Private suite holiday rentals in Southern Highlands

Bradman Studio -tranquil garden, easy walk to town

Host of the Year Finalist 2025! Located in the charming Old Bowral precinct, Bradman Studio is a level, easy 10 min walk to Bowral's main street and only 100m from picturesque Bradman Cricket Oval. Spacious open layout, abundant natural light and wide views over our mature, very private rear garden. Adjoining deck for outdoor dining. A/C and double glazed windows assure comfort year round. KS bed, heated bathroom floor, beautiful quality bedlinen & well equipped kitchenette. On-site EV charger.

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.

Kialla Down, rural vista, peace and quiet

Lovely views across to Mt Gibraltar, attracting 5* feedback from 95% of guests. Sunny aspect. Quiet, semi-rural neighbourhood. Small patio with garden furniture and barbecue. Free car parking adjacent to private ramped entrance. Key-safe access. By negotiation a small, mature, well-behaved dog accepted in living area, (not in bedrooms, please) and under control in garden area. My place is unsuitable for long term rental so I am not depriving anyone of an affordable housing opportunity.

Haven Bundanoon Southern Highlands

Your perfect base to explore beautiful Bundanoon and the Southern Highlands. Completely private, located at one end of our home is “Haven”, your very own guest suite. You'll enjoy having your own access, stylish decor and little extras! Comprising of one or two bedrooms (please confirm one or two rooms at booking) and spacious ensuite bathroom: perfect for the solo traveller, couples, or friends. Comfortable queen size beds, small sitting area with garden views, spacious shower, and spa bath.

Little Ronnie's Cottage

Recently refurbished (2021) cottage set in our lovely tiered private garden on the slope of Mt Alexander. Views to the Mittagong Ranges and a very quiet and peaceful location. Easy 15 min walk to train station and many food and drink venues. A/C (heat/cool), wood burner, ceiling fan, double glazed windows. Queen bed, bathroom with heated floor, heated towel rail and a well equipped kitchenette with basic breakfast provisions including tea and coffee. Private, peaceful & perfect for couples.

29 on Shepherd

29 On Shepherd is a small original 1940’s , cosy cottage within easy walking distance to the centre of Bowral. The owner lives in the back 2 storey extension connected by a solid door with total privacy for both and is often away. Noise is not an issue! The two guest bedrooms have one king and 2 king single very comfortable beds, reverse cycle air conditioning, overhead fans, and wardrobe space. A full bathroom with bath, shower and toilet + powder room. Kitchenette, eating area and lounge.

The Studio @ The Vale Penrose

A secluded garden retreat with private rainforest spa Set within five acres of beautifully manicured gardens in the quiet village of Penrose, The Studio @ The Vale Penrose is an intimate and refined escape designed for couples seeking peace, privacy, and a touch of indulgence. Part of The Vale Penrose—an established luxury farm stay welcoming guests since 2019—the Studio offers a more secluded, nature-immersed experience, where thoughtful comforts meet the beauty of the Southern Highlands.

The Captain’s Cabin

Nestled in our citrus and nut orchard is the 'Captain's Cabin'. A hideaway in your own private section of the garden, with an amazing outdoor bath, ample cooking facilities inside and out, and fire pit, not to mention a comfortable queen bed with natural linen and towels, it's your base for the perfect Kangaroo Valley escape. A 5 minute walk from the village centre and 50m from the cycle and walking path, it's the perfect location too. Coffee machine, record player and provisions included.

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.

Stroll to Bowral, Cherry Tree Walk, Mt Gibraltar

This newly-renovated, light, private guest suite is in a quiet area, in walking distance of pool, cafes, Bowral town centre and train station. If the Cherry Tree Walk and bush walks up Mount Gibraltar are appealing, this is for you. You will have separate access into a comfortable lounge room. There is a gas fireplace. The kitchenette has a bar fridge, microwave, coffee and tea facilities. You have a private courtyard off the bedroom, which has a fan and air conditioner.

Oksana's Studio

We would like to welcome you to Oksana's Studio which is a newly renovated space with modern furnishings and fixtures. It opens onto a large and private outdoor living area where you can relax taking in the rural vista while having a BBQ or sitting by the fire after exploring the local beaches and national parks. The property is set in a peaceful, rural landscape with bushland and wildlife to explore. All within a short drive of Jervis Bay and surrounding areas.

The Little House - Pet friendly*/Mid-week special!

While 'house' might be a stretch for this cosy studio-style room, it does have separate facilities. There's a separate "kitchenette", shower and toilet. IT HAS ONE KING SIZE BED and ONE SOFABED. The sofabed is charged at an additional $20/night. The Little House has everything you need for a short stay in The Highlands! * The property welcomes gentle, well socialised pups. The Little House backyard is also shared by my super friendly dog and ewe!