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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Guest favorite

A spacious foyer features a vibrant area rug with intricate patterns, complemented by decorative furniture. Large glass doors provide views into the adjoining living spaces, which are illuminated by natural light. Exposed brick walls enhance the welcoming ambiance of the entryway.

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

A spacious room features a comfortable bed, a window allowing natural light, and a wooden floor. A sitting area includes a chair and desk, while a dresser provides additional storage. Soft curtains frame the large window, enhancing the room's relaxed ambiance.

Farm stay in Theresa Park

4.8 out of 5 average rating, 45 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.

Superhost

Home in Bradfield

New place to stay

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.

Top guest favorite

A spacious bedroom is presented with a large bed covered in a patterned blue and white quilt. Two windows allow natural light to fill the room, accompanied by a small bedside table and a decorative plant enhancing the calming environment.

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

An inviting outdoor space is highlighted by a turquoise pool, surrounded by lush palm trees and modern landscaping. Soft outdoor lighting creates a welcoming atmosphere, casting gentle reflections on the water. Comfortable seating areas are positioned to enjoy the serene views.

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.

Superhost

A spacious dining area features a large marble table surrounded by comfortable chairs. A stylish chandelier hangs above, illuminating the room. In the background, a modern kitchen is visible, equipped with dark cabinets and a large island with seating.

Home in Gledswood Hills

4.91 out of 5 average rating, 11 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

A spacious two-story house is set amidst lush greenery and colorful flowers. The entrance is framed by well-kept gardens leading to a set of steps. A vibrant sunset fills the sky, adding warmth to the scene.

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

A serene infinity pool reflects the surrounding greenery, framed by a wooden deck. The nearby house features large windows and a spacious outdoor dining area, inviting relaxation. Lush trees provide shade, enhancing the tranquil atmosphere of the setting.

Farm stay in Picton

4.99 out of 5 average rating, 75 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

The exterior of a two-story yellow home is shown, set against a blue sky with scattered clouds. The house is surrounded by green grass and features stone steps leading up to a balcony with plants on either side.

Farm stay in Picton

5 out of 5 average rating, 7 reviews

The Vines

Welcome to our humble abode, The Vines, Picton. Situated on an acre, overlooking one of Wollondilly’s finest vineyards. This beautiful home is a little slice of paradise as we like to call it. Offering accomodation for 10-12 people (7 beds + sofa bed), the perfect home for a family getaway or an escape from the city. A designated game room downstairs for the kids and adults, a pool and spa for the warmer days, enjoy the outdoor fire pit in the evenings with the family.

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.

A light-filled living area features a soft beige sectional sofa adorned with blue and gray pillows. A glass-top coffee table sits on a decorative area rug, and sheer curtains frame panoramic windows that offer a view of the outdoors.

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!