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Family-friendly holiday rentals in Annandale

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Annandale

  • Total holiday rentals

    Explore 40 holiday rentals in Annandale

  • Nightly prices starting at

    Annandale holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 1,020 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Annandale holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Annandale rentals

  • 4.8 Average rating

    Annandale stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Annandale

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
The garden chalet is surrounded by lush greenery, with a wooden facade and multiple glass doors. Natural light fills the interior space, while vibrant plants enhance the inviting outdoor atmosphere.
Guest house in Glebe
4.92 out of 5 average rating, 399 reviews

Leafy garden chalet in InnerWest with water views

Charming self-contained garden chalet in Inner Sydney in small leafy backyard off Blackwattle Bay. Access through house. Cook St is off Glebe Pt Rd with its cafes, pubs, bookshops, amenities, and Broadway Shopping Centre. 10 min walk thru park to TramSheds. Ferry to Barangaroo at bottom of road. Buses, lightrail to fish markets, Darling Harbour, markets, Central. Universities close. Friendly neighbours, parrots, possums, kookaburras. Happy dog, owner onsite. Will sleep 3 but 2 most comfortable.

Guest favourite
Guest house in Leichhardt
4.85 out of 5 average rating, 102 reviews

Boutique Garden Cottage Sydney

Tucked away in a beautiful leafy setting in the heart of Leichhardt, Mr Muddy Lion is a charming private boutique cottage — a self-contained retreat with a pool, in one of Sydney's most loved neighbourhoods. The cottage offers a comfortable queen bedroom, a cosy lounge with Netflix, a fully equipped kitchenette, and your own bathroom with laundry. A queen air bed is available for extra guests. Step outside to enjoy the pool and BBQ area — a lovely spot to relax and soak up the Sydney sunshine.

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, 191 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!

Guest favourite
A cozy sleeping area features a spacious bed with a green bedspread and decorative pillows. A small dining table with two chairs is positioned nearby. Natural light floods the room through a large window, while a fan provides additional comfort.
Tiny home in Annandale
4.9 out of 5 average rating, 114 reviews

Serenity Studio, Granny flat

Serenity studio is a tranquil place with an independent entrance, perfect for solo travellers or couples looking for a quiet stay in the inner west, close to the city. Wake up in air conditioned comfort in a cozy queen bed to views of the park and the sounds of birds chirping. Spot the kookaburra if you can. The kitchenette is equipped with a coffee machine, toaster, microwave and mini fridge. Perfect for breakfast and light meals. We’re always happy to share tips on food and things to do!

Top guest favourite
Flat in St Leonards
4.97 out of 5 average rating, 128 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.

Top guest favourite
A cozy living area features a gray sofa paired with two tan leather chairs, enhancing the relaxed atmosphere. A round black coffee table with a textured surface is centered on a light area rug. Warm light is provided by a ceiling fixture, illuminating the art decor.
Home in Annandale
4.96 out of 5 average rating, 111 reviews

Contemporary Victorian Charm

Kick back and relax in this calm, stylish space. This charming Victorian two bedroom single level terraced house is located close to the city in the historical village of Annandale. This cute as a button home sits near the Tramshed's chic eateries, tramline, bus which whisks you into the city. This home possesses light contemporary interiors complimented by a deep, shaded rear garden, alfresco terrace and auto door off-street parking within a tranquil location in a broad, tree-lined avenue.


Top guest favourite
A modern building exterior is shown, characterized by a striking black facade and a large garage door. Large windows allow natural light, while an overhanging roofline provides architectural interest. Lush greenery and trees are visible in the background, adding to the overall appeal.
Flat in Leichhardt
4.93 out of 5 average rating, 129 reviews

Cosy studio

Street parking only Convenient location and close to the city. Brand new studio, clean and comfortable. 10mins walk to shopping centre 10 mins walk to the bay run, 5 mins walk to restaurants, shops, tennis and basketball courts. -5.5km from Sydney CBD (10-12mins Drive) -2min walk to Hawthorn Light Rail -15mins via Light Rail to Fish Market -20mins via Light Rail to Darling Harbour -25mins via Light Rail to Chinatown -25mins via Bus Route 437 to Sydney CBD Property ID: PID-STRA-81128

Top guest favourite
An aerial view captures the scenic blend of waterways and urban skyline, showcasing the Sydney Harbour and tall city buildings. Lush greenery lines the shore, contrasting with the bustling harbor and intricate bridge structures, highlighting both natural beauty and city life.
Flat in Glebe
4.93 out of 5 average rating, 151 reviews

BEAUMELSYN - an Oasis in Glebe

BEAUMELSYN - Large Victorian Terrace in eclectic Glebe - self contained 1 bedroom basement garden APARTMENT. A extra bedroom available @ fee . Glebe oldest suburb in Sydney - professionals, students, mainstream & bohemian. Minutes to the CBD, Harbour , foreshore parks, Opera House, Sydney University. 5 min Walk to VILLAGE ,cafes, bars, shops , restaurants , supermarket , pubs, more than 10 restaurants, bikes, buses, Light Rail, ferry. Quiet leafy Harbourside neighbourhood.

Top guest favourite
A charming courtyard is framed by vibrant green plants and flowering shrubs. A light-colored door serves as an entry point, with a small seating area visible to the side. The stone pathway leads to a textured surface, enhancing the outdoor tranquility.
Guest house in Annandale
4.96 out of 5 average rating, 408 reviews

Annandale Self Contained flat & area 'Old Stable"

A self-contained separate flat with its own relaxed Courtyard. Combined Kitchenet for light eating ,incl, toaster,microwave, kettle,Coffee Pod Machine, Bathroom & Laundry.(Dryer, W/Mach,iron& Board)Hair dryer and straightener Air Conditioned and courtyard. Close to SYD/CBD. Ideal for Sydney City Festivals, MWS/ Long w/e ,close to city bus stops. Annandale Village 300 m away. Buses & Lightrail very close. Close to RPA Hospital. Ideal for a comfortable stay if renovating in the area.

Guest favourite
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
4.84 out of 5 average rating, 154 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
The entrance of the terrace home is framed by decorative ironwork. A warm interior glow is visible through the open door, leading into the living space. The house number is clearly displayed as '37,' and a picket fence provides a welcoming boundary.
Home in Newtown
4.84 out of 5 average rating, 166 reviews

Stylish Aircon Terrace Near Newtown, Train to City

Peaceful 2 bedroom terrace for 4 people. Only 8 min walk to popular Newtown shopping and train. Only 5 min train ride to Sydney Harbour Featuring: * 2 full bedrooms with queen beds * fully equipped kitchen * internal washer * beautiful, sunny garden with atrium * separate living and dining space * smart TV with Netflix etc. * WiFi * 5-10 min walk to Newtown centre * close to public transport/train station * Quiet narrow st with 24hr parking.

Top guest favourite
A spacious living area features large glass doors that open to a private garden. Natural light floods the space, illuminating a neutral sofa and a striped area rug. Soft greenery and stone pathways are visible outside, creating a serene outdoor environment.
Guest house in Mosman
4.99 out of 5 average rating, 177 reviews

Balmoral Slopes Guesthouse

This beautiful new airconditioned guesthouse designed by renowned Sydney architect Luigi Rosselli is a detached separate dwelling located near our private home. Ideal for couples and families with babies and small children. - Bus stop 50m from doorstep - will take you into Mosman village and the CBD. - 400m walk to Balmoral Beach cafes & restaurants. - Street parking available close to the guesthouse. Secure access via security gate.

Popular amenities for Annandale family-friendly rentals