Villa vacation rentals in Southern Highlands

Design lover’s Estate - sleeps 22

Built in the early 1900s, this impressive, large home equipped with heating, fireplaces, sauna, natural pool, outdoor entertaining, electric car charger & kitchen garden located in Moss Vale is ideal for large groups due to its multifaceted layout. Consisting of two seperate houses with their own kitchen and bathroom/s, the property also has a fully equipped cabin overlooking the park with bunk room for kids where pets can be accommodated and is just two minutes drive into the town of Moss Vale.

Family · Location · Parks

Adrift. Contemporary beachfront luxury.

Directly opposite Hordern's Beach, discover Adrift's contemporary, spacious & light-filled pavilion-style accomodation. Enjoy breathtaking beach views & spectacular sunsets from the balconies. Brand new carefully-curated furniture & furnishings throughout. Steps to the sand, local cafes & shops. Gentle walking distance to Gunyah & Jibbon Beaches, bushwalks, whale watching & to Bundeena wharf for a ferry ride to Cronulla. Only an hour from Sydney, you'll be adrift the moment you open the door!

Location · Nearby · Condition

Noms Ryokan

Nom’s Ryokan (in Japanese means traditional inn), is a private semi-detached 2 storey villa nestled between an awe-inspiring escarpment and a stunning beach in Stanwell Park. Located 150m from the beach or Baird Park, 600m to the local cafes with access to the iconic Grand Pacific Walk right on your doorstep (about a 4km walk to the Sea Cliff Bridge). Enjoy a coastal escape, connect with nature, treat yourself to local tastes, adventure with plenty of activities in the region or simply relax.

Value · Family · Bathroom

Amaroo Valley Springs Luxury Stays - Highcliff

Highcliff Luxury Villa. Exceptional Views & Ultimate Comfort. Adults Only. Welcome to Amaroo Valley Springs, an adults-only retreat in the Southern Highlands — the perfect place to relax and unwind whilst enjoying spectacular views and ultimate comfort. Highcliff is a 1-2 bedroom luxury villa for up to 4 guests, featuring king-size beds and offering everything you need for a memorable stay—you may never want to leave... We look forward to welcoming you. See you soon... Andy & Mark

Value · Location · Decor

Fig View | Luxury Coastal Vineyard Villa

Escape to Crooked River Estate—where vineyard views and rolling landscape meets the Pacific Ocean. Wake up above the vines with the sunrise over the ocean and unwind with a glass of wine as the sun sets over the valley. Fig View is a private villa with its own plunge pool, expansive deck and sweeping views across the vineyard, valley and ocean beyond. Designed for couples, family or small groups, it’s the perfect place to unwind, explore and reconnect.

Family · Location · Pool

Kaya @ Jingella - EcoLuxe Villa - Kangaroo Valley

Jingella Estate, Kangaroo Valley offers new luxury accommodation with stunning views from every room and a unique off-grid experience on 146 acres incl. private golf course, nature walks & wild swimming in our private creek rock pool. KAYA is a 2 bedroom villa sleeps up to 4 Rate is for one bedroom unless you book for 3-4 King beds unless you ask to split them at booking time Ensuites Covered patio Log fire Firepit Aircon TV Wifi BBQ Towels&linen

Value · Location · Kitchen

Wattamolla Lodge

Our lodges offer a private, self-contained getaway in the midst of the beautiful countryside, just 10 minutes drive from historic Berry village. Each lodge has been thoughtfully positioned in a secluded spot within the stunning grounds of The Drawing Rooms of Berry, nestled on Woodhill Mountain and close to the famous Drawing Room Rocks bushwalk. Each lodge offers 2 bedrooms, 2 bathrooms, a kitchen, dining and living area, along with a mini laundry.

Family · Value · Walkability

Hampton's" on Henley

Escape to coastal luxury in this elegant Hamptons-style 3-bedroom villa, perfectly positioned in the heart of beautiful Kiama. Just a 5-minute stroll to Kendals and Surf Beach and 10 minutes to cafés, boutiques, restaurants and the famous Kiama coastline. Featuring stylish interiors, spacious living areas and modern comforts, this sophisticated retreat is the perfect base for families, couples or friends seeking a relaxing seaside escape.

Value · Family · Walkability

AVALON at HUSKISSON

Fully self contained NEW MODERN villa with own parking at entry and seperate driveway. Comfortable KING BED with luxurious white linen. Large living room, kitchenette, bathroom with bath sheets, fully equipped laundry, outdoor area, air conditioning and ceiling fans FREE WI-FI. A 5 minute walk to the main street (Owen St) Huskisson, which is home to Husky Pictures, Boutique Shops, Cafes, Restaurants, Clubs & The Famous Husky Pub.

Value · Location · Beach

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.

Value · Family · Layout

Woonona Beach Villa Family & Pet friendly.

Family & Pet friendly Villa 5 min walk to the Beach Close to Panorama House Wedding Venue. Enjoy the Beach, Cafes & Parks while staying in a Modern, Super Clean, Beach Villa Private with FREE Parking onsite Woonona Beach & Rock Pool, Cafes & Park a short 5 min walk 1 min walk to train station with easy access to Airport, City, Uni & Wollongong City Groceries, Post Office, Bottle O, Bakery Newsagent, Fish n Chips 2 min walk

Location · Value · Parks

ARUNA Estate Luxury Farm Villa

ARUNA Estate is a rural retreat, offering an escape from the everyday, just 90 minutes out of Sydney or Canberra. We have 4 Villas on the property, as well as 2 off-grid cabins, and offer a taste of the highlands with a generous hamper of local wine and produce. We run sheep and boast a 4-acre ‘no till regenerative’ garden, with local small-scale farmers, Two Birds Farm.

Family · Location · Breakfast