
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 $34 NZD 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, 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.
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

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.

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.

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!

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!

Prime location 180° Sydney Views
This apartment is located in Sydney's Paris end of Potts Point. It is private, sun-filled, North-West aspect, views to Woolloomooloo Bay, Sydney skyline, Opera House and Harbour Bridge. It is an easy walk to Kings Cross Station, The Royal Botanical Gardens, Sydney CBD, and Potts Point's vibrant night life and restaurants. The building has lush garden surroundings and a rooftop sundeck with a 360° Harbour View pool.
Popular amenities for Woollahra rentals with a pool
House rentals with a pool

Fairlight House

Gladesville By The Water

Cozy 2 bedrooms Grannyflat with air-con & pool

Bundeena Base Art House Sea View Solar Heated Pool

3 Bd home with pool and fireplace heart of Bondi

Stunning 3 br home near beach with pool and sauna

Stylish, spacious comfort. Ideal location.

Salty Views on Cross St Bronte
Condo rentals with a pool

Spacious apartment with huge undercover balcony

Darling Harbour Apart Waterview near ICC and Star

Lovely One Bedroom + Study with Infinity Pool

Darling Harbour Breeze with car park

Rosebery 2BR| Free Parking | 8 min to Woolworths

1BR + Parking | Close to Airport | Train & CBD

Fantastic Sydney CBD with View

Quiet Living•Family Friendly•Netflix•Free Parking
Other holiday rentals with a pool

Opera House Views | Harbourfront Cremorne Point

Bondi Breeze apartment

Stunning Unit City Harbour Views + Parking +BBQ

Supreme Sydney Rocks Suite + Spectacular Pool View

OMG Sub-Penthouse + Pool + Bridge Views

Darling Point Rd | Elegant Apartment

3BR Family Oasis in Paddington | Pool & Near Bondi

2 Bedroom Coastal Oasis with Heated Pool and Spa
When is the best time to visit Woollahra?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $350 NZD | $290 NZD | $262 NZD | $222 NZD | $205 NZD | $200 NZD | $169 NZD | $217 NZD | $214 NZD | $281 NZD | $269 NZD | $262 NZD |
| 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
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- Bronte Beach
- Terrigal Beach
- Accor Stadium
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- Qudos Bank Arena
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- The University of Sydney
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- University of New South Wales
- Tamarama Beach
- Mona Vale Beach
- Freshwater Beach
- Taronga Zoo Sydney





