House vacation rentals in Woolloomooloo

Urban Farmhouse Flair—Surry Hills Terrace Serenity

This luxe terrace in Surry Hills strikes the perfect balance between industrial & rustic charm. Footsteps from the vibrant dining and entertainment precinct of Crown Street, it offers everything you need right on your doorstep. Inside, the home features three bedrooms with its own ensuite. The living and dining areas are designed for year-round comfort, enhanced by a striking hanging fireplace. Enjoy the rooftop patio, perfect for soaking up Sydney’s sunny days or savouring cool evening breezes.

Family · Location · Cleanliness

Elegant 3-Bed Terrace | Parking Included

Stay in the Heart of Surry Hills! Welcome to your stunning three-story terrace on Crown Street, the heartbeat of Sydney’s coolest neighborhood. Surrounded by buzzing cafes, restaurants on every corner, trendy bars, and boutique shops, you’ll feel the vibrant energy at every turn. With public transport at your door and the CBD just a 20-minute stroll away, everything you need is within reach. Live like a local, savor the flavors, and experience the best of Surry Hills right outside your doorstep!

Value · Family · Kitchen

Modern retreat in prime location

Conveniently located in the heart of Rozelle, this modern retreat offers a perfect blend of trendy cafes and boutiques on Darling Street and the tranquille Bay Run, Dawn Fraser Baths and newly opened Rozelle Parklands. A 10-minute bus ride takes you to the center of Sydney, providing easy access to iconic landmarks like the Opera House and Harbour Bridge. Whether you're exploring the city or unwinding in the peaceful surroundings of Rozelle, this is the perfect base for your Sydney adventure.

Location · Family · Amenities

Little Edie charming architect designed cottage

A gorgeous, free-standing two level stables converted into a chic, fully self contained cottage in the heart of Paddington's leafy streets, Little Edie is an architecturally designed jewel box for grown ups providing the perfect place to rest and relax during your next visit to Sydney. Centrally located, it is two blocks from Oxford Street's boutiques, bars, restaurants, public transport and just a few minutes from the city, sports stadiums and glorious beaches. We love giving local tips too!

Location · Family · Air conditioning

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.

Location · Family · Pool

Harbour Terrace 2BR Central 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 ✅

Value · Location · Heating

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.

Value · Family · Parking

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.

Location · Family · Pets

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.

Family · Value · Indoor spaces

Terrace House w Incredible Garden Near Kings Cross

Stay in the heart of Darlinghurst, just moments from Hyde Park, Oxford Street, Surry Hills, Sydney CBD, the Royal Botanic Garden, Circular Quay, the Sydney Opera House, and Harbour Bridge. This spacious three-storey terrace sleeps up to 8 guests with 3 bedrooms, 2 bathrooms, plus two additional sleeping spaces in the living area: a standard sofa and a single pull-out sofa chair bed. Enjoy a private courtyard and easy access to Sydney's best cafés, dining, and nightlife.

Location · Family · Condition

World Class Villa HarbourView Private Beach Manly

Sitting in an exclusive harbourfront cul-de-sac, you will have a great time with your family and friends in this resort style house. Convenient and close to the shops, restaurants, beaches and reserves. Plenty of local spots for having family time with the children. Spectacular harbour and city skyline view, grand entertainment area and pool cabana, Manhattan stylish courtyard in holiday vibes. We are looking forward to your reservation for a relaxing getaway!

Location · Value · Pets

Billionaire's Harbour Retreat in Woolloomooloo

Experience one of Sydney's most exclusive private residences in the heart of Woolloomooloo. This architect-designed Victorian terrace blends heritage charm with five-star luxury, moments from the CBD, Harbour and Potts Point. Enjoy premium finishes, smart-home technology, a private courtyard and secure garage. An identical neighbouring residence is also available upon request via a separate booking for larger groups (14 people in total).

Location · Nearby · Hospitality