Holiday 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, 172 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

Superhost
A modern living area features two sleek armchairs and a low coffee table, with soft upholstery and a minimalist design. Floor-to-ceiling glass doors provide a view of a softly illuminated pool, while elegant lighting fixtures add a touch of warmth to the space.
Home in Gledswood Hills
4.74 out of 5 average rating, 58 reviews

Hampton Designer House 4 bedroom +Heated Pool

Discover the charm of Hampton-inspired living at this stunning brand-new designer home in Gladeswood Hills. 🏡✨ Designed with both style and comfort in mind, this spacious 4-bedroom residence is perfect for families, friends, or business travelers looking for a touch of elegance. 💎 Highlights you’ll enjoy: 4 stylish bedrooms with plush double beds – sleeps up to 8 guests Elegant interiors featuring CoCo Republic designer furniture Peaceful neighborhood offering both privacy and convenience

Guest favourite
An aerial view reveals a spacious family home surrounded by lush greenery and open land. The property features a wide driveway and nearby structures, with trees adding a natural ambiance to the setting.
Farm stay in Theresa Park
4.84 out of 5 average rating, 57 reviews

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.

Superhost
Home in Bradfield

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.

Guest favourite
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
4.84 out of 5 average rating, 194 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.

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
4.88 out of 5 average rating, 50 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, 35 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 favourite
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, 18 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.

Guest favourite
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.

Top guest favourite
Home in Wallacia
4.95 out of 5 average rating, 21 reviews

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.

Top guest favourite
Home in Camden
4.98 out of 5 average rating, 41 reviews

Charming country cottage

This hidden 4-bedroom cottage in Camden is a private oasis with scenic gardens, a large deck, a saltwater pool, and nearby river tracks. It offers a peaceful escape to a historic town, making it perfect for relaxation and outdoor adventures. The fully equipped kitchen and unique succulent garden add extra charm.

Superhost
Four decorative bunny figures are positioned near a tree, each wearing bright yellow outfits with colorful accessories. The group includes a tall bunny with a basket and a smaller one sitting atop a wooden log, creating a cheerful outdoor scene.
Home in Mount Hunter
4.8 out of 5 average rating, 25 reviews

3BD Exclusive Manor Retreat Farm

Enjoy a tranquil retreat with your family at this serene countryside getaway. Immerse yourself in the calmness of nature and experience the charm of rural living, far from the city’s noise and rush. Yet, it’s conveniently located just a 15-minute drive from Camden and only an hour from Sydney city center.

Popular amenities for Wollondilly Shire Council rentals with a pool