Holiday rentals in Observatory Hill

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Top-rated holiday rentals in Observatory Hill

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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.
Apartment in Mosman
4.98 out of 5 average rating, 190 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 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.
Flat in The Rocks
5 out of 5 average rating, 174 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.

Top guest favourite
Flat in St Leonards
4.97 out of 5 average rating, 118 reviews

Luxury Designer Penthouse 1BR•Skyline View•Parking

This penthouse offers excellent privacy and tranquility, making it safe to leave the curtains open at night. You won't find the city lights too bright to sleep, but instead, you'll enjoy the charming urban scenery, reminiscent of scenes from a TV drama. Stream piano music via Bluetooth, light up some aromatic candles, pour yourself a glass of wine, and unwind while admiring the endless city lights and starry night sky. You'll feel relaxed and forget all your worries in this serene atmosphere.

Superhost
A spacious living room is featured, showcasing a large sectional sofa adorned with decorative cushions. Natural light streams through a window with plantation shutters, illuminating the polished wooden floors. A small plant sits on a side table, complemented by a decorative basket on the floor.
Home in Millers Point
4.81 out of 5 average rating, 288 reviews

The Rocksberry - Charming Terrace in the Rocks

The Rocksberry is an elegant heritage two-storey terrace, which has been newly renovated and refurbished. Our house is situated in The Rocks, on one of the oldest streets of Sydney, with Observatory Hill in our backyard and Barangaroo at our doorstep. Perfect for overseas travellers who wish to explore Sydney and its historical sites, or locals looking for a relaxing getaway. Please note - We do not allow parties. Quiet hours from 9pm to 8am (We are situated in Sydney CBD's residential area).

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.
Flat in Vaucluse
4.97 out of 5 average rating, 124 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 favourite
A serene view is presented from the window, showcasing the calm waters of Cabbage Tree Bay. The Fairy Bower ocean pool is visible alongside rocky outcrops and the lush greenery of the surrounding coastline.
Flat in Manly
4.98 out of 5 average rating, 122 reviews

Luxury Manly Oceanfront Getaway

Be mesmerised by endless ocean views across to iconic Manly Beach and beyond from this newly renovated top floor apartment. Perfectly positioned on the oceanfront walk between Manly and Shelly Beach, there are plenty of cafes and outdoor activities within an easy scenic stroll. Enjoy the sights and sounds of what the Northern Beaches has to offer from the luxury of your own piece of paradise. Sydney Harbour ferries within walking distance and world class swimming/snorkeling on your doorstep.

Guest favourite
Home in Millers Point
4.88 out of 5 average rating, 128 reviews

Exclusive living in a Historic Home

With 180 degree views of Barangaroo and Balmain and a courtyard for enjoying afternoon drinks, this 3 storey home is fitted with all the modcons including smart TV, WIFI, luxury Egyptian cotton linen, air con, washer/dryer, marble kitchen, wooden floors, rain shower heads, customised wardrobes, a clawfoot bathtub and Victorian fireplaces. 5 min walk to Barangaroo, 10 mins to Circular Quay and CBD and around the corner from some of the best restaurants and bars that Sydney has to offer.

Guest favourite
An aerial view captures the Woolloomooloo Wharf, showcasing its modern architecture along the waterfront. Marinas with boats are visible, while lush greenery outlines the distant skyline of Sydney, featuring landmarks like the Harbour Bridge and Opera House under a clear blue sky.
Flat in Woolloomooloo
4.93 out of 5 average rating, 149 reviews

Unique studio at Historic Wharf

Stunning studio apartment in the renowned Woolloomooloo Wharf built in 1915. Its beautiful views over the water and Potts Point are key, but this studio has everything you need for a city visit or a staycation. Conveniently placed just minutes to Potts Point and within walking distance to all of Sydney's main attractions: Botanic Gardens, Opera House, Harbour Bridge, Art Gallery NSW, Museum of Contemporary Art and the CBD. No parking Early check in or late check out (if available): $50

Guest favourite
A spacious living area features large windows that provide ample natural light and panoramic views of the city. A comfortable green sofa is positioned beside a round coffee table, with decorative cushions adding texture. A dining table sits nearby, complemented by a potted plant.
Flat in The Rocks
4.95 out of 5 average rating, 128 reviews

Worldclass location w/ pool, sauna & gym

Experience the magic of Sydney from our stunning apartment in The Rocks. Wake up to panoramic views of iconic landmarks like the Opera House and Harbour Bridge. Walk to George Street or Barangaroo for the best bars and restaurants. Enjoy easy access to ferries for trips to Manly, Watsons Bay, or Taronga Zoo. Indulge in sophistication and vibrant city life, with world-class amenities and historical charm. Perfect for the Vivid Sydney festival. Book now for an unforgettable stay!

Top guest favourite
Guest house in Saint Ives
4.99 out of 5 average rating, 142 reviews

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.

Guest favourite
Home in Seaforth
4.84 out of 5 average rating, 153 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!

Guest favourite
Flat in Millers Point
4.9 out of 5 average rating, 173 reviews

Luxury Heritage- next to Harbour and Barangaroo!

Welcome to your perfect Sydney getaway! Nestled in the heart of Sydney's historic The Rocks and just a short walk from Barangaroo and the CBD, this brand new, elegant heritage apartment offers the ideal blend of contemporary luxury and charming heritage character. Whether you're visiting for business or leisure, this spacious and beautifully furnished apartment provides all the comforts of home—without the high price tag of a hotel.

Popular amenities for Observatory Hill holiday rentals