Smoking friendly vacation rentals in Southern Highlands

Island break beach-house: Beachfront + POOL + SPA

Welcome to Island Break Beach House! EARLY CHECK-IN (11am) + LATE CHECK-OUT (2pm) with all bookings. Kick back and make the most of your stay in this architecturally designed, custom-built luxury beach house. Multiple entertaining zones, water views and the beach right across the road. Seamless indoor-outdoor living, two outdoor kitchens and a full-house Sonos system mean good vibes come standard. Summer fun is a given — but winter wins too with the hot spa, heated pool + cosy fireplace.

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.

Acres of Avoca

Hello we have a beautiful 5 acre property located in the Southern Highlands. We are fantastically close to Bowral and Robertson for wonderful food, markets and shopping. Kangaroo Valley is just a short scenic drive away and Shoalhaven, Jervis Bay and the coast only 45-55 mins down the mountain. There are cafes and wineries, shopping and great outdoor activities to be had. We are fond of our animals and have several sheep, 2 highland cows, Waffles the Groodle, a cat, lizard and chickens.

Tranquil country hideaway

Take it easy at this unique and tranquil getaway. Located in the southern tablelands NSW, just 10 minutes from the small country town of Marulan and 25 minutes from the historic town of Goulburn. Perfect for a restful weekend, you can choose to fill your day with bush walks, exploring the local shops, cafes and wineries or simply sit and enjoy a good book and the serenity by the outdoor fire. Furry friends welcome, fence around tiny home. Dams on property. Wood provided for fire pit.

Morton Park Rural Retreat

Tucked away amongst the gums tree, a cockatoo and a kangaroo, Aussie wildlife at its best: wombats, goannas, koalas, emus all in the comfort of your private, cosy, self-contained cottage, set on a 130-acre farm. Large covered veranda with outdoor dining. Pet friendly. NO HIDDEN CLEANING FEES. Plenty of on-farm activities, only 1.5 hrs from Sydney, 1 hr from Wollongong, 1.5 hrs from Canberra. In the heart of the Southern Highlands, so you can explore Bowral, Berrima, Bundanoon.

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.

Tiny House with Parkland Outlook

Fully furnished Tiny House. Modern compact living space with a full size fridge/freezer, Queen bed, convention/grilling microwave, electric hot plate and smart TV. Full size shower in spacious bathroom. Air conditioning and heating in open plan living space with dining space/work space. Large loft storage area, plenty of closet space and kitchen storage including large pantry. Off street parking in cul-de-sac street that is a short walk to CBD and local amenities.

Silver Birch Studio

Silver Birch Studio is perfect for an overnight or weekend stay in the Southern Highlands for up to 2 adults. This self contained studio has an en-suite, small kitchenette and a deck overlooking the garden. The peaceful location is less than three minutes drive to Mittagong town, which offers a number of great restaurants and cafes. Mittagong is also close to Bowral, Moss Vale and historic Berrima which all offer a variety of markets, art galleries and local wineries.

Farm "The Stockyards "3 Bed Views Foxground Berry

Stockyards is a 2021 build 3-bedroom farm stay in the picturesque valley. The property has fabulous views, a large, covered verandah , fire pit guests have to supply wood. Please extinguish fire pit before you leave it. Foxground is a coastal farming community The property is 5 minutes from the coastal towns of Berry and Gerringong. Children/infants under 12 not catered for. Please do not book. We do not offer the opportunity to charge EVs as we are on a rural grid.

Wake up to the ocean at LegaSea

LegaSea is a self contained Guest House overlooking the historic Shellharbour boat harbour and coastline. Guests will feel as though they are levitating directly over the glistening waters of the calm harbour and can observe the activity of the nearby village from a comfortable, luxurious space. Village cafes and amenities are a short stroll away, and the beach or famous cowries surf break is at your doorstep. Find us on Instagram @Legasea_shellharbour

The Hideaway at Sylvan Glen Estate

Romantic couples retreat | Outdoor bath | Southern Highlands escape Escape to your own private retreat in the Southern Highlands. Wake up to birdsong, soak in the outdoor bath under the stars, and spend cozy evenings by the fire pit overlooking the countryside. Less than two hours from Sydney and Canberra, it’s the perfect countryside getaway for a romantic weekend, anniversary or relaxing escape.

The Tailor's Terrace | Valley Views | Fire Pit

A beautifully designed architect home with sweeping escarpment views, rated 4.98 stars by 200+ guests and an Airbnb Guest Favourite. Sleeps 5 across 2 bedrooms – each with a private ensuite – plus a third bathroom, fire pit, BBQ deck, full laundry and a backyard. 81 Mbps WiFi. 100m to the village. Community pool across the road. Can be booked with The Tailor's Cottage for up to 7 guests.