Pet-friendly holiday rentals in Southern Highlands

Little Gem at Retford Park Estate. Bowral-5 Min

New apartment located in the prestige "Redford Park Estate" a walk away to the heart of Bowral or 2 min drive to its Restaurants, cafes, boutiques, parks, museums, galleries, vineyards and golf courses.Also 5 min walk within the Estate to visit the Regional Gallery & cafe and explore the stunning gardens and House at "Retford Park", National Trust. The space it is modern, airy , relaxing and stylish. Main bedroom- King bed. Living with large queen sofa bed. Warm and cosy, just come and relax

Pets · Outdoor spaces · Family

Clanoc Cottage a cosy, rustic, Highlands Retreat

Welcome to Clanoc Cottage a 5-minute stroll from the heart of Berrima Village. An ideal base for couples, friends, or families wanting to relax, explore, and enjoy the charm of historic Berrima and the Southern Highlands. The cottage features two Queen beds and a King Single with trundle—each made up with lovely linen and electric blankets for cosy comfort. Enjoy a brand-new bathroom, a well-equipped kitchen perfect for cooking and entertaining, & a spacious yard ideal for relaxing outdoors.

Pets · Walkability · Condition

Unique'Danglestone' Couples Hideaway in the Forest

Awe inspiring views surrounded by nature. Nestled in the lush greenery of a private forest this modern architecturally designed cabin is luxury at its best. With the warmth of the heated floor & indoor gas fire you will be toasty warm all year round. Sutton Forest is very near several vineyards and villages. An ideal location to escape the city. PETS allowed but please disclose when booking- Max 2 people only (not suitable for infants) 1 Queen bed only MASSAGE available nearby (plse ask)

Walkability · Pets · Cleanliness

'The Bower' Stylish garden bungalow Mount Kembla

'The Bower' is located in lush gardens in the historic village of Mt Kembla. This stylish bungalow is the perfect relaxing retreat or home base to explore the Illawarra and South Coast. Walk to the Historic Mount Kembla Hotel for dinner and a drink or explore the many bush walks located in and around the area. Wake up amongst the trees and end your evenings relaxing on the large deck or around the fire pit. Only fifteen minutes away from Wollongong CBD or beautiful beaches of the area.

Walkability · Pets · Backyard

Contemporary Country Experience

Contemporary country experience Enjoy the simplicity and restoration that rural peace offers without getting your hands dirty (*unless you want to!). This design inspired cottage provides a place for up to 6 people to take in the sunset sitting by the open fire, then wake to collect fresh eggs and watch the horses, cows and kangaroos graze, or wander down to the creek for a picnic. The cottage is fully enclosed in a fenced area 800m2. We have changed the fencing so none is electric.

Outdoor spaces · Walkability · Indoor spaces

Fantoosh

Welcome to your blissful getaway! This beautifully designed picture-perfect cottage is nestled in the heart of Sutton Forest, the ideal fit for anyone looking to relax and unwind. Enjoy the heated floors and an Internal fire at the press of a button. Firepit outside awaits, sizzle a steak or toast marshmallows under the stars. Snuggle up on the couch, stream a movie you never got to see or work on the super fast internet. Take a walk along the country lanes and enjoy the fresh air.

Walkability · Pets · Breakfast

The Carriage House at Welby Park Manor

The Carriage House at the historic homestead, Welby Park Manor has been lovingly restored and renovated. Oozing with character and charm, the Carriage House is self-contained, private, dog-friendly and fully fenced. On-site parking is available, wood is supplied for the slow-combustion fireplace and outdoor fire pit. you will be welcomed with drinks on arrival. Need extra accommodation? please look up The Chapel, (on the same property), on Airbnb.

Outdoor spaces · Pets · Value

Southern Highlands Get-a-Way —Breakfast Supplies—

A pet friendly, comfortable and well-appointed, self-contained apartment for rent amongst the gum trees. Only a short walk to Mittagong train station, Sturt Gallery, shops, restaurants and galleries. Newly renovated, the apartment has reverse cycle air-conditioner, a private entrance, designated parking area and a private outdoor outlook. Wi-fi and Netflix all included. Comfortable, private, quiet get-a-away so stay a week or more. No cleaning fee.

Walkability · Pets · Indoor spaces

The Villa @ The Vale Penrose

Set on five acres of beautifully landscaped grounds in the Southern Highlands, The Villa @ The Vale Penrose is a refined country escape designed for couples seeking space, privacy, and understated luxury. Part of The Vale Penrose—an established boutique farm stay welcoming guests since 2019—the Villa offers a balance of contemporary design and rural tranquillity, with expansive interiors and uninterrupted views over rolling hills.

Walkability · Pets · Accuracy

'Rosevilla' in Berrima.

Built in 1883, this gorgeous historic cottage is right in the heart of Berrima village, within easy walking distance of exceptional restaurants and cafes, quaint local shops, historic buildings, the beautiful river and Australia's oldest continually licensed inn. Bendooley Estate is only a 5-minute drive away, making the cottage an ideal choice for wedding guests. Numerous wineries and Berkelouw Book Barn are all close by.

Walkability · Outdoor spaces · Decor

The Lazy Duck, Bundanoon

The Lazy Duck is just 300m walk from the center of town yet has a feeling of being on top of the world. Stunning views over the Morton National Park from one of the highest points in town. Looking into Kangaroo Valley. It is right next door to Osborn House, on its own private fenced block. The cottage is nestled in the trees with a huge picture window. You won’t forget your time in this romantic and memorable place.

Walkability · Outdoor spaces · Heating

Vineyard Stay, Designer Barn

Architecturally designed barn on a working farm and vineyard in the picturesque village of Exeter in the Southern Highlands. Dawning Day Farm has everything you need for a relaxing country getaway, just 90 minutes' drive from Sydney. Enjoy a wine tasting in the adjacent cellar door (Fri-Sun), feed the sheep and alpacas, then light the fire and settle in for a movie night on the 110-inch big screen home theatre!

Pets · Walkability · Sleep quality