Holiday houses in Woollahra Municipal Council

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Top-rated holiday rentals in Woollahra Municipal Council

Guests agree: these stays 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, 192 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 favourite
An outdoor terrace features a heated infinity pool reflecting the city skyline and Sydney Harbour. Lush greenery and palm trees surround the area, providing a tranquil view over Rushcutters Bay Park, with the iconic Harbour Bridge visible in the distance.
Apartment in Darling Point
4.97 out of 5 average rating, 29 reviews

OMG Sub-Penthouse + Pool + Bridge Views

This unique sub-penthouse boasts uninterrupted views of the Harbour Bridge and city skyline. Overlooking Rushcutters Bay and its world-class marina, the home features access to Yarranabe Park and offers luxury living in a prestigious harbour front location. Split over two levels in a block of only two homes, it provides privacy and tranquility while remaining convenient to Double Bay, the CBD, and local beaches. With trains, buses, and ferries nearby, it is an ideal base for enjoying the city.

Top Guest favourite
The open living area features a small dining table surrounded by wooden chairs, complemented by a spacious blue sofa. A vibrant wall artwork adds a pop of color, while the adjacent kitchen with sleek furnishings can be seen in the background.
Home in Paddington
4.96 out of 5 average rating, 101 reviews

Little Edie charming architect designed cottage

A gorgeous, free-standing two level stables converted into a chic, fully self contained cottage in the heart of Paddington's leafy streets, Little Edie is an architecturally designed jewel box for grown ups providing the perfect place to rest and relax during your next visit to Sydney. Centrally located, it is two blocks from Oxford Street's boutiques, bars, restaurants, public transport and just a few minutes from the city, sports stadiums and glorious beaches. We love giving local tips too!

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, 127 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

Guest favourite
A lounge area features a brown leather sofa paired with a round, light-colored coffee table. Black-and-white framed photographs adorn the wall. A large television sits atop the mantel above a decorative fireplace. A view of the kitchen area can be seen in the background.
Home in Woolloomooloo
4.92 out of 5 average rating, 315 reviews

Harbour Terrace 2BR Central Woolloomooloo

- Harbour side location, easy stroll to cafes and bars ✅ - Free to use full sized tennis and basketball court 1 minute walk with 4 X tennis racquets and Basketball supplied ✅ - Playground for the kids ✅ - Award winning matress' with fresh high quality linen ✅ - Full kitchen with all essentials, coffee, tea etc ✅ - Each bedroom has 32" Smart TV with Netflix ✅ - Washer/Dryer combo with liquid supplied ✅ - Fresh Towels ✅ - Beautiful walkable location close to Opera house and botanic gardens ✅

Top Guest favourite
A light-filled living area is furnished with a spacious white sectional sofa. A natural fiber rug complements the timber flooring. An open kitchen island with marble detailing is visible, while glass doors provide access to the outdoor deck and views of the surrounding greenery.
Apartment in Darling Point
4.96 out of 5 average rating, 181 reviews

Luxury Apartment - Harbour and City Skyline Views

Elanora - A Gracious Apartment A historic building but completely reconfigured and renovated. One of only 4 apartments in the building. 130 m² / 1400ft² A large, open timber deck looks out over Rushcutters Bay and through yachts and out to the northern end of theHarbour Bridge. Two generous bedrooms and bathrooms and an open plan living, dining and kitchen space. We are close to beautiful Rushcutters Bay Park and the CYCA. Timber floors throughout, aircondtioning, Foxtel and Netflix.

Top Guest favourite
A sandy beach area is lined with trees and homes, where individuals enjoy the water and sun. The shoreline curves gently, leading to clearer waters that reveal rocky formations. In the distance, the outline of a city skyline is visible against a bright blue sky.
Guest suite in Watsons Bay
4.98 out of 5 average rating, 273 reviews

Camp Cove Tropical Retreat at Watsons Bay

A spacious contemporary apartment with a large under cover verandah, and private tropical garden. The living area is filled with natural light and looks out to a beautiful and tranquil palm-filled garden. We are located 100m from beautiful Camp Cove Beach and just a 5 minute walk to the Watsons Bay ferry service accessing harbour suburbs and the CBD - just 20 minutes away. If you are attending a wedding or getting married we are a short stroll to all of Watsons Bay's wedding venues.

Top Guest favourite
Apartment in Watsons Bay
4.97 out of 5 average rating, 30 reviews

Roberts at Watsons Bay - Watsons Bay 2030

Escape to a peaceful retreat in the heart of Watsons Bay, NSW - ideal for those seeking tranquility, nature, and a slower pace of life. Tucked away off the main street and surrounded by lush greenery, this private apartment offers a serene, hidden escape while still being moments from everything Watsons Bay has to offer. Just a 4-minute stroll brings you to the iconic Watsons Bay Hotel and the wharf, where you can enjoy waterfront dining, harbour views, or hop on a ferry into Sydney.

Guest favourite
A modern living area features a gray sofa adorned with decorative pillows and a vibrant yellow throw. Natural light pours in through two windows framed by exposed sandstone walls, showcasing the lush greenery outside. A glass coffee table rests on a soft carpet, complementing the space.
Guest suite in Cremorne Point
4.89 out of 5 average rating, 390 reviews

Lavish Suite with Stone Archway Patio

Private and elevated from the street, entry to the apartment is framed by a beautiful sandstone arch. The interior spaces are surrounded by established lawns and gardens that are for the exclusive use of the guest. Cremorne Point is located on the shores of Sydney Harbour. Surrounded by beautiful harbourside walks with a views of Sydney Harbour Bridge and the Opera House. Minutes walk from the property you will discover gorgeous grassy slopes ideal for a sunset champagne picnic.

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 Elizabeth Bay
4.79 out of 5 average rating, 210 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.

Top Guest favourite
A lush garden area features vibrant green grass that gently slopes down towards the tranquil waters of Sydney Harbour. A large tree stands prominently, offering shade. Various boats are anchored in the calm bay, surrounded by the greenery of the shoreline.
Apartment in Kurraba Point
4.98 out of 5 average rating, 109 reviews

Harbour View Shellcove

Unique Waterfront Retreat with Water Access. Welcome to your dream Sydney escape! Nestled in the highly sought-after neighbourhood of Kurraba Point, our charming 2-bedroom apartment offers you the perfect blend of tranquillity and urban convenience. Here, you'll enjoy breathtaking harbour views, direct access to a private jetty, and swift access to the city via a 9-minute ferry. Book your memorable stay today.

Guest favourite
Home in Double Bay
4.92 out of 5 average rating, 39 reviews

Serene Double Bay Home w/ Private Garden Courtyard

A warm and inviting Double Bay retreat featuring light-filled interiors, two serene bedrooms, a modern bathroom with a bathtub, a spacious living area, and a fully equipped kitchen. Enjoy the peaceful garden and a small patio with a table and chairs, perfect for morning coffee. Just a short walk to the beautiful Double Bay foreshore, this home offers a calm and relaxing stay for up to six guests.

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