Holiday 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.

Family · Value · Cleanliness

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.

Family · Value · Nearby

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 · Accuracy · Checkout

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 · Indoor spaces

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.

Pool · Hospitality

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 · Nearby

Lakeside Guest House

Luxury Golfside Retreat | Brand New 5‑Bedroom Home with Pool & Alfresco Dining Experience contemporary luxury in this, architect‑designed 5‑bed, 5.5‑bath home, perfectly positioned next to championship golf course and just a 100‑metre walk to the clubhouse. Designed for comfort, entertaining, and relaxation, this stunning residence offers expansive living spaces, premium finishes throughout, seamless indoor–outdoor flow and is ideal for families, groups, golfers, or executive stays.

Location · Bathroom · Cleanliness

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 · Pool

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 · Family · Amenities

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 · View · Condition

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 · Hospitality · View

Adam’s Hall 1900s School house

Adam’s Hall is a renovated 1900s cottage that was used as a School for 20 children in 1926. It shares some amazing history with its surround in Wallacia just a short walk from the well known Wallacia pub. The house itself is a charming mix of old character and new amenities with plenty to do for families and big groups. A 20 minute drive to Penrith or Narrellan. A 8 minute drive to the new Nancy-Bird Walton Western Sydney Airport.

Family · Value · Indoor spaces