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Woollahra House Rentals

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    Travellers to Woollahra are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    40 Matching Rentals in WoollahraView all 92 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chic Terrace House Paddington near Darlinghurst & Rushcutters Bay incl Breakfast1 / 26
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Indoor Pool
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    About this property
    Luxury Home with Pool in Bellevue Hill WHAT WE LOVE In Sydney’s exclusive Bellevue Hill, this luxury home comes with all the trimmings. Combining vast living spaces and quiet reading nooks, there’s the perfect spot to sit and contemplate. Cook a meal for the family in the sumptuous kitchen and...
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    Woollahra, Sydney 2023
    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
    Paddington, or 'Paddo,' is one of Sydney's coolest suburbs but its famed Victorian terraces are not known for being large and well lit. That's what makes our place so special. It's twice the size of most other homes in the area, with a stunning mix of contemporary luxury and period features. It's...
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    Edgecliff, Woollahra 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pearce St is the distinctive design you’d expect from the award-winning Tribe Studio practice. And you get a sense of that outstanding quality upon arrival at this peaceful bayside home. After parking in the garage, or in the driveway, you’ll find the entry via a private side path. Waiting inside...
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    Woollahra, Sydney 2028
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    WATSON'S BAY COTTAGE - The Scout Group1 / 35
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
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    Reviewed July 26, 2017
    Watson's Bay Cottage is a lovely place to stay while visiting Sydney. Absolute waterfront on Watson's Bay with easy access to the ferry services. The standard of the house was...
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    About this property
    The Space Retreat to this exclusive location and enjoy this 1920’s Historic Beach Bungalow, only a 25 minute drive from the inner city and with transport links close by for you to jump on for a Sydney adventure or corporate visit. With waterfront location & spectacular harbour views, this luxury...
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    Watsons Bay, Woollahra 2030
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Central Heating
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    Pet friendly
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    About this property
    Cozy terrace in the heart of the hustle and bustle of trendy inner-city Darlinghurst. Only a short stroll to the hippest cafes, Hyde Park, boutique shops and transport to anywhere in the city. Our whole house has recently been renovated and styled with vibrant colours and eclectic decor befitting...
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    Woollahra, Sydney 2010
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    About this property
    Our exposed brick walls, sunny courtyard and period touches will immediately make you feel at home in Sydney's most chic neighbourhood. Located on a quiet, tree-lined street only a block away from the restaurants, bars, cafes and designer shops of Oxford St, our Paddington terrace practically oozes...
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    Edgecliff, Woollahra 2021
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soothing and serene, Woollahra Haven is the inner Sydney escape with idyllic outdoor living and delightful city views. Offering contemporary luxury living with multiple living areas, five bedrooms, swimming pool and master suite with balcony, you’re sure to discover your own private nook to hide...
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    Edgecliff, Woollahra 2025
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Eastern Suburbs Luxury & Sophistication1 / 22
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2017
    AMAZING location, AMAZING house that suited all of our needs, Wooi is an amazing host! Will be back.
    Reviewed July 26, 2017
    It's our home away from home...the place is so cozy it made our stay so much fun and memorable! exactly how it was described, easy accessible to public transportation and near...
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    About this property
    Ideal for couples, business travelers, families (with kids & extended family) & within 10 mins walk to Bondi Junction Westfield Mall, Bondi Junction Station, Double Bay, Cooper Park Tennis. 10 mins drive to Bondi Beach, Watson's Bay, Paddington, Sydney CBD, Sydney Opera House, The Rocks, Darling...
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    Woollahra, Sydney 2025
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
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    • Waterfront
    • Terrace
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    • Ocean Views
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wind down in style at this exclusive Art Deco Sydney harbour side idyll set within leafy surrounds, and just a casual stroll across to the picturesque Camp Cove Beach. Camp Cove Beach Haven is a private, secluded escape for families, situated in historic Watsons Bay at the South Head entrance to...
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    Watsons Bay, Woollahra 2030
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    HOLIDAY PROPERTY: Celebrate in this property over the Christmas Holidays Immerse yourself in the Sydney Summer from this stunning four bedroom family home in exclusive Vaucluse, be greeted by a cool and calming ambiance which is created by the rich holiday feel and clear colour palette of the...
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    Watsons Bay, Woollahra 2030
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    A Top-Shelf Retreat in Paddington1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed March 25, 2018
    The place was great- very comfortable. More important, the instructions were easy to follow, and communication with the property manager was seamless. I walked to the market...
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    About this property
    Marvel at your elegant surroundings in this stylish yet sophisticated three bedroom cottage, located on one of Paddington's most quaint and wondrous streets. As you pull up to the charming red door and vine-swathed facade of this double fronted home, you will instantly feel indulged in style and...
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    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brimming with easy-going elegance, Hamptons at Nielsen Park is a harbourside family sanctuary that enjoys a quiet, idyllic Vaucluse location, intimate Sydney harbour views and is footsteps to the beach and parks. Feel at ease in the Hamptons-style interior where you have space to share in the...
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    Vaucluse, Woollahra 2030
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    The Woollahra Maison is a stunning Family home in the heart of the Woollahra Village in Sydney's Eastern Suburbs. This sophisticated retreat features three bedrooms in the Main house and a fourth bedroom with ensuite on the other side of the lawn courtyard - perfectly suited for teenagers or...
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    Woollahra, Sydney 2025
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Air of Elegance in Paddington1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed June 8, 2017
    We stayed for 5 nights at Napier Street, it is honestly even more gorgeous than the photos! Home Away From Home were amazing to deal with, key collection was simple and the...
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    About this property
    Experience the absolute best of our amazing city from this exquisite three bedroom, two bathroom terrace, situated in the fashionable hub of Paddington. This immaculately styled home is striking with elegant accents of grey and white and a hint of gold for good measure; the furnishings throughout...
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    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A magnificent view should be enjoyed from a comfortable chair in a beautiful room of a superb home and that is exactly how you will enjoy The Harbour View when staying in this opulent Point Piper home. Built circa 1920 with the curves, parquetry floors and high ceilings typical of grand buildings...
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    Woollahra, Sydney 2027
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Harbour views, stylish interiors and perfect positioning to explore the rest of Sydney - this exquisite Vaucluse home has it all. Located near the foreshores of Sydney Harbour, the home is sunlit, spacious and perfect for a family stay, decorated in eclectic pastels and hardwood finishes. On the...
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    Vaucluse, Woollahra 2030
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Feel right at home in this fully furnished, architecturally designed three bedroom, two bathroom terrace that spans over three levels providing a vast space that is flooded with light from the many windows. The countless outdoor entertaining areas are a true feature of this gorgeous space which...
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    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Mona Vista, Darling Point. This stunning luxury home in Sydney premier location is truly an oasis in the city. Guests will enjoy a unique lifestyle experience that includes spectacular views which pans across Rushcutters Bay, to Sydney Harbour, to the city skyline and beyond. This...
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    Edgecliff, Woollahra 2027
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in the privacy of a large stylish 3 bedroom house with a big pool/BBQ/entertainment area, close to close to Watson’s Bay, Bondi Beach and Vaucluse. The property features a large open plan living and dining area that leads effortlessly to the private outdoor entertaining area and pool access....
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    Vaucluse, Woollahra 2030
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Patio
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    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re looking for Sydney CBD accommodation that gives you peace and privacy, this incredible apartment for rent by owner is your dream holiday home. An Art Deco warehouse conversion that’s set in the treetops, the building is steeped in history (it was originally McGraphs motors in the 1940s)....
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    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful 3-bedroom multi-level apartment in leafy Bellevue Hill with harbour views and sheltered garden. Very well located, just a short bus ride or walk to Bondi Junction and walkable to Bondi beach or Rose Bay, giving easy access to the city. Ideal for families or 2 couples, with two separate...
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    Woollahra, Sydney 2023
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    As seen in Belle Magazine Autumn 2018 Built circa.1904 this handsome Edwardian terrace has been lovingly restored and features many period furnishings synonymous with the era making this the perfect base for you to explore our amazing City. Situated in a prime location this three-bedroom two...
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    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Located in one of Sydney's most coveted residential areas in a very quiet street, this contemporary terrace combines the best of industrial and traditional design to create a homey but stylish sanctuary for your stay. The open plan living, dining and kitchen space boasts a sleek polished...
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    Woollahra, Sydney 2022
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a quiet and historic East Sydney laneway, this ultra-modern house is around the corner from iconic Bill & Tony’s café and City Gym and a short walk to Cook & Philip Park pool, Hyde Park and the centre of the CBD. Surrounded by historic 1850s terraces, the house is built over two levels...
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    Woollahra, Sydney 2010
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Washer
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxury holiday home sits in a position of perfect elevation, making the most of the view to Sydney harbour. A tastefully furnished rental home in one of the most prestigious neighbourhoods in Sydney, accommodation doesn’t get much more luxurious than this! On arriving through the grand...
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    Woollahra, Sydney 2023
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Super Cute City Cottage1 / 19
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed May 17, 2017
    It was a real pleasure to stay in this delightful period cottage in the heart of Paddington. Everything was immaculate and it was very well equipped. The excellent location...
    Reviewed April 28, 2017
    Great location, sweet house and excellent support by the company that rents this place out. “The communication and information provided by this company was complete and clear...
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    About this property
    This charming classic cottage built in 1841 offers a truly unique city experience in the heart of Paddington. It's only 50 metres from the famous Oxford Street so it's in the heart of the action and the perfect place for those looking to have some fun and explore this famous City. It also has the...
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    Woollahra, Sydney 2021
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Unusually wide cottage 50 metres from Queen Street. Featuring an unusually wide 6.85 metre frontage, this classic turn of the century cottage has been completely transformed by a stunning renovation, creating a wonderfully spacious, tasteful two-storey home. Set in a quiet enclave opposite...
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    Woollahra, Sydney 2025
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set amongst established grounds this recently renovated grand Edgecliff home really is a true Sydney beauty. What we love We love the grand beauty of this magnificent period home, the superb renovation and the space and elegance it offers to guests. What the client loves The client loves the...
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    Edgecliff, Woollahra 2027
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This immaculate house is the perfect place for those looking to have a stay in Sydney. Located in the heart of Paddington just a few steps to Oxford Street and a short stroll to Centennial Park, Woollahra, Paddington Five Ways, Fox Studios and walking distance of Surry Hills, Darlinghurst and the...
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    Woollahra, Sydney 2021
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Spacious and classic in Woollahra1 / 19
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Reviewed 3 weeks ago
    The house in Woollahra was spectacular - plenty of space for all our family, great living space with kitchen and dining opening out to the garden. Lovely bedrooms (particularly...
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    About this property
    Urban living at its best, this spacious four-bedroom home designed by architect Alexander Tzannes, is only a short walk from Woollahra's Queen Street shopping village. This classic-contemporary house has a northerly aspect and parklands at the front and rear and boasts large rooms with high...
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    Woollahra, Sydney 2025
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This grand Victorian home is located in the heart of Woollahra. It offers both contemporary and period features, a beautiful landscaped garden with leafy surrounds, as well as a heated outdoor pool. What We Love We love the charm and character this elegant Victorian home offers, as well as the...
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    Edgecliff, Woollahra 2025
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to prestigious suburb of Vaucluse and discover the Bohemia way of life. Be greeted by our jaw dropping-ly impressive family home with arguably the best views over Watsons Bay. Bohemia also has direct harbour access through a shared pathway that meanders down to Gibsons Beach perfect for...
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    Vaucluse, Woollahra 2030
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This truly is one magnificent Point Piper home! Set on a level site, with a large wrap around balcony and accompanying pool, overlooking Rose Bay Marina, famous Catalinas Restaurant and the sea planes landing and taking off, theres not a lot left off the list here. What we love We love the...
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    Woollahra, Sydney 2027
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A grand four-storey home with direct private access to one of Sydneys best kept secret beaches. Nestled in the foreshore of Vaucluse, a mainstay in the top ten postcodes in the country, it combines luxury and natural beauty in equal measures. Enter the house on the living floor, where the kids can...
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    Location Information
    Vaucluse, Woollahra 2030
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in Woollahra's premier tree lined street is the Woollahra Villa, a perfectly peaceful enclave awaiting you. This spacious, luxurious three-level home with expansive gardens and views offers the best of the best when it comes to vacation or did someone say stay-cation? The main level boasts...
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    Location Information
    Edgecliff, Woollahra 2025
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Freestanding and full of natural light, this beautifully designed property is within walking distance to great cafes, art galleries, restaurants and gourmet food shopping. Recently renovated to the highest standard with custom bespoke furniture from around the world, this luxury stay features a...
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    Location Information
    Woollahra, Sydney 2021
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set on a high hill overlooking Rushcutters Bay, Sydney Harbour, and beyond, the Darling Point Pad features extraordinary interiors and sensational viewing decks overlooking a large private garden. This two bedroom apartment has the ambiance and romance of a villa on the French and Italian...
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    Location Information
    Edgecliff, Woollahra 2027
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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