Woolloomooloo holiday homes

We found 474 holiday rentals — enter your dates for availability
Discover a selection of 22 apartments and other holiday rentals in Woolloomooloo that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a hot tub. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find the best place to stay - Woolloomooloo

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Woolloomooloo

Why visit Woolloomooloo

  • Harbour views: Enjoy scenic vistas of the picturesque harbour and experience the charm of Woolloomooloo’s waterfront.
  • Iconic Wharf: Visit the renowned Woolloomooloo Wharf for a blend of local culture, history, and delightful urban vibes.
  • Historic streets: Wander along Brougham and Dowling Streets, taking in the unique architectural charm and vibrant local scene.
  • Charming cafes and boutiques: Discover an array of quaint cafes and boutique shops that offer a taste of local lifestyle.
  • Urban parks: Relax in the suburb's inviting urban parks, perfect for leisurely strolls and outdoor enjoyment.

Top attractions in and around Woolloomooloo

Woolloomooloo in Sydney offers a delightful blend of culture, romance, and lively urban experiences. Explore its charming urban parks, scenic streets, and the picturesque harbor, perfect for city and outdoor enthusiasts. Don't miss a visit to the iconic Woolloomooloo Wharf, where the local vibe and history come together in a uniquely enchanting way for every traveller.

  • Woolloomooloo Wharf: This vibrant marina offers a unique blend of adventure and relaxation, with stunning views, waterfront dining, and opportunities for outdoor activities, all set against a backdrop of historic architecture.
  • Circular Quay: Just a short stroll away, this bustling harbour provides picturesque scenery, perfect for enjoying the waterfront atmosphere and watching ferries come and go.
  • Sydney Opera House: A world-renowned cultural icon, this architectural masterpiece hosts a variety of performances and events, contributing to the rich artistic landscape of the area.

Things to do recommended for couples

Discover romantic Woolloomooloo with scenic harbour views and intimate dining experiences. Enjoy a leisurely stroll along the boardwalk, savour local flavours, and immerse in Sydney’s vibrant arts scene. Perfect for a couple's retreat from New Zealand, blending adventure and relaxation.

Things to do recommended for families

Families visiting Woolloomooloo can enjoy local waterfront dining and a stroll through the historic Finger Wharf, with plenty of parks and interactive exhibits nearby to keep the kids entertained.

Things to do recommended for groups

Experience the thrill of the Sydney Speedway, located 19km from Woolloomooloo. Gather your mates for an adrenaline-pumping day of motor racing amid the vibrant sports and adventure atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Woolloomooloo

Regardless of whether you're journeying as a group, with family, alongside your furry companions, or considering an extended stay, ensure you select the appropriate filters to match your priorities. Here are some Vrbo booking pointers tailored for you.

  • Traveling to Woolloomooloo with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for group gatherings. Thankfully, you can use filters on Vrbo to find all these options and more.
  • Traveling to Woolloomooloo with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woolloomooloo: For many, a family holiday simply isn't complete without their furry friend tagging along. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly options include feeding bowls and beds, so everyone will feel right at home.
  • Planning for a long term stay visiting Woolloomooloo: If you're after holiday rentals offering monthly deals, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on month-to-month stays. You might also want to include extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Woolloomooloo

Woolloomooloo, a vibrant suburb of Sydney, offers a delightful blend of culture and romance. Stroll along Dowling Street to discover charming cafes and boutiques, or visit the iconic wharf by Woolloomooloo Bay for stunning views. The historic Brougham Street is perfect for a leisurely walk, while the story building adds a unique architectural charm. Whether you're seeking a friendly atmosphere or a romantic getaway, Woolloomooloo promises an unforgettable experience.

  • Sydney: Sydney, a vibrant metropolis, offers an enticing blend of urban excitement and cultural heritage. Nestled within the city, Woolloomooloo provides easy access to Sydney's rich tapestry of theatres, music concerts, and operas, creating memorable experiences for culture, entertainment, and romance seekers. Visitors can explore a mix of beaches, family-friendly shorelines, and historical monuments that dot the landscape, making Sydney a captivating destination.
  • Sydney Central Business District: Just 1km away from Woolloomooloo, the Sydney Central Business District is a bustling neighbourhood that pulses with energy. This area is renowned for its cultural attractions and entertainment venues, including theatres, music concerts, and operas. A short stroll reveals stunning landmarks such as marinas, harbours, and iconic monuments, offering a dynamic urban experience that blends work and play seamlessly.
  • Darling Harbour: Located 2km from Woolloomooloo, Darling Harbour is a lively neighbourhood that combines waterfront charm with a rich cultural scene. With an array of theatres, music concerts, and operatic performances, it promises an engaging experience for lovers of culture, entertainment, and romance. The vicinity is adorned with scenic marinas, harbours, and striking monuments that capture the essence of Sydney’s coastal allure.

Best time to go to Woolloomooloo

If you're planning a trip to Woolloomooloo, it's a good idea to check both the weather and property rates. The warmest month is January.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January73.4°F (23.0°C)Light RainMostly Sunny
February72.7°F (22.6°C)Light RainMostly Sunny
March70.9°F (21.6°C)Light RainMostly Sunny
April66.4°F (19.1°C)Light RainMostly Sunny
May61.2°F (16.2°C)No Rain (Dry)Mostly Sunny
June57.2°F (14.0°C)Light RainMostly Sunny
July55.9°F (13.3°C)Light RainMostly Sunny
August57.2°F (14.0°C)No Rain (Dry)Mostly Sunny
September61.2°F (16.2°C)No Rain (Dry)Mostly Sunny
October64.6°F (18.1°C)Light RainMostly Sunny
November67.6°F (19.8°C)Light RainMostly Sunny
December70.3°F (21.3°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

Looking to save on your next escape? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, simply use our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a convenient platform to plan new adventures, pick up from where you last stopped, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently Asked Questions

When is the best time to visit Woolloomooloo for a holiday rental?

February is the prime time to visit Woolloomooloo, with warm summer weather and vibrant energy drawing holidaymakers to this beautiful coastal area. This peak season, which spans from December to February, offers an array of outdoor activities, from relaxing on the stunning beaches to exploring the nearby Royal Botanic Garden. Visitors can enjoy temperatures averaging between 20 to 30 degrees Celsius, making it great for sightseeing and leisurely strolls along the picturesque waterfront.


As the summer sun shines brightly, Woolloomooloo comes alive with events, festivals, and a bustling atmosphere that caters to all types of travellers. February, in particular, often sees a mix of locals and tourists, creating a lively yet welcoming vibe.


If you're looking for a more budget-friendly option, consider visiting in July, the low season. While temperatures can dip to around 10 to 15 degrees Celsius, this quieter month allows for a more relaxed experience, enabling you to explore local cafés, art galleries, and the unique character of the area without the crowds.


Ultimately, the best time to book a holiday rental in Woolloomooloo will depend on your preference for vibrant summertime activities or a peaceful winter retreat.

What are the top attractions in Woolloomooloo, New South Wales, Australia?

Woolloomooloo is a vibrant area known for its picturesque waterfront and rich history. One of the top attractions is the iconic Woolloomooloo Wharf, which features a range of dining options and stunning views of the harbour. The nearby Royal Botanic Garden offers a serene escape with beautifully landscaped gardens and walking paths, making it an ideal spot for a leisurely stroll or a picnic.


Additionally, the historic Finger Wharf is a popular destination, showcasing a mix of contemporary apartments, restaurants, and art galleries. Close by, visitors can explore the Art Gallery of New South Wales, which houses an impressive collection of Australian and international art. For those interested in history, the area is also near the historic site of the former Woolloomooloo Gaol, adding a cultural touch to the neighbourhood's charm.

Are all fees included in the Woolloomooloo holiday homes prices shown on Bookabach?

Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

Are there any Woolloomooloo holiday homes with parking?

Bookabach offers a wide selection of holiday homes in Woolloomooloo with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

Are there any discounts for Woolloomooloo holiday homes?

You can find great discounts on holiday homes in Woolloomooloo on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I change or cancel my Woolloomooloo holiday home booking on Bookabach?

To find Woolloomooloo holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.

Can I find long-stay holiday homes in Woolloomooloo?

A long-stay holiday home in Woolloomooloo is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Can I plan a group trip on Bookabach?

Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.

How early should I book a Woolloomooloo holiday home?

Book your Woolloomooloo holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.

How much does it cost to rent a holiday home in Woolloomooloo?

Prices for holiday homes in Woolloomooloo vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Woolloomooloo to more spacious homes.

What can I expect from Bookabach customer service and Bookabach Care™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

What is Bookabach Care™ and how does it work?

Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

Why should I join Bookabach as a host?

Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More Holiday Ideas