Family-friendly vacation rentals in Robertson

Shelter at Gerroa

Feel the instant relaxation while taking in sweeping coastal views from this stylish living space, just 90 mins south of Sydney and a 700m walk to Seven Mile Beach. Open the bifolds to feel the ocean breeze and extend the space out to an expansive deck. Or get cosy by the fireplace in colder months. With breakfast servery and outdoor lounge area, you’ll be spoilt for places to gather. Your pootch can run wild in the grassy, fully fenced yard, and enjoy time at the region’s dog friendly beaches.

Wollemi House - in forest and waterways with pool

Escape to your private oasis nestled among beautiful trees and surrounded by breathtaking natural scenery in the Southern Highlands of Robertson. This gorgeous property sits on a sprawling acre of land with a rare Wollemi pine tree in the backyard and a serene creek that winds through the property. With its pool and deck, this tranquil retreat is the perfect place to kick back and relax on warmer days. And when the nights turn chilly, cozy up by the fire pit and gaze up at the stars above.

Cloud Pad – Mountain Retreat at CloudFarm

Welcome to Cloudfarm Cloudfarm is a unique 33-acre sanctuary perched at the highest point of the Illawarra escarpment, offering breathtaking, ever-changing views — where the sky feels close enough to touch. A world away, yet just 7 minutes from Robertson and 25 minutes from Bowral and Moss Vale, it’s the perfect base for a romantic escape or a slow meander through the Southern Highlands — with its cool-climate vineyards, farm gate produce, misty trails, and a touch of chic country charm.

Luxurious,Cosy & Relaxed Apartment with Spa Access

Are you looking for something a little bit special? Located in picturesque Robertson, an easy 20 minute drive from Bowral, ‘Highlands Meadow View’ is a modern spacious light filled 2 bedroom apartment offering guests a luxurious and quiet getaway in a pretty, rural setting. Situated just 2 minutes by car from the main street of Robertson, it is an ideal base if you’re travelling down for a wedding, exploring the Highlands or visiting Kiama and other beautiful parts of the South Coast.

Rosewood Cottage - on a working regenerative farm

Renovated 2 bedroom 1930s Cottage, perched on the gentle slopes of a lush 120 acre working regenerative farm, where happy sheep and cows graze on chemical-free pasture. Relaxing, family-friendly, off-grid, with breathtaking views of the beautiful Kangaroo Valley escarpment. Only 4kms from the charming Kangaroo Valley Village and 20min from historic Berry and its nearby beaches. Rosewood Cottage will offer you a comfortable and cosy stay with everything you need for a short getaway.

Pear Tree Cottage

Enjoy a peaceful country retreat in the heart of the Highlands surrounded by nature at its best. This spacious, newly renovated, two-bedroom cottage is a separate dwelling situated on 5 acres of parkland that can sleep up to 5 people. It has a kitchenette, dining table and comfy lounge with a cosy warm fireplace for cold nights and is just a 5 minute drive or 30 minute walk to Bundanoon village. Pear Tree Cottage gets its name from the ornamental pear trees that line the driveway.

WATERSHED - Robertson

Welcoming country chic interiors with all the mod cons. You will enjoy luxury finishes in this converted machinery shed. Fully insulated, with double glazed windows & doors. There is a wood fire & heaters. The shed is 80+ metres away from the 1880s farmhouse where we live & so you are far enough way to feel that you have the property to yourselves. There are dogs, alpacas, sheep. A wonderful farm stay property, a walk away into Robertson or a very short drive. @watershedrobertson

100 acre lush mountain paradise all to yourself

Ameroo Farm is the ideal mountain hideaway, perfectly placed 10km from the vibrant township of Berry and the quaint village of Kangaroo Valley. Surrounded by nature with beautiful mountain views and lush green paddocks, Ameroo is a working family farm, with an abundance of wildlife including wombats, kangaroos, wallabies and echidnas. Collect fresh eggs from the chickens, hand feed Patchy the miniature horse and Quinny the cow. Wander the open spaces and enjoy the quiet life.

Contemporary Rural Luxury in Lush Garden

Nestled on the edge of beautiful Bowral, this contemporary two-bedroom space is your idyllic escape. Enjoy modern amenities, including an EV charger, in our stylish and sunny self-contained Guest Wing. Your backyard? Step out onto stunning walking trails in Mansfield Reserve and immerse yourself in nature's serenity. And you're just a 10-minute drive from Bowral's vibrant cafes and shops. This property offers the perfect blend of rural tranquillity and urban convenience.

The Shed at Penrose

Cosy self Contained Apartment on a small 5 acre working horse training property based in Penrose, Southern Highlands NSW Our apartment can accomodate a couple or a family of 4 making it an easy choice for somewhere to stay whilst visiting the beautiful Southern Highlands. Be greeted in the morning by our small family of horses or bring your own horses for a riding holiday, where an accredited coach is also available for lessons and the Penrose forest is on our doorstep.

Japanese Studio Fitzroy Falls

Relax in our private beautiful Japanese Studio , open plan bedroom and living room with seperate small bathroom. NOT suitable for children or pets. The Studio has a bar fridge , microwave, toaster, coffee pod machine and kettle. No kitchen. .Enjoy stunning 9 acres of gardens . Perfect location for photo shoots, wedding & ceremonies We also have 'The Dairy' which is a 1 bedroom (1 queen bed) cottage with a kitchen and fireplace. Strictly Non smoking. STRA 6648

The Escarpment Loft / pet friendly

Nestled on an escarpment overlooking the Great Dividing Range, at the top of Macquarie Pass and set amid 14 acres of lush countryside, this two-bedroom contemporary apartment is an ideal rural escape. Whether you're passing through for a night or you’re taking a few days to recharge, you will feel the cares of the world fade away as you drive through the gates and make your way up the winding road to the residence.