Family-friendly vacation rentals in Woollahra

4.98 out of 5 average rating, 152 reviews

A spacious living area features large sliding glass doors opening to a deck with water views. Seating includes a hanging chair and various woven chairs around a glass table, complemented by decorative plants on the tabletop.

Home in Bundeena

Bundeena Beachside Oasis

This newly renovated home provides timeless beach house appeal: sweeping water views, indoor/outdoor living and that all-round 'oasis' feel. Special bonus... being able to experience an equally dreamy sunrise and sunset! The property's rare balance of modernity and warmth makes you instantly feel at home. Whether you're soaking up rays on the seaside terrace or seeking a moment of shaded tranquility in the lush, cascading garden - every aspect of this house offers a little bit of magic.

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 103 reviews

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

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!

FamilyIndoor spacesAccuracy

4.96 out of 5 average rating, 128 reviews

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

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

Indoor spacesFamilyWifi

4.86 out of 5 average rating, 196 reviews

A bright living space features a comfortable grey sofa adorned with orange and grey cushions. A wooden dining table with chairs is nearby, accompanied by a small television and a decorative rug. Large windows allow natural light to fill the room.

Condo in Double Bay

Stylish Art Deco apartment

Double Bay is a stylish harbourside enclave on the foreshore of Sydney Harbour. The apartment is located in a charming and very well kept art deco building. Marmle entry, wooden panels all this is part of the typical charm of the building. Our apartment is very well kept and has everything you need for a comfortable stay. As we love to sleep well while we are away from home we invested in a first quality bed, mattress and a very quiet sleeping bed room :)! Love a good bed and quietness!

KitchenIndoor spacesLaundry

4.98 out of 5 average rating, 131 reviews

The living space is illuminated by natural light streaming through large windows. A cozy couch sits beside a wooden coffee table, while a smart TV is mounted on a white console. The bedroom area features a queen size bed, with leafy views visible beyond sheer curtains.

Apartment in Waverley

Designer Coastal Apartment

This designer apartment is newly renovated and positioned on the top floor facing N/E nestled amongst the tree tops with ocean glimpses on the horizon. A quiet and private location with free street parking and only a 10 minute walk to the beach. Enjoy Charing Cross with its boutique shops, cafes, restaurants, pubs and public transport. Bondi junction Westfield and train station is an easy 20 minute walk. Busses are available from nearby streets. *Not suitable for children and infants.

FamilyKitchenQuiet

Apartment in Darling Point

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.

4.96 out of 5 average rating, 183 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.

FamilyIndoor spacesLong stay

Tiny home in Centennial Park

4.86 out of 5 average rating, 135 reviews

Centennial Park Ultra Stylish Close to Beach/City

ULTRA STYLISH Home Free-standing STATE OF THE ART located in quiet safe leafy cul de sac ARCHITECTURALLY UNIQUE North facing Cool, airy, light-filled, separate living + sleeping + Indoor/outdoor space Perfect for FILM peeps: FOX studios, 30 min walk/10 min cycle thru park 1 min WALK- CENTENNIAL/QUEENS PARKS, 8 min drive-Bronte beach, 10 min walk-Bondi Junction/trains 10 min to city On street parking available & free Designed for working, relaxing + attractions

Indoor spacesFamilyDecor

4.84 out of 5 average rating, 155 reviews

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

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!

Indoor spacesKitchenCondition

4.96 out of 5 average rating, 141 reviews

An open-plan living and dining area is illuminated by natural light, featuring a modern couch and a round dining table with four chairs. A sleek kitchen is visible in the background. A private balcony with greenery is accessible through sliding glass doors.

Condo in Paddington

Paddington Parkside

Super quiet, ultra convenient, walk to everywhere location, this apartment provides the ultimate Paddington pad handy to Oxford St shops & restaurants, Centennial Park, historic pubs, the SCG, Allianz Stadium & a 30 min easy walk to the CBD. Tucked away to the rear of the building with a northerly aspect, it is very quiet, private and bathed in natural light. It features modern, recently renovated interiors and is dressed in fresh neutral décor.

FamilyKitchenCondition

Apartment in Darling Point

4.92 out of 5 average rating, 180 reviews

Modern Light-Filled Apartment by Rushcutters Bay

Experience the best of Sydney’s harbourside lifestyle in this beautifully renovated one-bedroom apartment directly opposite Rushcutters Bay. Wake to sparkling water views, enjoy a brand-new designer kitchen, light-filled living spaces and a private balcony - perfect for slow breakfasts or sunset wine. A calm, stylish retreat with cafés, parks and the marina only steps away, offering the ideal blend of relaxation and convenience.

FamilyKitchenCheck-in

4.96 out of 5 average rating, 181 reviews

Large glass doors provide an unobstructed view of the beach, where waves gently lap against the shore. Spacious seating in the living area faces the water, inviting relaxation. Soft curtains frame the scene, and natural light fills the room, enhancing the airy atmosphere.

Home in Bronte

Amazing view beach house footsteps to Bronte Beach

Welcome to Casa Brisa! A unique and spacious beachfront home with uninterrupted views overlooking the iconic Bronte Beach -perfect for holidays and longer stays. Settle into the coastal lifestyle with refreshing ocean dips, scenic coastal walks just steps from your door and easy access to Bronte’s cafés, rockpool and Tamarama Beach. Make this your home by the beach while enjoying space, comfort and oceanfront living.

KitchenFamilyCheck-in

4.94 out of 5 average rating, 179 reviews

A small lounge area features a black two-seater sofa adorned with patterned cushions and a bright red armchair. A floor lamp stands beside the chair, providing additional lighting. Light brown wooden flooring complements the neutral wall colors and contemporary artwork above the sofa.

Apartment in Paddington

Spacious 1 Bedroom apartment

Central fully furnished 1 bedroom apartment (ground floor), fully equipped kitchen and own courtyard in a terrace house. We live upstairs. Private secure entrance. Check in 2pm -6pm! Located in the prestigious Queen St. 20 minutes from the CBD and 20 minutes from Bondi Beach. Great buses. 1-2 people. No children (0-12). Wifi Smart TV Please read The Space and Guest Access.

KitchenIndoor spacesLayout

Popular amenities for Woollahra family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 322 reviews

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

Sydney Darling Harbour Sydney Views

Indoor spacesFamilyTV

4.89 out of 5 average rating, 302 reviews

A modern kitchen area features a dark stone countertop, with a kettle and decorative plant positioned near a large glass window. Beyond the window, a private pool is visible, surrounded by wooden decking and tropical trees, creating a serene outdoor space.

Tiny home in Seaforth

Spa Serenity Cottage with Private Pool & Spa

FamilyKitchenGrill

4.96 out of 5 average rating, 371 reviews

A panoramic view displays the Sydney Harbour, featuring the iconic Sydney Opera House and Sydney Harbour Bridge. The landscape includes a mix of historic and modern buildings, with the water reflecting sunlight. The vibrant atmosphere is enhanced by boats navigating the harbour.

Apartment in The Rocks

World Class location+Pool, Spa+Harbour Bridge View

Indoor spacesFamilyHot tub

Place to stay in Bundeena

A deck area is shown, featuring stylish outdoor seating and a spa. Vibrant flowering plants add color and texture, while views of the water are visible in the background. The scene is bright and inviting, framed by lush greenery.

4.83 out of 5 average rating, 886 reviews

Bundeena Treehouse with Outdoor Spa and Views

FamilyIndoor spacesAccess

4.81 out of 5 average rating, 467 reviews

A panoramic view of the Sydney skyline is showcased, with tall modern buildings and the iconic Sydney Tower visible. Lush green trees in Hyde Park provide a vibrant contrast to the urban landscape, creating a harmonious connection between nature and city life.

Apartment in Surry Hills

Stunning View, Modern, Heart of City

KitchenIndoor spacesCleanliness

4.97 out of 5 average rating, 102 reviews

An outdoor garden space is illuminated by soft lighting, featuring lush tropical plants and a comfortable seating area. The backyard flows seamlessly into the interior, showcasing an inviting living space visible through large glass doors.

Home in Manly

Ultimate Luxury Just 100 Steps from Manly Beach

FamilyIndoor spacesCheckout

4.92 out of 5 average rating, 99 reviews

A spacious outdoor area presents a shimmering pool surrounded by tiled decking. The pristine white exterior of the villa contrasts with the blue water. Large windows and decorative arches are visible, contributing to the elegant architectural style. Lush palm trees provide a tropical feel.

Villa in East Killara

Killara Luxurious 8BR House 360 degree view

Indoor spacesKitchenHot tub

5 out of 5 average rating, 186 reviews

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

Supreme Sydney Rocks Suite + Spectacular Pool View

FamilyKitchenHospitality

Family- and pet-friendly home rentals

Apartment in Bondi Junction

An ornate heritage facade showcases intricate golden architectural details and sculptures beneath a clear blue sky. The building features numerous arched windows, creating a striking contrast with the modern structures surrounding it.

4.82 out of 5 average rating, 149 reviews

Neighbourhood By TWT- The Vegemite Heritage Studio

Indoor spacesFamilyDecor

Guest suite in Freshwater

An outdoor terrace is visible, featuring a wooden table set for dining alongside comfortable seating and a plush daybed. A large BBQ grill is positioned nearby, and expansive glass doors provide a view into the light-filled interior of the studio.

4.95 out of 5 average rating, 201 reviews

Studio cottage close to the beach

Indoor spacesFamilyParking

4.92 out of 5 average rating, 105 reviews

A compact kitchen area features modern appliances, including a dishwasher and coffee maker. A light-colored breakfast bar with two wooden stools provides seating. A tall bookshelf filled with various books stands nearby, and a movie poster is displayed on the wall.

Apartment in Bondi Beach

Bondi mid-century modern snug

Indoor spacesKitchenBeach

4.99 out of 5 average rating, 218 reviews

Apartment in Coogee

Coogee's Best Views Absolute Beachfront

FamilyIndoor spacesSleep quality

4.89 out of 5 average rating, 151 reviews

Apartment in Bondi Beach

Breathtaking Bondi VIEWS

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 185 reviews

A spacious living area is showcased, featuring a comfortable sofa and a round ottoman. Large floor-to-ceiling windows provide stunning ocean views, while natural light fills the room. A neutral color palette with light wood flooring enhances the airy atmosphere, inviting relaxation.

Home in Tamarama

Absolute Tamarama Beachfront on Bondi Coastal Walk

KitchenIndoor spacesShared spaces

Vacation home in Bondi Beach

A living area features a spacious gray sofa, accented with orange cushions. A round coffee table sits in front, while floor-to-ceiling bifold glass doors provide direct views of Bondi Beach. Two outdoor chairs are positioned on the balcony, inviting relaxation.

4.87 out of 5 average rating, 126 reviews

Bondi Heaven Beachfront Apartment

Indoor spacesFamilyHospitality

Apartment in Darlinghurst

4.99 out of 5 average rating, 339 reviews

Sydney City Penthouse, vast City & Harbor Views

KitchenFamilyHiking

Family-friendly home rentals with a pool

A well-appointed bedroom features a spacious bed with soft linens and an array of decorative pillows. A textured throw is draped across the bed. An oval mirror reflects natural light, while a window showcases a glimpse of the Sydney Harbour Bridge.

4.91 out of 5 average rating, 106 reviews

Harbourview Sydney | Pool + Opera Views

KitchenIndoor spacesGetting around

Apartment in Elizabeth Bay

4.82 out of 5 average rating, 212 reviews

Stylish Harbourside Apartment in Elizabeth Bay

KitchenIndoor spacesTV

Apartment in Darlinghurst

A view of the harbour showcases various boats anchored in the water, framed by lush greenery and contemporary buildings. Tall residential structures rise in the background under a clear blue sky, contributing to the vibrant coastal atmosphere.

4.94 out of 5 average rating, 465 reviews

Resort Style Apt with View & Car Space

FamilyIndoor spacesTV

A modern living space showcases a well-furnished area with a comfortable lounge chair, small side table, and a textured rug beneath. A stylish kitchen is visible in the background, illuminated by soft lighting. Green plants add a fresh touch near the window, enhancing the vibrant atmosphere.

4.99 out of 5 average rating, 162 reviews

Stunning One Bedroom Art Deco Apartment

KitchenFamilyCheck-in

4.77 out of 5 average rating, 110 reviews

An open-plan living and dining area is showcased with a soft-colored sofa adorned with cushions and a round dining table featuring white metal chairs. Light wood flooring is complemented by a neutral area rug, and wall art reflects a coastal theme.

Apartment in North Bondi

Relaxed coastal living in Bondi beach pad

KitchenFamilyView

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.

4.79 out of 5 average rating, 210 reviews

Light Filled Studio On Trendy & Vibrant Macleay St

KitchenIndoor spacesLaundry

4.89 out of 5 average rating, 285 reviews

The exterior of a modern guest house is displayed, featuring a spacious lawn with neatly trimmed grass. A covered seating area with outdoor cushions is visible, along with tropical plants placed around. Large glass doors lead into the interior, blending nature with design.

Tiny home in Malabar

Beach side private house with pool access

Indoor spacesKitchenDecor

The living area features large windows offering views of the Sydney skyline and the Harbour Bridge. A comfortable seating arrangement includes a sofa, a television, and a minimalist dining table with chairs. Natural light fills the space, enhanced by neutral decor and a plush rug.