Vacation rentals with a pool in Woolloomooloo

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Woolloomooloo

  • Total vacation rentals

    Explore 70 vacation rentals in Woolloomooloo

  • Nightly prices starting at

    Woolloomooloo vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,220 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Woolloomooloo vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woolloomooloo rentals

  • 4.9 Average rating

    Woolloomooloo stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Woolloomooloo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
A spacious balcony is presented, featuring modern outdoor seating and ornamental plants. Expansive views of the city skyline are visible in the background, with notable buildings and greenery adding to the backdrop under a clear blue sky.
Apartment in Darlinghurst
4.82 out of 5 average rating, 149 reviews

Stylish, Spacious, Spectacular Views Parking & Bbq

Beautifully furnished, open plan and newly renovated 2 bedroom apartment with amazing uninterrupted views of the city, harbour and bridge around to Kings Cross/Potts Point. Living areas open onto a wrap around balcony with sun all day. State of the art kitchen with hidden cupboard laundry (washer and dryer). Amazing vista from all living areas and both bedrooms. Balcony is perfect for entertaining or an intimate afternoon cocktail. Or enjoy the pool, spa sauna on the ground floor. Parking.

Top guest favourite
A private balcony offers outdoor dining with a table set for two, accompanied by vibrant views of the water and distant city skyline. Lush greenery frames the scene, while tranquil blue waters reflect the clear sky.
Condo in Mosman
4.98 out of 5 average rating, 192 reviews

Absolute Harbourfront Apartment with Fabulous Panoramic Views

Magnificent piece of paradise at the waters' edge. Heart stopping views from every room (Guest 2017) Bright & sunny, idyllic waterfront sanctuary Separate home office All linens and unit professionally cleaned Alfresco balcony perfect for drinks/meals BBQ dining, sun lounges, harbour pool Onsite parking: max. car height 1.7 metres Bus & ferry close Fireworks often seen, spectacular on New Year's Eve & Australia Day Peaceful by day, stunning by night Come and chill out – you won't want to leave!

Guest favourite
A cozy seating area features two plush armchairs positioned near a large window, providing unobstructed views of the ocean and cliffs. A small side table holds two glasses of wine, and a potted plant adds a touch of greenery.
Apartment in Vaucluse
4.96 out of 5 average rating, 128 reviews

Stunning 1bdr w/ Amazing View

Bright and airy one bedroom apartment nestled on top of Diamond Bay Cliffs with breathtaking ocean views. The stunning view overlooking the cliffs and the soothing sound of waves, provide an incredible connection to the ocean from awe inspiring sunrises to frolicking whales throughout the day. Relax with a wine or coffee in this beautifully styled home surrounded in comfort and serenity. Take a dip in the pool overlooking the ocean or take a walk along the cliff walkway. Free street parking

Guest favourite
Condo in Wynyard
4.95 out of 5 average rating, 120 reviews

urban serenity: quiet stay in central Sydney

Welcome to your perfect Sydney getaway! Located in the vibrant heart of the city, our stylish apartment offers a blend of comfort, convenience, and luxury, making it the ideal base for both business and leisure travelers.This beautiful apartment features open-plan living, contemporary furnishings, and large windows that flood the space with natural light. Whether you’re unwinding after a day of exploring or catching up on work, the space is designed for both relaxation and productivity.

Top guest favourite
A modern living space showcases a well-furnished area with a comfortable lounge chair, small side table, and a textured rug beneath. A stylish kitchen is visible in the background, illuminated by soft lighting. Green plants add a fresh touch near the window, enhancing the vibrant atmosphere.
Apartment in Potts Point
4.99 out of 5 average rating, 159 reviews

Stunning One Bedroom Art Deco Apartment

A gorgeous apartment on the border of Elizabeth Bay and Potts Point, one of the most vibrant and sought after areas to live in Sydney. The apartment is completely renovated and stylishly furnished with timber floors ,new kitchen and bathroom. Located on the 4th floor of an iconic Art deco building overlooking the stunning pool and manicured gardens which are the perfect space for entertaining and relaxing after a day exploring Sydney. The building has security access and 2 lifts.

Guest favourite
Apartment in Darlinghurst
4.85 out of 5 average rating, 982 reviews

Central l Pool l Rooftop Harbour Views

My “small” one bedroom apartment is centrally located to every area of the inner city, sprinkled with cafes, parks, bars and restaurants. This 1930's art deco building has a lift and an amazing rooftop terrace with pool and fantastic views of Sydney harbour. If you have an early flight you’re welcome to drop off your luggage earlier and make use of the shower and bathroom in my massage studio next door in 502. This service is also available for luggage storage after check out.

Top guest favourite
Apartment in Surry Hills
4.98 out of 5 average rating, 129 reviews

Hyde Park Tree-Top Views

A home away from home Located in Sydney CBD in Hyde Park Plaza - on the corner of Oxford st. and College st. Next to museum train station. You could not get a better location in the city. 333 bus to bondi , bottle shop, cafes just downstairs. This one bedroom unit is offering a really comfortable stay with excellent views. Perfect for business or a few nights' stay away to recharge but be aware of city noise ! If you have any requests please don’t hesitate to let me know.

Guest favourite
A rooftop pool with clear blue water provides sweeping views of Sydney's skyline, including notable landmarks such as the Sydney Tower and the bustling harbor. The surrounding area features modern buildings and green spaces, creating a vibrant urban landscape.
Apartment in Potts Point
4.87 out of 5 average rating, 324 reviews

Contemporary Potts Point Apartment with a Rooftop Pool

Large floor-to-ceiling windows welcome the Sydney sunshine in this stylish apartment furnished with chic, modern amenities. On the roof, take in views of Sydney Harbour and the Opera House as you float in the pool or dine on the deck. We're in the centre of Potts Point close to famous restaurants and shops in the area and 12 mins walk on the same street to trains. The studio contains many modern conveniences and gadgets from espresso machine to Google home and Sonos sound.

Guest favourite
A tranquil view is presented from the outdoor pool area, showcasing a curvy pool reflecting the twilight sky. Lush greenery surrounds the space, and adjacent to the pool, a stylish house offers expansive glass doors leading into the interior, creating a seamless indoor-outdoor connection.
Home in Seaforth
4.84 out of 5 average rating, 154 reviews

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!

Superhost
Apartment in Elizabeth Bay
4.82 out of 5 average rating, 212 reviews

Stylish Harbourside Apartment in Elizabeth Bay

Family-friendly Elizabeth Bay apartment with harbour views, pool & secure parking. Bright sunlit interiors with greenery in every room, premium bedding & full kitchen with German appliances. Enjoy Apple TV, high-speed WiFi & lift access in a secure building. Steps to Elizabeth Bay Marina, Macleay Street cafés & Kings Cross Station for easy Sydney access. Perfect for families wanting comfort, safety & convenience by Sydney Harbour.

Superhost
A bright living area featuring a textured white sofa with decorative cushions and a custom organic-shaped coffee table. A small dining table for two sits beside large windows, offering panoramic views of the harbor. An art piece hangs on the wall, adding a splash of color.
Apartment in Elizabeth Bay
4.87 out of 5 average rating, 125 reviews

Chic Sydney Stay: Water Views & Rooftop Pool

Discover Sydney in style! Experience our hotel-style room in Elizabeth Bay, a harbour-view haven in prestigious real estate. Enjoy the sun-drenched rooftop pool, gourmet cafes, and scenic parkland. With an unbeatable location & luxurious amenities, this apartment, featuring quirky décor adding a touch of elegance, is the perfect base for exploring Sydney's vibrant cityscape. Book now for urban charm, comfort, and convenience!

Superhost
A panoramic view of the sparkling harbor is captured, featuring a collection of sailboats positioned on the calm water. Lush greenery and modern buildings frame the scene, under a clear blue sky with scattered clouds, highlighting the vibrant coastal atmosphere.
Apartment in Potts Point
4.79 out of 5 average rating, 210 reviews

Light Filled Studio On Trendy & Vibrant Macleay St

Stylish naturally lite studio in the center of chic Macleay Street. With well renowned restaurants and cafes at your door step this makes for a great place to stay. Just a short walk to Hyde Park, CBD and the astounding sites of Sydney Harbour this studio offers a magnificent lifestyle experience for those seeking a stylish stay in the heart of what is unquestionably one of the world's foremost entertainment precincts.

Popular amenities for Woolloomooloo rentals with a pool

When is the best time to visit Woolloomooloo?

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Avg. price$262 CAD$259 CAD$220 CAD$199 CAD$189 CAD$199 CAD$192 CAD$213 CAD$223 CAD$230 CAD$241 CAD$289 CAD
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