Sit back, relax and watch the world go by from your very own private yacht. You’ll want to spend most of your time on the upper deck with a glass of wine and a cheese platter for company – but there’s always a lounge with a dining table and leather sofas waiting inside, as well as a queen size bed and two bathrooms (one ensuite). If you’re ever in the mood for some activity, you can go paddle-boarding, kayaking, fishing, snorkelling or hiking on the island. Tailored sailing tours area also available for an additional charge.
Set in the Blue Mountains, in the settlement of Bilpin, this Airbnb looks like something JRR Tolkien might have dreamt up. The glamping-style cave wouldn’t look out of place next door to Bilbo Baggins’s house in Hobbiton, but it’s a very real property you can stay in – if you’re lucky enough to find availability. For your money, your rock-carved abode offers a luxury spa bath, a log burner for romantic nights, one cosy double bed and even a flatscreen TV if you get bored with the stunning mountain views – but we think that’s highly unlikely.
On the one hand, The Little Black Shack is a literal – and accurate – description of this two-bed fisherman’s cottage, but it doesn’t tell the full story. Though only a mile from the mainland and Palm Beach, it might as well be a million miles away. Getting there is part of the experience: take the old timber ferry from Palm Beach, then make your way up a short walking track at the end of the beach or over the rocks along the beach at low tide. You can swim and snorkel in the clear waters lapping the beach, or go fishing off the rocks below. Kayaking and sailing is also possible, while the surrounding National Park offers some incredible bush walks to more secluded beaches.
Lining the shores of Pittwater in the small community of Clareville, this freestanding boathouse has direct access to the waterfront, with two single-person kayaks available to use at your leisure. In the evenings, relax on the sundeck and fire up the BBQ to dine al fresco. Inside, you’ll have all the facilities needed for a comfy stay – from the double bed and bathroom to the well-equipped kitchenette, dining table, lounge and TV.
Located above a working art studio in the trendy inner-west neighbourhood of Marrickville, this Airbnb, which sleeps two, is an airy space on the first floor of an old warehouse that began life as a bakery in 1985. The massive space includes a turntable with a few hundred records from the 1970s and 80s, as well as a veggie garden, chickens and a hammock in the back yard. It’s a 15-minute train ride into the city, and the station is a few minutes away on foot – though you may well find the quiet, slow-paced lifestyle and multicultural vibes of Marrickville a little more to your liking.
The rusted corrugated iron exterior doesn’t look like much from the outside, but the Shed is not what it seems. Crafted out of recycled and reclaimed materials – right down to the door handles and bathroom fittings – this machinery shed-turned-luxurious eco-haven, which sleeps eight, includes a rustic fireplace surrounded by comfy sofas, a farmhouse-style dining table and a fully equipped kitchen complete with a wood-fire pizza oven and BBQ. You can pick your own herbs from the garden and collect free-range eggs from the chickens for breakfast. And you get direct access to the Kangaroo Valley, an idyllic picnic spot with waterfalls and wildlife.
There are luxury villas, and then there is Keanu. Located on the clifftops of Whale Beach, this open-plan beach house provides the ultimate seaside getaway in Sydney. You and up to 11 of your friends or family members will sleep comfortably here, thanks to all the spacious bedrooms – but the biggest draw is undoubtedly the solar heated outdoor pool, overlooked by balconies above. For privacy, escape to the studio below the pool deck, or leave it for the kids – there are two single beds, a bunk bed, a bathroom and a kitchenette.
Though it may only be a private room and not an entire place, this listing is very rarely available – so if you’re in luck for your preferred dates, don’t hang about. Hosts Vinh and Stuart were among the first Airbnbers in Sydney and they’ve established themselves as one of the best places to stay in the city (just read the reviews) – such is the volume of enquiries they receive, they’ve even hidden a code word in the description of their listing to filter out anyone who can’t be bothered to read. Breakfast is offered every morning, from seasonal fruits to bread, tea, espresso coffee and “all the Vegemite you can handle”. Now there’s an incentive if we ever heard one.
Get cosy in this slice of the Wild West in Hunter Valley, the renowned wine-growing region two hours north of Sydney. Sleeping up to 10 guests, Walkers Run is decorated with knick-knacks that would look more at home in New Mexico than New South Wales. It’s situated on 30 acres (12ha) of private land, bristling with kangaroos, wallabies, wombats, goannas, birdlife and other native species. Keep your eyes peeled for Kenny the Koala, who occasionally visits during the mating season.
This is an updated version of an article originally written by Tom Smith