
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 €17 per night before taxes and fees

Verified guest reviews
Over 790 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Woollahra holiday rentals include wifi 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!
Top-rated rentals with a pool in Woollahra
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.
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!

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.

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

Spa Serenity Cottage with Private Pool & Spa
This is a Granny Flat located at the back of our property, with its own private entrance and complete privacy. The pool, spa, and backyard are exclusively yours, no one else shares these spaces. Just so you’re aware, we live in the main house at the front. While you may occasionally hear us, we’re very quiet and respectful of your space. Please respect the neighbourhood while you are listening to your music and keep the noise down. Your retreat is fully private, we absolutely respect that.

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.

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!

Opera House Views | Harbourfront Cremorne Point
Wake up to stunning Opera House and filtered Harbour Bridge views from this private harbourfront apartment. Perfect for guests who value calm, premium comfort and front-row Sydney Harbour views, it offers an iconic waterfront lifestyle. Positioned directly on the Cremorne Point Foreshore Walk. Steps from the water, a 1-minute stroll to historic MacCallum Pool and just 5 minutes from the ferry—connecting you to Circular Quay and the CBD in 9 minutes.

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!
Popular amenities for Woollahra rentals with a pool
House rentals with a pool

Coastal Zen Oasis with Saltwater Pool & Hot Tub

Cozy 2 bedrooms Grannyflat with air-con & pool

Gladesville By The Water

Gordons Bay Vista

'ISLA' South Coogee

Salty Views on Cross St Bronte

3 Bd home with pool and fireplace heart of Bondi

4 BR, Peaceful, Centrally located family retreat
Apartment 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

Modern apt in Central Sydney: Harbour Views & Pool

Sunny 1 Bedroom City Apartment with Rooftop Pool

Darling Harbour Apart Waterview near ICC and Star

Fantastic Sydney CBD with View
Other holiday rentals with a pool

Self Contained Chic & Cozy Hotel Studio Apartment

Luxury Oceanfront getaway

3BR Family Oasis in Paddington | Pool & Near Bondi

One Darling Waterfront City View

Sydney Harbour View Penthouse

Luxury Apartment Overlooking City and Darling Harbour

Treetops, King Bed, Car Space

Apt city views iconic location with parking
When is the best time to visit Woollahra?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €177 | €147 | €133 | €113 | €104 | €101 | €86 | €110 | €108 | €142 | €136 | €133 |
| 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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- Darling Harbour
- Sydney Opera House
- Manly Beach
- Wollongong Beach
- Avalon Beach
- Bronte Beach
- Terrigal Beach
- Maroubra Beach
- Accor Stadium
- Qudos Bank Arena
- South Cronulla Beach
- Copacabana Beach
- Clovelly Beach
- Dee Why Beach
- Icc Sydney
- Newport Beach
- Sydney Town Hall
- Coledale Beach
- The University of Sydney
- Tamarama Beach
- Mona Vale Beach
- University of New South Wales
- Bulli Beach
- Freshwater Beach





