We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Woollahra Holiday Vacation with Pools

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$1,334 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Woollahra are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    20 Matching Rentals in WoollahraView all 91 rentals
    Sort by:
    Default
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern two bedroom apartment in a complex with gym. High ceilings, fully equipped stainless steel kitchen, reverse cycle A/C, security parking, stylish furnishings and generous balcony with city views make this Surry Hills apartment a fantastic place to stay whether you're in Sydney for a few...
    View all property information
    Location Information
    Woollahra, Sydney 2010
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Parking
    Suitability
    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...
    View all property information
    Location Information
    Edgecliff, Woollahra 2025
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and comfy, spacious 2 bedroom and 2 bathroom apartment with its own carspace for 1 vehicle, has a balcony, plus shared access to a lovely rooftop Pool and Spa :) The Space: - Master bedroom with King size bed - 2nd bedroom has 2 king singles - Fold down sofabed in the lounge room good...
    View all property information
    Location Information
    Edgecliff, Woollahra 2010
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    Suitability
    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...
    View all property information
    Location Information
    Vaucluse, Woollahra 2030
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • 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...
    View all property information
    Location Information
    Woollahra, Sydney 2027
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    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...
    View all property information
    Location Information
    Edgecliff, Woollahra 2027
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Balcony
    • Terrace
    • Washer
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious family townhouse is located in idyllic Diamond Bay, Vaucluse . Close to shops, cafes and transport as well as some of Sydney’s most scenic and breathtaking parks and harbour beaches. Featuring 3 bedrooms, 2.5 bathrooms and 2 outdoor entertaining terraces, it is ideal for a small...
    View all property information
    Location Information
    Vaucluse, Woollahra 2030
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Save time - get the best Woollahra rentals sent straight to your email!
    Get the List
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Grill
    Suitability
    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....
    View all property information
    Location Information
    Vaucluse, Woollahra 2030
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Parking
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    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)....
    View all property information
    Location Information
    Woollahra, Sydney 2021
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • 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...
    View all property information
    Location Information
    Woollahra, Sydney 2023
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sydney CBD York Street Newly renovated swimming pool Fabulous centrally located apartment, with parking, in the heart of Sydney's CBD. Minutes to Barangaroo, Harbour Bridge, and Circular Quay. Walking distance to Wynard station (100 meters, easy access to sydney airport), a host of local cafes...
    View all property information
    Location Information
    Woollahra, Sydney 2000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    Suitability
    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...
    View all property information
    Location Information
    Edgecliff, Woollahra 2027
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Darling Point is the gateway to Sydney and located just off exclusive Yarranabee Road with views across Rushcutters Bay Park to the bay of Darling Point is this stunning longer stay apartment named after its fabulous view. Luxury abounds for up to 4 x guests with 2 queen bedrooms, both with...
    View all property information
    Location Information
    Edgecliff, Woollahra 2027
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is in a lovely leafy green street, close to all public transport and positioned perfectly between Bondi Beach and The Sydney City. It is only 10-15 minutes by Train into the Sydney CBD, where you can see the Sydney Eye Tower views or to Circular Quay where you can see the Opera House...
    View all property information
    Location Information
    Woollahra, Sydney 2025
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Woollahra, Sydney 2027
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    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...
    View all property information
    Location Information
    Vaucluse, Woollahra 2030
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Edgecliff, Woollahra 2025
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    List your property
    Owner log in