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Vacation rentals with a pool in Woollahra

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Woollahra

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

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Top guest favorite
A panoramic view displays the Sydney Harbour, featuring the iconic Sydney Opera House and Sydney Harbour Bridge. The landscape includes a mix of historic and modern buildings, with the water reflecting sunlight. The vibrant atmosphere is enhanced by boats navigating the harbour.
Apartment in The Rocks
4.96 out of 5 average rating, 345 reviews

World Class location+Pool, Spa+Harbour Bridge View

A snapshot is worth a thousand words, but experiencing these panoramic views of Sydney in person is priceless! Experience SYDNEY THROUGH OUR EYES From sunrise painting the sky with hues of pink and purple, to ferries gliding beneath the Sydney Harbour Bridge, vibrant locals that bring the night to life, this is just a glimpse into the magic that awaits outside our doors. Wake up to some of Sydney’s most iconic treasures right outside your window, and let the city's beauty unfold before your eyes

Top guest favorite
A rooftop spa invites relaxation with bubbling water, framed by sleek railings and wooden decking. The horizon reveals a scenic view under a partly cloudy sky, enhancing the serene atmosphere of this elevated retreat.
Apartment in Darlinghurst
4.99 out of 5 average rating, 131 reviews

Sensational Hyde Park Oasis w/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!

Top guest favorite
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, 189 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!

Top guest favorite
Apartment in The Rocks
5 out of 5 average rating, 159 reviews

Supreme Sydney Rocks Suite + Spectacular Pool View

Wake up to Sydney’s harbourside magic. Step into the heart of The Rocks - moments to our panoramic Circular Quay and the breathtaking Opera House. Walk to George Street or Barangaroo where Sydney's best bars & restaurants are all waiting to be experienced. Find in house dining or stroll to public transport for ferries to visit Manly or Taronga Zoo. Indulge in sophistication and immerse yourself in the vibrant cityscape. Note: the balcony and view are located upstairs with the shared pool.

Guest favorite
A view from the window reveals Sydney's harbour, featuring boats on the water and distant greenery. A small hanging terrarium and a stack of books are visible on the windowsill, complementing the scene of natural light and soft clouds.
Apartment in Elizabeth Bay
4.85 out of 5 average rating, 499 reviews

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, trendy restaurants and hidden local gems. Begin your morning with a refreshing dip in the outdoor pool before strolling to the Royal Botanic Gardens, CBD or Opera House. This light-filled 22sqm Potts Point studio is stylish, modern and designed for comfort, with every detail thoughtfully considered. Perfect for solo travellers, business trips or couples seeking a relaxing Sydney city escape.

Guest favorite
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, 104 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

Top guest favorite
A bright sleeping area features a spacious bed adorned with neutral bedding. A minimalist design is complemented by soft pillows and a TV mounted on the wall. Large windows frame stunning views of Sydney Harbour and The Harbour Bridge, enhancing the natural light in the room.
Apartment in Elizabeth Bay
4.93 out of 5 average rating, 745 reviews

Iconic Sydney Views

A newly renovated studio apartment, with iconic Sydney views of The Harbour Bridge, The Opera House and Harbour. With a queen sized bed, my apartment is perfect for a couple, a solo traveller or business person, looking for accommodation that is beautiful, clean, convenient and with unparalleled comfort. Located in the heart of Potts Point you are moments away from all of Sydney's attractions and local hotspots. The perfect place for your stay in Sydney! (No Parking available on site)

Guest favorite
Apartment in Milsons Point
4.87 out of 5 average rating, 389 reviews

Harbourside App w Pool & Parking *Remedial work*

*Please note reduced rate due to remedial work Feb – Dec 2026* A comfortable apartment in the best location! Right next to the beautiful northern parkland of Sydney Harbour Bridge near Luna Park Sydney. You’ll be in the middle of the delightful Kirribilli village. The train is a skip away and only one stop to the city. Parking included. The following inconveniences are anticipated: Scaffolding around the building Inaccessible balcony Construction noise during weekdays (8am – 4pm)

Top guest favorite
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 King's Cross
4.99 out of 5 average rating, 139 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 favorite
The studio showcases a cozy sleeping area featuring a wooden bed with a patterned duvet. Flanking the bed are two bedside tables with lamps. A small dining table for two is set with plates and cups, complemented by modern chairs. Natural light filters from a nearby window.
Loft in Bondi Junction
4.75 out of 5 average rating, 111 reviews

Bondi studio, separate bathroom & pool

The studio is above the garage, separate from the house, with its own entrance. There's a toilet cubicle and sink in the studio, while your private bathroom with shower and another toilet is downstairs, accessed via the outside staircase. Starter supplies of tea, coffee, milk and sugar are provided. We're 10-15 minutes' walk from Bondi Junction train station, with several bus routes nearby. Close to beaches, Bondi Junction shopping and transport hub, bars, restaurants.

Guest favorite
A well-maintained exterior of a private residence is shown, featuring neatly trimmed hedges and tall conifer trees flanking a staircase. The white walls of the building contrast with the green foliage, while decorative balconies and large windows create a welcoming facade.
Guesthouse in Vaucluse
4.83 out of 5 average rating, 134 reviews

Apartment set in garden of elegant Vaucluse home.

Private apartment set in large garden of elegant Vaucluse home, a short stroll to cafes and shops, close to harbour beaches and on a bus route. Apartment is totally private and very quiet with own entrance. It comes with fully equipped kitchen. It also has a Nespresso coffee machine, with complimentary teas and coffee. The apartment has all mod cons including reverse cycle air conditioning, TV, Bluetooth speaker, wifi and a good hairdryer!

Superhost
A bright sleeping area is featured, showcasing a spacious bed adorned with a textured blanket and colorful decorative pillows. A view of the ocean is visible through a large window, while folded towels and a small plant add a touch of comfort.
Apartment in Bondi
4.83 out of 5 average rating, 231 reviews

Pacific Views Bondi

Bright ocean-facing private studio with sweeping views. Enjoy a comfortable sleep on a new mattress with quality bedding, a fully equipped kitchen, and a bathroom stocked with essentials and cotton towels. Just a short walk to iconic Bondi Beach, with buses outside the building for easy access to Sydney’s sights and plenty of international eateries nearby. The building also has a communal rooftop pool (closed until February 15th).

Popular amenities for Woollahra rentals with a pool

When is the best time to visit Woollahra?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,959 GYDG$32,794 GYDG$32,377 GYDG$26,946 GYDG$24,857 GYDG$24,230 GYDG$20,470 GYDG$26,319 GYDG$25,901 GYDG$34,048 GYDG$32,586 GYDG$31,750 GYD
Avg. temp24°C24°C22°C20°C17°C14°C14°C15°C17°C19°C21°C23°C

Quick stats about vacation rentals with a pool in Woollahra

  • Total vacation rentals

    Explore 70 vacation rentals in Woollahra

  • Nightly prices starting at

    Woollahra vacation rentals start at G$4,178 GYD per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woollahra vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woollahra rentals

  • 4.8 Average rating

    Woollahra stays are highly rated by guests—averaging 4.8 out of 5!