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Holiday rentals with a pool in Woollahra

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Woollahra

  • Total holiday rentals

    Explore 60 holiday rentals in Woollahra

  • Nightly prices starting at

    Woollahra holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 810 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woollahra holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Woollahra rentals

  • 4.8 Average rating

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

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 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, 195 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!

ValueFamilyQuiet

Top Guest favourite
Guest suite in Cremorne Point
4.96 out of 5 average rating, 126 reviews

Opera House Views | Harbourfront Cremorne Point

Immerse yourself in Sydney as you wake to breathtaking views of Sydney Harbour, the Opera House and the filtered Harbour Bridge. Make yourself a cup of coffee or tea and watch the harbour come to life, as ferries begin crossing the water and, during cruise season, cruise ships sail into Sydney Harbour. Listen to the birds singing in the trees. Then enjoy a leisurely breakfast as you watch through the arched window — the harbour activity across the water and locals out for their morning walk.

LocationValueLong stay

Guest favourite
A spacious living area features a comfortable leather couch and a geometric coffee table. Bright wall art adds a modern touch, while large glass doors provide access to a balcony overlooking the city skyline. A television is mounted on a sleek entertainment unit.
Apartment in Pyrmont
4.98 out of 5 average rating, 270 reviews

Luxury Apartment Overlooking City and Darling Harbour

Experience the best of Sydney, with the harbour, iconic attractions, restaurants and nightlife just an elevator ride away. Relax in a stylish apartment with contemporary artwork, a leather lounge and a private balcony overlooking the sparkling city lights. Wake to stunning harbour and skyline views from the light-filled bedrooms, each with a TV and built-in wardrobe. Google TV is available in the lounge. I’m sure you’ll love returning after a day exploring Sydney. You may never want to leave!

LocationValueGetting around

Top Guest favourite
An indoor pool area is framed by large glass panels, offering a view of the iconic Sydney Harbour Bridge. Comfortable seating is positioned nearby, allowing for relaxation while enjoying the scenery. The space features elegant columns and subtle greenery, creating a soothing atmosphere.
Apartment in The Rocks
5.0 out of 5 average rating, 190 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.

ValueFamilyIndoor spaces

Superhost
A stylish living area is showcased, featuring a comfortable leather couch and a unique coffee table. Large windows provide sweeping views of the Sydney skyline, while a wooden cabinet and decorative lamp add character to the space. A ceiling fan completes the modern atmosphere.
Apartment in Potts Point
4.77 out of 5 average rating, 209 reviews

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.

LocationValueAccess

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, 131 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

ValueFamilyCleanliness

Guest favourite
Condo in Wynyard
4.95 out of 5 average rating, 124 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.

LocationFamilySleep quality

Guest favourite
Apartment in Darlinghurst
4.85 out of 5 average rating, 988 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.

FamilyValueDecor

Top Guest favourite
Apartment in Surry Hills
4.98 out of 5 average rating, 133 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.

LocationValueAmenities

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
4.83 out of 5 average rating, 159 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!

ValueFamilyOutdoor spaces

Guest favourite
A panoramic view captures the bustling skyline of Sydney, featuring tall buildings and distinctive architecture. The vibrant colors of flags line the waterfront, and the iconic Sydney Tower stands tall against a clear blue sky, complementing the serene water below.
Apartment in Pyrmont
4.9 out of 5 average rating, 324 reviews

Sydney Darling Harbour Sydney Views

Stunning views of City and Sydney's Darling Harbour. Bright and fresh sunny 2 bedroom + 2 bathroom apartment. HUGE - 130sq.metres of internal + very large balcony. Modern design and amenities. Restaurants, Bars, Convention Centre and Sydney CBD all at your doorstep​​. Transport - Ferry, Light Rail and Busses all adjacent to the building. Gym, Heated pool, Sauna and Spa Large Supermarket 50 metres away. Coffee and convenience store at the front entrance.

LocationValueView

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, 212 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.

ValueLocationDecor

Popular amenities for Woollahra rentals with a pool

When is the best time to visit Woollahra?

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Avg. price$282 AUD$233 AUD$211 AUD$193 AUD$182 AUD$149 AUD$136 AUD$175 AUD$172 AUD$226 AUD$217 AUD$211 AUD
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