House vacation rentals in Woolloomooloo

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Top-rated house rentals in Woolloomooloo

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Guest favorite

A staircase with wooden steps and a metal railing is framed by white brick walls and large windows above, allowing natural light to illuminate the space. The design features a blend of polished concrete and minimalist aesthetics, highlighting the industrial heritage of the property.

Home in Darlinghurst

4.9 out of 5 average rating, 115 reviews

Australia Architecture Award Winner Heritage House

You will be staying in a unique house that won the 2019 National Heritage Architecture Award. The house is tucked away in the quiet alleys of a residential area, amidst a blend of Georgian, Victorian terraces. The residence boasts lofty ceilings, custom finishes, and a touch of history, promising an exceptional living environment. Houses Awards: Alts + Adds Winner 2019; House in a Heritage Context Winner 2019; AIA NSW Awards (Heritage: Adaptive Reuse); Francis Greenaway Named Award Winner 2019

Top guest favorite

A charming cottage is nestled among vibrant greenery, featuring a stone pathway leading up to the front porch. The light-colored wooden exterior is complemented by a dark roof and well-maintained garden beds filled with pink flowers and leafy plants.

Home in Waverton

4.95 out of 5 average rating, 128 reviews

The Bath House - Cozy Luxe Garden Cottage near CBD

The Bath House – LOCATION & CHARM near stunning harbour views. Nestled in a peaceful garden, this charming self-contained cottage offers a unique bath experience and a romantic patio with fairy lights. Located in a historic precinct, just 500m from Waverton Station (3 stops to Sydney CBD). This boutique retreat has private access and is surrounded by the vibrant cafes and restaurants of Waverton/Kirribilli area. Only a short walk to Luna Park, the Harbour Bridge, Sydney Harbour and ferries.

Guest favorite

A wooden dining table with seating for four is positioned against a white wall, complemented by framed black-and-white artwork above. A floor lamp stands nearby, and a staircase with a textured runner is visible, enhancing the area’s minimalist design.

Home in Woolloomooloo

4.92 out of 5 average rating, 248 reviews

2 Bedroom Terrace In The Heart Of Woolloomooloo

- Harbour side location, easy stroll to cafes and bars ✅ - Free to use full sized tennis and basketball court 1 minute walk with 4 X tennis racquets and Basketball supplied ✅ - Playground for the kids ✅ - Award winning matress' with fresh high quality linen ✅ - Full kitchen with all essentials, coffee, tea etc ✅ - Each bedroom has 32" Smart TV with Netflix ✅ - Washer/Dryer combo with liquid supplied ✅ - Fresh Towels ✅ - Beautiful walkable location close to Opera house and botanic gardens ✅

Superhost

A fully equipped kitchen features modern appliances, including a large oven and refrigerator. The spacious island with bar seating provides a functional area for meal preparation and entertaining. Natural light streams through the windows, enhancing the bright, welcoming atmosphere.

Home in Millers Point

4.88 out of 5 average rating, 154 reviews

Heritage Terrace with City & Park on your doorstep

Experience the charm of Sydney’s history with a stay in this beautifully renovated apartment, the original home of Alfred Short, the builder of Shorts Terrace in the 1870s. This luxurious apartment has been meticulously updated to offer modern comforts while preserving its heritage character. Perfectly located in the heart of The Rocks, Barangaroo, and within walking distance of the CBD, it’s the ideal base to access all Sydney has to offer—whether you're in town for business or leisure.

Superhost

A row of heritage-listed terraces features classic sandstone facades, large windows with green shutters, and a welcoming entrance. The street is lined with parked cars, and the surrounding trees provide natural greenery to the historic neighborhood.

Home in Millers Point

4.87 out of 5 average rating, 107 reviews

Exclusive living in a Historic Home

With 180 degree views of Barangaroo and Balmain and a courtyard for enjoying afternoon drinks, this 3 storey home is fitted with all the modcons including smart TV, WIFI, luxury Egyptian cotton linen, air con, washer/dryer, marble kitchen, wooden floors, rain shower heads, customised wardrobes, a clawfoot bathtub and Victorian fireplaces. 5 min walk to Barangaroo, 10 mins to Circular Quay and CBD and around the corner from some of the best restaurants and bars that Sydney has to offer.

Superhost

A charming entryway is featured, with a bright blue door that adds a pop of color. Two large planters flank the entrance, filled with lush green plants. The façade showcases a mix of modern design elements, including decorative lighting and security bars on the windows.

Home in King's Cross

4.85 out of 5 average rating, 240 reviews

Collected/Places Woolloomooloo - The heart of Syd

Located in the heart of Sydney, this award-winning 3-bedroom, 2.5-bathroom townhouse blends modern comfort with stylish design. Features include luxe linens & ammenities, climate control, fully equipped kitchen & open-plan indoor & outdoor living. Located in Woolloomooloo, home to Australia's oldest pub, the house is just minutes to the best bars and restaurants, Sydney Harbour, Sydney Opera House, the CBD & transport with a direct line to Bondi. Ideal for a luxurious city stay.

Guest favorite

An open-plan living area features exposed brick walls that add character. A dark sofa with cushions is positioned across from a modern TV on a stand. Nearby, glass doors provide access to a private terrace, complemented by natural light illuminating the space.

Home in Darlinghurst

5 out of 5 average rating, 5 reviews

Sky & Stone – Luxury House in Darlinghurst

Welcome to Sky & Stone, an urban retreat that blends heritage charm with modern style in the heart of Darlinghurst. Enjoy exposed brick walls, soft lighting, and a cozy, curated interior. Sip coffee or wine on the sunny private terrace surrounded by greenery. Inside, relax in the open-plan living area, read in a quiet corner, or cook in the fully equipped kitchen. Upstairs, a plush bedroom offers hotel-style comfort and natural light. Ideal for couples, solo or business stays.

Guest favorite

A comfortable living area features light wood flooring and a cozy armchair. Sliding glass doors open to the backyard, inviting natural light. A small round table holds snacks and a plant, while a soft rug adds texture to the space.

Home in Mosman

4.95 out of 5 average rating, 138 reviews

Mosman retreat close to harbour

Take a ferry ride with a cup of coffee to the city, listen to the lions roar in the zoo with a French glass of wine in the garden are just few of the lovely activities while staying at our BnB. Staying in a historic home with modern finishes and comfortable provincial styling is the perfect base to explore the city of Sydney and return to a quiet retreat at night. Your French-Australian host will do their best to make sure your stay is comfortable and you will want to return.

Guest favorite

A spacious bedroom features a wooden bed with a light-colored comforter positioned next to a stylish area rug. Two leather recliners in a neutral tone are positioned to invite relaxation, while soft lighting and wooden flooring enhance the overall ambiance.

Home in Chatswood

4.88 out of 5 average rating, 162 reviews

Quiet Private Independent

Brand new, private very spacious bedroom with ensuite bathroom and a walk-in closet. Very quiet location close to Westfield Shopping Centre Chatswood (15 min) and only 5 mins to a Buss Stop. Direct trains to CBD. This property is presented to you with the highest level of hygiene and cleanliness, managed onsite. This place comes with the best features such as central air conditioning, a new kitchen, washing machine and high-speed Wi-Fi NBN network. No children under 12.

Superhost

A modern living area features a plush blue sofa, complemented by a light-colored armchair and a round coffee table. Lush indoor plants add greenery, while large glass doors lead to an outdoor space, allowing natural light to brighten the room.

Home in Surry Hills

4.86 out of 5 average rating, 22 reviews

Full AC | Filtered Water/Ice | Keyless | Sound Bar

→ Air Conditioned Bedrooms + Living Area (Heating and Cooling) → Keypad Entry → 110 Mbps Internet → Chefs Kitchen → Vitamix Blender → Quality Pots/Pans and Japanese Knives → Induction + Steam Oven → Filtered Water + Ice → Large Fridge/Freezer → Dishwasher → Washing Machine/Dryer → 55” Frame TV + Sound Bar → Nespresso + Stove Top Coffee → Bondi Wash Products → Children’s Playground → Netflix, Stan, Apple TV, Amazon → Awesome Local Pub - The Carrington (just steps away)

Guest favorite

A spacious living area is showcased, featuring a comfortable sofa and a round ottoman. Large floor-to-ceiling windows provide stunning ocean views, while natural light fills the room. A neutral color palette with light wood flooring enhances the airy atmosphere, inviting relaxation.

Home in Tamarama

4.94 out of 5 average rating, 138 reviews

Absolute Tamarama Beachfront on Bondi Coastal Walk

LOCATION LOCATION! No better LOCATION! Immerse yourself in the breathtaking beauty of Tamarama Beach, Sydney's exclusive coastal gem. Our Absolute Tamarama Beachfront provides direct access to the mesmerising ocean waves, just steps away. Relax on the full-sized balcony and enjoy uninterrupted views from the Bondi Coast Walk to Tamarama, Bronte, Clovelly, and Coogee. Experience Sydney's iconic eastern surfing coastline from our captivating holiday home.

Top guest favorite

The entrance features a welcoming doorway with a bold black door, framed by a light-colored wall. A modern light fixture illuminates the house number 263. Lush green plants in a pot add a vibrant touch to the entryway, enhancing the inviting atmosphere.

Home in Darlinghurst

5 out of 5 average rating, 19 reviews

Skyline on Forbes - 4 bedroom home Darlinghurst

Nestled in the heart of Darlinghurst, ‘Skyline’ on Forbes offers the ultimate inner-city lifestyle. With its prime location, this terrace is a seamless blend of heritage charm and urban convenience, placing you within walking distance of vibrant cafes, theatres, boutique shopping, the cultural buzz of Oxford Street and the CBD. Whatever the reason is for your Darlinghurst stay, you will find Skyline an ideal choice for a memorable and relaxing stay.