
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.

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.
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!

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

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.

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.

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.

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.

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.

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!

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.

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!

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
House rentals with a pool

Poolside oasis - outdoor living at its best

Coastal Zen Oasis with Saltwater Pool & Hot Tub

Cozy 2 bedrooms Grannyflat with air-con & pool

Gladesville By The Water

Salty Views on Cross St Bronte

Stunning 3 br home near beach with pool and sauna

Guest House in bush setting with use of pool

Sun drenched Art Deco apart with pool and garden
Condo rentals with a pool

Darling Harbour Breeze with car park

Quiet Living•Family Friendly•Netflix•Free Parking

Stylish 1BR suite with City-view & Balcony

Rosebery 2BR| Free Parking | 8 min to Woolworths

Lovely One Bedroom + Study with Infinity Pool

Modern apt in Central Sydney: Harbour Views & Pool

Sunny 1 Bedroom City Apartment with Rooftop Pool

Darling Harbour Apart Waterview near ICC and Star
Other vacation rentals with a pool

Potts Point Studio Oasis

Sydney Darling Harbour Sydney Views

Stunning View, Modern, Heart of City

Modern Harbour Retreat · Views · Design · Comfort

Luxury Woolloomooloo waterfront

Resort Style Apt with View & Car Space

Sky High@ Surry Hills 1 Bdrm /Walk to the City

Luxury Apartment Overlooking City and Darling Harbour
When is the best time to visit Woolloomooloo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 24 °C | 24 °C | 22 °C | 20 °C | 17 °C | 14 °C | 14 °C | 15 °C | 17 °C | 19 °C | 21 °C | 23 °C |
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