Vacation rentals with a pool in Wollondilly Shire Council

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wollondilly Shire Council

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Home in Silverdale

4.85 out of 5 average rating, 171 reviews

Somerset Manor Grand Mansion Luxury 5 - Star Stay

Somerset Manor Grandeur Millionaire Home, Two Living Area Spacious, Exquisitely Furnished, Luxurious, Fully Equipped Home away from Home. Quality Beds -Tempur Mattress, Quality Furnishings, 5G Fast Wifi, Netflix,15 minutes Drive to Penrith, Base of Blue Mountains, Work Stay, Family Stay, Overseas Stay. Covered entertainment areas, Wood Fireplace, Daikon Air Con, New Weber BBQ, Hot Spa Vortex Hydrotheraphy. Easy drive to Sydney CBD & Blue Mountains, Brilliant Location to Visit Sydney. AIRBNB LUX

Guest favorite

Farm stay in Theresa Park

4.79 out of 5 average rating, 42 reviews

2 Bedroom Unit in the Australian Countryside

Large private apartment with a kitchen and bathroom on a 20 acre hobby hobby farm. King bed, Starlink internet, big desk, giant indoor pool (available 10am-4pm) Plenty of clothes storage, closet and tallboy. 2nd room adjoining main room for bookings of 3-4 people. This isn't a brand new renovated for profit airbnb or a hotel. This is a separate area in our family home. You share the entrance to the home with us. There are sheep, baby cows, goats, dogs, chickens, quails, cats and dogs here.

Guest favorite

A refreshing swimming pool is set within a landscaped outdoor area, surrounded by a low wooden fence and natural greenery. Sunlight reflects off the water's surface, creating a vibrant blue hue, while a spacious lawn offers additional space for relaxation.

Home in Mount Annan

4.85 out of 5 average rating, 181 reviews

Renovated, Large Open Plan House with Pool

* Separate Study * 4 bedrooms with built in wardrobes * 2 brand new bathrooms * 2 large living areas * Modern Kitchen/Laundry * Outdoor entertainment area * Swimming pool * Ducted Air-conditioning 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.

Guest favorite

A tranquil outdoor space features a lap pool surrounded by manicured grass and palm trees. Comfortable lounge chairs are positioned nearby for relaxation. The warm colors of the textured walls contrast with the cool blue of the pool, creating a serene atmosphere for enjoyment.

Home in Thirroul

4.9 out of 5 average rating, 40 reviews

Luxe Thirroul Holiday Home, Pool&Spa Home Theater

A masterpiece of Moroccan inspired design this multilevel luxurious home is truly unique. An oasis like no other, full of character and relaxed ambience, for all who stay. The home boasts light filled living spaces, a new kitchen with everything you could possibly need for an amazing stay. Also a huge retreat/games/cinema room, 5 bedrooms, 4 bathrooms, pool, spa, built in BBQ with expansive escarpment views, partial ocean views from the upper balconies, the list goes on! 4 parking spots.

Superhost

The exterior of the home includes a sparkling swimming pool surrounded by a stone patio and landscaped foliage. The two-story structure features large glass doors leading to the interior living spaces, with a balcony above offering additional outdoor enjoyment.

Home in Thirroul

4.74 out of 5 average rating, 34 reviews

The Birdhouse in Thirroul

This stunning home is a delight, perfect for relaxing family holidays, nestled on the edge of Thirrouls escarpment only a short drive to Thirroul Village and Beach. Entertain the kids in the pool or on the play equipment. Containing a fully equipped kitchen, spacious open plan dining, living and outdoor areas. Sleeping 10 guests in 5 bedrooms including a large open plan master with ensuite. Take in the serenity of the bush and checkout the local bird life. Bed linen and towels provided.

Guest favorite

An outdoor space is depicted, featuring a refreshing pool surrounded by a glass barrier. The landscaped area includes artificial grass, a modern seating arrangement, and a fire pit. Lush green plants are arranged along the perimeter, enhancing the tranquil ambiance.

Home in Gledswood Hills

5 out of 5 average rating, 9 reviews

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

Home in Glen Alpine

5 out of 5 average rating, 4 reviews

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.

Top guest favorite

Farm stay in Picton

4.99 out of 5 average rating, 74 reviews

The Farmhouse Pool Studio , The Barn Stormhill

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

Guest favorite

A charming cottage exterior is shown, featuring a natural brick façade and a light-colored roof. Large windows allow natural light to enter, while a vibrant tree with purple flowers stands nearby, surrounded by greenery. A gravel driveway leads up to the entrance.

Home in Thirlmere

4.93 out of 5 average rating, 28 reviews

Entire Camellia Cottage Pet Friendly

Your hosts are Matthew & Lavinia who love hosting guests on their property. You will have this entire cottage to yourselves. **Please note this property is pet friendly however only 1 pet is allowed to stay and they can't be left alone at any time (No Cats). Thank you** The cosy cottage has 3 bedrooms all with queen size beds and 2 bathrooms on 5 acres of farmland. We grow fruit trees, herbs, vegetables with loads of ornamental flowers/trees.

An outdoor dining area features a wooden table surrounded by six white chairs, situated beneath a covered patio. A shaded lounge area with a wooden table is nearby, showcasing a well-manicured lawn and a glimpse of the in-ground pool in the background.

Home in Cobbitty

4.8 out of 5 average rating, 5 reviews

Hamptons Haven in Cobbitty

Located in the picturesque Cobbitty area, our home is just a short drive from beautiful parks, local markets, and charming cafes, making it an ideal base for discovering all that the region has to offer. Whether you want to relax by the pool, enjoy alfresco dining, or explore the nearby attractions, our modern custom-built home offers the perfect sanctuary for your getaway for you and your pets. Your escape to comfort and style awaits!

Superhost

An aerial view captures the expansive layout of the property, showcasing multiple buildings that blend seamlessly into the landscaped grounds. Lush greenery surrounds the structures, along with a central infinity pool and spa, highlighting the tranquil setting of the estate.

Home in Picton

The Grange

Escape to an unforgettable getaway at this stunning property nestled within the idyllic Nangarin Vineyard Estate. This luxurious retreat is perfect for family vacations, romantic escapes, or group retreats, offering a blend of elegance, comfort, and endless entertainment options. Positioned on nearly 2 acres of beautifully landscaped grounds, this private escape promises a resort-style experience you’ll never forget.

Home in Mount Pritchard

4.75 out of 5 average rating, 4 reviews

Holiday with The Pool

Modern 2-bedroom granny flat offering comfort and convenience in a quiet street. Features spacious bedrooms with wardrobes, a fully equipped kitchen, large air-conditioned living area, and a bathroom with shower. Private entry ensures your privacy. Close to Liverpool CBD, Cabramatta’s vibrant food scene, shops, and public transport. Perfect for families, couples, or business travelers. Book your stay today!