Vacation rentals with a pool in Wollondilly Shire Council

Renovated, Large Open Plan House with Pool

* Separate Study * 4 bedrooms with built in wardrobes * 2 modern bathrooms * 2 large living areas * Modern Kitchen/Laundry * Outdoor entertainment area * Swimming pool * Ducted Air-conditioning/Heating Looking for a home away from home, business or a family needing short stay accommodation with convenient facilities for the kids, this location is fantastic. STRICTLY No PARTIES- Noise complaints are taken seriously and not tolerated by myself or the Neighbours as this is a family neighbourhood.

Location · Family · Indoor spaces

Lux Thirroul Escape Pool, Heated Spa Theatre Room

A masterpiece of Moroccan inspired design, in a lush coastal setting .This multilevel home is unique. It is an oasis like no other, private balconies off most rooms, with a luxe relaxed ambience. The home boasts light filled living spaces, a new chefs kitchen with everything you could possibly need for a wonderful holiday or a weekend getaway. Lots of separate areas for your group, including a separate TV room as well as our huge movie theater room/games room with a state of the art projector.

Value · Family · Access

Relaxing Thirroul Home with Beach View

This spacious home sleeps up to 13 guests, making it perfect for group getaways and extended family holidays. Just a scenic 15-minute walk from the beach, you can enjoy the beautiful Thirroul neighbourhood along the way. The property features a large front and back garden, a pool, a balcony with an ocean view, and a gazebo with an outdoor dining area, fire pit, and pizza oven. Inside, the modern open layout fills the home with natural sunlight, creating a bright, comfortable, and relaxing stay.

Family · Location · Sleep quality

2 Bedroom Farmstay w/Giant Pool, Fire Pit & More

Large private apartment with a kitchen and bathroom on a 20 acre hobby farm. King Bed, Queen Bed, King Single trungle bed (2 beds) Giant heated undercover pool, poolside dining and bar, fire pit, outdoor equipment and animal experiences I have renovated some rooms provide income for my parents retirement. This is not a hotel or a brand new investment property, please don't expect perfection from my farm house. Farmstays come with animals which means animal noises and smells sometimes too.

Value · Location · Pets

Contemporary Oasis | Relax, Entertain, Events

✨ Grand Luxury Retreat with Pool & Pavilion, Perfect for Events Experience modern luxury in this expansive 4-bedroom home in Bradfield, minutes from the new Western Sydney Airport. Boasting a gourmet kitchen with butler’s pantry, sophisticated living spaces, & private master suite. Outside, a sparkling pool, elegant pavilion, and landscaped gardens create a refined resort-like atmosphere. Ideal for families, groups, or unforgettable events including weddings, parties, and hens celebrations.

Value · Hospitality · Checkout

Peaceful Countryside Estate

This is a nature lover's dream countryside escape, set on peaceful acreage surrounded by greenery. With spacious living areas, a games room, and a heated pool, this property offers the perfect base for relaxing, entertaining, and reconnecting with the outdoors. Ideal for families, groups, events, or anyone seeking a tranquil rural retreat with plenty of space to unwind. Also home to a resident horse, goats & chickens, and the property borders the Dharawal National Park and Georges River.

Family · Pool · Kitchen

Camellia Cottage Farm Stay

Lavinia & Matthew have been hosting guests on their property for 15 years. You will have this entire Camellia Cottage to yourself, it is 3 bedrooms all with queen size beds and 2 bathrooms situated on 5 acres of farmland. Thirlmere is a small semi-rural town in Wollondilly Shire. Popularly known for its railway origins, located 89 km of Sydney 60-minute drive. Wollongong is (50min) away and also close to Southern Highland (40min). Thirlmere won bronze in the small NSW tourism town award.

Family · Location · Accuracy

Luxury Stay with Heated Pool 8 guests 4 Beds

Step into modern luxury at this brand-new Hampton-style designer home. Perfect for families or groups, this stylish retreat comfortably hosts up to 8 guests across 4 beautifully appointed bedrooms. Designer interiors with hand-picked CoCo Republic furniture Bright, open-plan living with high ceilings and premium finishes Fully equipped chef’s kitchen with quality appliances Private outdoor space ideal for relaxing or entertaining Tranquil location in a quiet, upscale neighborhood

Location · Family · Sleep quality

Nature Meets Luxury| Pool

Welcome to your luxury countryside escape! The spacious house comfortably sleeps 10+ guests, offering plenty of room to relax. Enjoy the private swimming pool, home theatre, and multiple indoor & outdoor living areas. The home is beautifully furnished with high-end finishes and surrounded by peaceful nature. Please note there are steps at the entrance. Nearby, enjoy hot ballon rides, a top golf course, Gourmet dining... Perfect for family getaways, retreats, or a tranquil escape.

Location · Value · Layout

Luxury Nature-Surrounded Estate House With Pool

Welcome to your serene country escape in scenic Theresa Park. Designed for small families or couple getaways, this spacious four-bedroom residence blends finishes with complete relaxation. Unwind on the private balcony around the gas BBQ, take a refreshing dip in the outdoor pool, or gather in the sun-drenched living areas. Featuring keyless owner assisted check-in, premium underfloor climate control, and high-speed Starlink Wi-Fi, every detail ensures a seamless, high-end stay.

Location · Condition · Cleanliness

Farmhouse studio @ The Barn Stormhill sleeps 2

Chill by a cozy fire in winter or stargaze at night. Our Farm Pool Studio . Luxury is like entering a serene haven where indulgence meets tranquility. Nestled outside of Picton NSW. Just 1 hour from Sydney, it invites you to wake up to stunning sunrises in a comfy king-sized bed, savour breakfast from local produce, stroll through the orchard, immerse yourself in wildlife , soak in a bath, lazy by your private 17 mtr infinity pool. Its your time to breathe deeply & relax

Location · Pets · Comfort

Glen Alpine Home 5BR with Outdoor Pool

Discover elevated comfort in this beautifully appointed 5-bedroom, 2.5-bath executive residence located in prestigious Glen Alpine. Ideal for business travelers or discerning guests, the home features multiple workspaces, high-speed WiFi, and elegant interiors. Unwind by the private pool or host meetings in spacious lounge areas. Just minutes from Campbelltown Golf Club, shopping precincts, and transport links—this is refined living at its best.

Location · Value · Pool