Pet-friendly vacation rentals in Woolloomooloo

Self-Contained Cammeray Guesthouse near CBD and Beaches

Relax on the sun-drenched veranda of this charming federation guesthouse overlooking Green Park. Perfect for couples, business travellers, small families and dog owners, this fully self-contained retreat offers a private entrance, no shared living spaces, free all-day street parking and all the comforts of home. Enjoy direct access to parklands, playgrounds and walking paths, while Cammeray's cafés, restaurants and public transport are just moments away. North Sydney and Sydney CBD are close by.

Deluxe Harbour Bridge View+ Free Parking Sleeps 5

Enjoy a stylish experience at this centrally located apartment. 2-bedroom 1 bathroom apartment, free parking 2 queen size beds, 1 rollaway bed to set up Stunning views overlooking Sydney Harbour. Located in Kirribilli, short 5-minute walk from Milsons Point train station and Milsons Point ferry, Please note; STRICTLY NO PARTIES OR SOCIAL GATHERINGS. This is a quiet building. Any breech will result in immediate eviction. If you think you may be noisy after 10pm please choose another listing.

New York Style Loft in Sydney

Indulge in urban living at its finest in Woolloomooloo! Our 2-bed, 2-bath New York Style loft offers soaring ceilings, skylights, and indoor-outdoor living. Just minutes from Pitt Street Mall, Potts Point, Woolloomooloo Wharf, and the Opera House, you will find yourself a stones throw away from the city's best restaurants and bars. With a central marble counter for entertaining, it's the epitome of Sydney chic. Easy access to Kings Cross and Town Hall Stations. Book now for a unique city stay!

Light-Filled Designer Terrace | Darlinghurst | CBD

Step into a light-filled, architect-designed terrace in the heart of Darlinghurst. A full wall of north-facing glass and seamless indoor–outdoor flow create a calm, design-led space perfect for relaxing or exploring the city. New fully ducted air-conditioning (in April 2026) Polished concrete, high ceilings and warm, curated interiors give a modern, feel, while sliding glass doors open a courtyard framed by greenery. Perfect for couples, small families or work stays looking for a stylish base"

Inner city cottage hideaway

The best of both worlds: Inner city cottage in a quiet subtropical oasis. A secure house with all the comfortable mod-cons you need & very close to all Sydney city has to offer. Staying here feels like a private refuge which is airy, open and steeped in green surrounds whilst being a perfect base for exploring hip Redfern and Inner Sydney. Redfern Station is a 5 min walk away, 10 to Central, and moments to beautiful parks, shops, bars & restaurants of Redfern. Airport is 12mins by train.

Tree Top Apartment

Nestled in the top of an Historic Morten Bay Fig This light and airy 5th story north facing apartment is beautifully furnished and is perfect for a Sydney stay. Reverse cycle air-conditioned With European Appliances this chefs kitchen is stocked with everything you will need to cook with or there is a supermarket, gourmet takeaway and Fine Wine shop just across the road. With on Site parking and Pets allowed (some strata requirements) come and enjoy Lizzy Bay. Minutes walk to Restaurants.

Luxury Woolloomooloo waterfront

Kick back and relax in this calm, stylish space. Enjoy the gentle sounds of the twinkling yacht masts in the breeze. Perfect views of the Sydney skyline across the Botanical Gardens from all windows. This luxurious 1 bedroom apartment is your retreat getaway, with open plan living, kitchen and dining space. Enjoy a stroll along the waterfront to the Opera House, or savour a long lunch at one of the iconic restaurants right downstairs, on the Woolloomooloo Finger Wharf PID-STRA-94964

Sydney City Penthouse, vast City & Harbor Views

Float above a panorama of Sydney City and its Harbor in this 180sqm large, beautifully designed penthouse. Its a free standing house built on top of a flat roof, in Sydney’s best location. You land in the heart of Sydney with restaurants, cafes, bars, museums, parks, even the Opera and tourist attractions at your door step. Recharge, rewind and feel right at home in this unique Australian designer home with expansive and luxurious interiors, high ceilings, touches of Australian art.

My City Cocoon

Beautiful 2 bedroom apt in Darlinghurst with amazing city views. Great deck with indoor/outdoor living space. Quiet and private. Entertain at home or enjoy the restaurants, bars, and theatres close by. Close to the city and to the buzz of Darlinghurst, Surry Hills, Potts Point, Oxford St and Kings Cross. Walking distance to the SCG and Allianz Stadium. PLEASE NOTE - there is no lift. On request - parking spot in secure garage. On request - dogs welcome, non-shedding, up to 10kg.

Unique studio at Historic Wharf

Stunning studio apartment in the renowned Woolloomooloo Wharf built in 1915. Its beautiful views over the water and Potts Point are key, but this studio has everything you need for a city visit or a staycation. Conveniently placed just minutes to Potts Point and within walking distance to all of Sydney's main attractions: Botanic Gardens, Opera House, Harbour Bridge, Art Gallery NSW, Museum of Contemporary Art and the CBD. No parking Early check in or late check out (if available): $50

Charming Terrace Home @Great Location+Parking+BBQ

Our charming historic Victorian terrace home is fully equipped and in a fantastic location close to all Sydney offers. Located in the heart of vibrant Darlinghurst, you’ll be surrounded by cafés, galleries and theatres. Enjoy a stroll through Hyde Park to the CBD or take in harbour views from the Royal Botanic Garden and Opera House. Dining hotspots in Potts Point and Kings Cross are nearby, with Bondi Beach and Watsons Bay just 15 minutes away. Easy access to bus and train stations.

Designer house in quiet street on city doorstep

Located in a quiet and historic East Sydney laneway, this ultra-modern house is around the corner from Stanley St eateries and within walking distance of iconic Sydney landmarks, St Vincent's Hospital and the CBD. Surrounded by historic 1850s terraces, the house is on two levels with good security. The bedrooms are downstairs, with a light and airy open-plan living area upstairs flowing onto a deck with a gas barbecue. Resident parking permit available on request per night of stay.