Vacation rentals with a pool in Southern Highlands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Southern Highlands

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

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Top guest favorite
A spacious covered verandah features a large polished concrete table surrounded by comfortable seating. Lush greenery and panoramic views of rolling hills are visible in the background, providing a serene setting for relaxation.
Cabin in Kangaroo Valley
4.98 out of 5 average rating, 153 reviews

Nostalgia Retreat- Panoramic Views

Take in the extraordinary views from our comfortable one bedroom cabin adjoining the stunning Kangaroo Valley Golf Course. Nostalgia Retreat has a new queen size bed with quality bed linen ,wall mounted TV and claw foot bath.There is a separate shower, Air conditioning ,Foxtel and parking for two cars wifi Swimming pool ,tennis courts and restaurant are available for guests enjoyment . Kangaroos and wombats are on your doorstep . 5 Mins drive from KV village,cafes ,shops and historic bridge.

Top guest favorite
Two wooden lounge chairs are positioned on a grassy area, providing a view of the expansive landscape. Rolling hills and a gentle river can be seen in the distance, framed by lush trees and colorful foliage under a clear blue sky.
Home in Kangaroo Valley
4.98 out of 5 average rating, 122 reviews

Romantic hideaway at HAMPDEN HOUSE

This magnificent country home provides a blessed setting for an unforgettable Kangaroo Valley experience .The comforts of modern country living with all the charm of yesteryear .Your own private POOL,sun dried linen wood fire ,treats of French bubbly and locally handmade chocolates await you .WiFi,coffee machine ,three acres of gardens and lawns,RIVER FRONTAGE .Hampden House is only a 10 min stroll or bike ride to the village and get remains a peaceful little world of its own. PID-STRA-589

Guest favorite
A private pool is set within a landscaped yard, offering clear views of the ocean. Wooden decking surrounds the pool, with lounge chairs positioned nearby. Lush greenery and coastal vegetation create a serene backdrop against the sparkling blue water and gentle waves in the distance.
Guesthouse in Kiama Downs
4.93 out of 5 average rating, 280 reviews

Uninterrupted ocean view, private & quiet. Relax.

One of the only listings to have a pool in Kiama Downs. Pet-friendly, large space for 2 people with a kitchenette, fridge, combined dining, and living area with a bedroom with a queen bed. Inclusions on your stay are a coffee maker with coffee pods and teas, kettle, washing machine, microwave, cooktop, flat-screen TV, wi-fi, and Netflix. The pool is yours to use (not shared) with direct access to Jones Beach. No more than 2 medium sized dogs please. Please note unit is lower floor of house.

Guest favorite
A large stone outdoor bath is set against a backdrop of rustic wooden shutters. Soothing candles are placed nearby, and a natural wooden stool adds to the serene atmosphere. Soft lighting enhances the inviting space for relaxation amid nature.
Home in Kangaroo Valley
4.88 out of 5 average rating, 348 reviews

The Treehouse Kangaroo Valley on Kangaroo River

The Treehouse offers picturesque Glamping perched over Kangaroo River in the Heart of Kangaroo Valley. It has a beautiful large stone outdoor bath to soak in set amongst the canopy of the gum trees. The Treehouse Kangaroo Valley sleeps up to 4 adults(2 couples) or really close friends & is an ADULTS ONLY retreat. We offer great value as we use Airbnb Smart Market Pricing. PETS: considered on application only. Enquire PRIOR TO BOOKING for our T and C to see if your pet qualifies.

Top guest favorite
An ornate black metal gate stands open, framed by stone pillars. Beyond the gate, a gravel driveway leads toward a charming building surrounded by well-kept gardens. A friendly Newfoundland dog is visible at the gate, providing a welcoming presence.
Guesthouse in Bowral
4.92 out of 5 average rating, 160 reviews

The Annexe at Beatrice Park, Bowral

Welcome to The Annexe at Beatrice Park Perfect for Couples or Solo Traveller’s ASK ABOUT OUR SPECIALS Nestled within the heritage-listed gardens of Beatrice Park, The Annexe offers a private retreat ideal for a weekend escape or an extended stay. Whether you're here for leisure or business, you’ll find The Annexe a tranquil and comfortable home away from home. Don’t BELIEVE US - Read our reviews

Guest favorite
A custom-built cabin is partially visible among tall Australian Scribbly Gums. A wooden deck features a chair, inviting relaxation in a serene outdoor setting. A fire pit surrounded by logs is located nearby, adding to the rustic ambiance.
Farm stay in Penrose
4.88 out of 5 average rating, 126 reviews

ARUNA Estate off-grid cabins

ARUNA Cabins provide the ultimate off-grid experience. Nestled amongst the Australian Scribbly Gums, it offers a bush view, down to the River. If you want to get as far as possible from the bustling world, the ARUNA cabin is for you. Custom built for their bush location, our cabins provide a stylish and snug escape. They are completely off grid so you can ensure your total freedom from the everyday.

Top guest favorite
A modern swimming pool is seen with clear blue water, surrounded by a stone deck. Comfortable outdoor seating is positioned nearby, offering views of the lush green landscape and trees beyond, enhancing relaxation in a serene outdoor setting.
Home in Bundanoon
4.91 out of 5 average rating, 151 reviews

Kalamunda Estate with Pool, Fire Pit & BBQ Deck

Kalamunda Estate is a spacious retreat set on 5 acres, just 3 km from Bundanoon. Perfect for large groups, it features a pool, a large outdoor BBQ deck with stunning bushland views, and a games room. The 5-bedroom house accommodates up to 11 guests, making it ideal for family gatherings or friends' get-togethers. With a vast garden, there’s plenty of room for kids to play and enjoy the outdoors.

Guest favorite
A spacious outdoor area features lush green grass and a private plunge pool. Countryside views showcase rolling hills under a clear blue sky, with a timber deck nearby. The glass fencing ensures a safe and tranquil environment for relaxation.
Cottage in Meroo Meadow
4.94 out of 5 average rating, 189 reviews

Mercer Cottage at Silvermist Farm South Coast

Mercer Cottage at Silvermist — a light-filled, contemporary retreat with vaulted ceilings, designer touches, and sweeping mountain views. Relax on the sun deck, dine outdoors, take a dip in your private plunge pool, and unwind by the fire pit. Perfectly located between Berry’s boutique cafés and the golden sands of Seven Mile & Gerroa Beaches.

Top guest favorite
An aerial view captures a spacious property surrounded by green fields. The structure features a modern design, with a clear driveway leading to the entrance. A pool is visible in the backyard, complemented by mature trees and landscaped areas.
Cottage in Moss Vale
4.97 out of 5 average rating, 100 reviews

Moss Vale 2 Bed Cottage

Kick back and relax in the beautiful Southern Highlands in your private newly refurbished cottage set in our lovely acre of land. Conveniently located for all the historic villages and vineyards that this area has to offer. Unwind with a spa at the end of the day, or simply enjoy a glass of local wine in front of the fire.

Top guest favorite
A charming cottage is set amidst lush greenery, featuring a covered porch with outdoor seating. Large windows allow for ample natural light, and a welcoming front door is framed by plants. The serene landscape includes distant views of the hills.
Cabin in Kangaroo Valley
4.96 out of 5 average rating, 443 reviews

Martha's Villa - panoramic, peaceful location

Please note, as Martha’s is advertised across multiple platforms and is able to be booked directly by searching for Martha’s Kangaroo Valley, your booking is not confirmed until you receive a booking confirmation from Airbnb. Treat yourself to an unforgettable, ambient escape with breathtaking views at all times of the day.

Top guest favorite
A spacious outdoor area is visible, featuring a grey wooden deck with a set of wooden chairs and a table. A pathway of square stones leads towards the entrance of the studio flat, surrounded by well-maintained grass. The studio's large glass doors invite natural light inside.
Guesthouse in Saint Georges Basin
4.94 out of 5 average rating, 742 reviews

Studio 22 at The Basin

Quiet residential area within minutes of St Georges Basin, Country Club and shopping centres. Short drive to beaches in Jervis Bay and the National Park. Lots of walking trails and activities. Most activities (stand up paddling, kayaking, surfing, bike riding, etc) are based at Huskisson which is a 10-15 minute drive away.

Top guest favorite
A serene landscape features a grassy pathway lined by trees, leading toward a soft horizon. A subtle rainbow arcs across the sky, offering a gentle splash of color against the backdrop of cloudy skies.
Guest suite in Berrima
4.95 out of 5 average rating, 389 reviews

Spacious Unit on Horse Property

Self-contained,attached,modern,spacious, 1 bedroom unit with kitchen on picturesque horse property. Dam, chicken coop, vegetable garden, use of inground pool and BBQ.10min to historic Berrima, 15 to Bowral & Mittagong. Close to Vineyards and Horse Trials. 2hrs to Canberra, 1.5hrs to Sydney Airport. 1.15hrs to SIEC.

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