
Vacation rentals with a pool in Woolloomooloo
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woolloomooloo
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Luxury Apartment Overlooking City and Darling Harbour
Feel the excitement of being only an elevator ride away from harbour-side activities. Admire walls filled with edgy and captivating art, and unwind on a comfy leather couch. Have nightcaps on the balcony and sleep in bedrooms with city skyline and Harbour views. We know you will feel at home with super comfortable modern light and cozy bedrooms, with built-in wardrobes and TVs. Google Chrome is also available on the Main TV in the lounge room. I'm sure you'll love coming back and unwinding after a day or night of enjoying everything Sydney offers. You'll not want to leave!
Chic Potts Point Studio – Sydney’s Hidden Gem Stay
Wake up in the heart of one of Sydney’s most vibrant neighbourhoods, surrounded by award-winning cafés, renowned restaurants, & hidden local gems. Start your day with a refreshing dip in the pool, then enjoy a scenic stroll to the Royal Botanic Gardens, CBD, or Opera House. This light-filled 22sqm studio in Potts Point is stylish & thoughtfully designed for comfort, with every detail carefully considered. Perfect for solo travellers, business stays, or couples seeking an R&R Sydney city escape.

Stunning Unit City Harbour Views + Parking +BBQ
Beautifully designed and styled, open plan kitchen/lounge/dining with wrap around balcony facing north west, attracting the sun all year round. 2 stunning bathrooms. White washed floor boards throughout, painted in neutral colours creating a natural summer relaxed feel. The mood lighting enhances the night view/ambience of the apartment. State of the art kitchen, marble bench top, fabulous breakfast bar. Panoramic views of the City, Harbour Bridge, Sydney Harbour, Kings Cross, Potts Point.

Sensational Hyde Park Oasis • Balcony • Pool & Gym
Unwind in our stylish CBD oasis - a newly renovated modern studio apartment in the heart of Sydney. This sunny inner-city sanctuary features luxury amenities including a queen bed with quality linens, chic bathroom with complimentary toiletries, washing machine, full kitchen, Nespresso machine, tea, free Wi-Fi, and Netflix. Enjoy amazing Oxford Street views while being in walking distance to the Opera House, Art Gallery, Sydney Tower, and Royal Botanic Gardens. Perfect for your Sydney stay!
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!

Best Sydney Views from Potts Point + Rooftop Pool
Immerse yourself in the heart of Potts Point with show-stopping views of Sydney Harbour and its surroundings—both from your apartment and the stunning shared rooftop pool. Located in the Gemini complex, you'll be within walking distance to the CBD, Kings Cross Station and some of the city's best shopping and dining. Beautifully outfitted with trendy furnishings and a unique selection of books and artefacts, you'll have everything and more to feel stylishly content at this home away from home.

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

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.

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.

Luxury Garden Cottage Retreat - Romantic & Restful
Arriving through antique gates, wander down wisteria covered walkway to your home away from home. Outdoor tiled undercover area with dining/living space, lit in evenings with silk lanterns invite you outside for a special occasion. Light-filled cottage, open plan living/dining area. Bedroom boasts plush queen bed for a blissful nights' sleep. Bathroom invites indulgence with a rainforest shower. Fully equipped kitchen with washing machine. Thoughtful touches throughout.

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!
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

Gordons Bay Vista ISYD

Spacious 4BR Waterfront House w/pool in Sth Coogee

Bundeena Base Art House Sea View Solar Heated Pool

6BR Stunning Waterview with Private Pool in Mosman
Condo rentals with a pool

Darling Harbour Breeze with car park

Quiet Living•Family Friendly•Netflix•Free Parking

Beautiful One Darling Harbour Apt

Rosebery 2BR| Free Parking | 8 min to Woolworths

Lovely One Bedroom + Study with Infinity Pool

Modern apt in Central Sydney: Harbour Views & Pool

Waterfront Apartment on a quiet cul-de-sac

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

Iconic Harbour view from Potts Point studio

Luxury Woolloomooloo waterfront

Spectacular Suite, Bridge & Water views, The Rocks

Absolute Best Location - Inner City Luxury Heaven.

Treetops, King Bed, Car Space

Light filled apartment w balcony, pool & parking

Harbourside Retreat on Iconic Finger Wharf

Cliffside Escape w/ Pool & Panoramic Ocean Views
When is the best time to visit Woolloomooloo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 CAD | $255 CAD | $216 CAD | $195 CAD | $186 CAD | $195 CAD | $189 CAD | $209 CAD | $219 CAD | $226 CAD | $237 CAD | $284 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 |
Quick stats about vacation rentals with a pool in Woolloomooloo

Total vacation rentals
Explore 60 vacation rentals in Woolloomooloo

Nightly prices starting at
Woolloomooloo vacation rentals start at $96 CAD per night before taxes and fees

Verified guest reviews
Over 3,020 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 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!
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