfront home. Positioned in one of Sydney's most iconic and popular suburbs this stunning Spanish inspired Villa offers spectacular views and facilities. Boasting 5 beautifully appointed bedrooms, tranquil outdoor entertaining areas, a fantastic waterfront pool...
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    Manly, Greater Sydney 2095
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
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    About this property
    Chill and relax in paradise in this ultimate Bali Resort home at Avalon on Sydney’s northern beaches. This stunning resort style property set on one acre, with five massive villa bedrooms and stunning entertaining spaces, just one kilometre from Avalon Beach and Pittwater, is the perfect Aussie...
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    Avalon Beach, Pittwater 2107
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    One of Palm Beach's finest homes located at the prime north end of Iluka Road, Palm Beach. - Magnificent Pittwater views to Lion Island and beyond - Easy-flowing three storey beach house in a gorgeous location - Sunny and protected north-west aspect - Large decking area and level lawns go directly...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    Absolute direct Pittwater beachfront, Beach Haven is located on one of Sydney's most sought after beach locations. This fabulous six bedroom house is in the ideal position for a family holiday. With accommodation to sleep an extended family,  air conditioning and access to Sandy Beach Beach Haven...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Fabulous, sheltered north aspect and views spanning the length of Palm Beach to Barrenjoey Head and the symbolic lighthouse Located on Florida Road, away from the crowds, but with direct access to Ocean Road and Kiddies Corner. Built across 3 levels - Each level enjoys the views and has its own...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This luxury home is a stunning Spanish mansion is cantilevered on the side of a cliff, so the water views are out of this world. For a fine stay in Sydney, you can’t go wrong with this home – in renovating, the owners have respected the past by keeping many of the period features, while pouring...
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    Vaucluse, Waverley 2030
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    Spend your days in the ultimate luxury pad, where nothing but a gate is in the way of you and the golden sands of Bronte beach. Architecturally-designed and in one of Sydney's most coveted addresses, this opulent elevated home boasts panoramic views of the ocean and the bustling beachside hub that...
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    Bronte, Waverley 2024
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This magnificent Bondi apartment has a 180-degree view of world famous Bondi Beach and the coastline. Situated in the infamous ‘Pacific Bondi’, this apartment couldn’t get you any closer to the action, or in more style. What we love We love the incredible location and views this apartment has to...
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    Bondi, Greater Sydney 2026
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Like with all lighthouses perched atop cliffs with a guiding light to keep ship travellers safe, the Avalon Lighthouse is perched atop Bangalley Head and as its name suggests, this abundantly light home makes you feel safe as you watch the waves crash against the renowned Avalon Headland profile...
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    Avalon Beach, Pittwater 2107
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to Ohana. This stunning beach side residence is strikingly beautiful, the views and interiors are both luxury and comfort combined. The beautiful Hawaiian name Ohana, meaning family, was gifted to this home as its owners injected love and care into the renovations ensuring the most stunning...
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    Bilgola, Pittwater 2107
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Perfect for your next photoshoot location The Haven overlooks sparkling Careel Bay and its flotilla of boats and ferries. This glorious, luxurious yet relaxed, North facing home is bathed in sunlight from dawn until dusk and boasts its own private jetty. The Haven is nestled at the bottom of a...
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    Whale Beach, Pittwater 2107
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Steeped in local history, is the completely private, awe inspiring and jaw droppingly beautiful Stonehouse. Restored to its original grandeur with the addition of every possible luxury you can think of, perched high on Bilgola Plateau with 180 degree views overlooking Bilgola Beach and beyond, The...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    A weekend of splendor awaits in this newly renovated 6 bedroom waterfront home, fabulous for a family weekend away. Upon arriving at this extremely private Code dzur inspired 4 level home, with lift and inclinator; you are welcomed by an easy access semicircular driveway that leads to the...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    About this property
    Located less than a stones throw from Lucinda Park and both Sandy and Snapperman Beaches on Iluka Rd in Palm Beach, Viburnum is an amazing house that offers everything that you could want for a weekend getaway or a summer holiday on the Northern Beaches. Viburnum is a fantastic 2 level house with...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    The scenic Coogee to Bondi walk at your doorstep. You will adore this architecturally designed coastal property. Gordon's Bay is a private suburb nestled in-between Coogee and Clovelly, often described as the Amalfi of Sydney's coastline. This beautiful home is walking distance to Coogee and...
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    Coogee, Randwick 2034
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Patio
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Nestled in Sydney’s eastern beachside suburb of Clovelly, Clovelly Pavilion, offers three substantial levels of pure holiday indulgence. This Victorian renovation has an impressive modern interior providing you loads of options for entertaining, such as the open plan living-dining, pool, and...
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    Clovelly, Randwick 2031
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    The Hamptons inspired Palm Beach Shores overlooks the golden sands of the Pacific Ocean and is situated right in the dress circle of Australia's iconic beach paradise, Palm Beach. The relaxed, informal atmosphere of this beautiful, generously proportioned beach home is filled with light and...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    About this property
    You'd be hard pressed to find a similar home in Manly that is so spacious (900 sqm to enjoy), beautifully styled and appointed, stunning harbour views, multiple living areas to enjoy, established gardens, your own gym and so well positioned to beaches and Manly's main village as well as the ferry...
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    Manly, Greater Sydney 2095
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A stunning 4 bedroom property located 2 minutes walk to the popular and iconic Whale Beach and just across the road from the fabulous Boathouse Group's Whale Beach Deli. This spectacular home offers incredible views, open plan living and dining - perfect to take in the views whilst cooking, eating...
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    Whale Beach, Pittwater 2107
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one of the largest properties in Palm Beach, the grandeur of Palm Beach estate is unmistakable and this holiday rental accommodation offers guests a truly majestic experience. Defined by its contemporary luxury, this spacious home is truly unique and one of a kind and distinguished by its vast...
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    Palm Beach, Pittwater 2108
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Sustainable living, contemporary design and natural materials can be experienced in this stunning Coogee house called Kenzai, whose meaning relates to a healthy living environment. This property offers luxury, privacy and contemporary design features whilst also being a comfortable home that...
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    Coogee, Randwick 2034
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Balcony
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    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With Ocean views and just a short 200m walk from stunning Shelly Beach, this recently completed luxury home is the perfect place for a relaxing beach holiday. The main living floor comprises a spacious lounge room, sunny internal courtyard and a stunning modern kitchen-dining area opening onto a...
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    Location Information
    Manly, Greater Sydney 2095
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Balcony
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you looking for the perfect family beach holiday house? Beachfront on Bungan is the house that has everything that you want for the ideal family holiday….and then more to make it even better! The house is privately located down a restricted driveway with direct access to Bungan Beach. The first...
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    Location Information
    Newport, Pittwater 2106
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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