Holiday rentals with a pool in Southern Highlands

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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 favourite
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, 132 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 favourite
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, 118 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

Superhost
The outdoor area features a heated swimming pool surrounded by a sun deck with lounge chairs. Umbrellas provide shade, while steps lead from the deck to the house. Panoramic ocean views are visible in the background, enhancing the space's serene atmosphere.
Home in Otford
4.92 out of 5 average rating, 153 reviews

"Seacliff" - Cliff Top Beach House

"Seacliff Otford" is just 60mins from Sydney CBD yet feels a million miles away. The house is on 2 acres, perched on the top of a hill, enjoying panoramic ocean views. Living areas face north enjoying all year sun . The lounge includes a log fire. There is a separate TV room, 4 double bedrooms, 2 bathrooms. The property includes a heated swimming pool (in summer) with large deck, lawned areas and a tennis court. STRICTLY 8 PEOPLE MAXIMUM, NO PARTIES, BUCKS WEEKENDS OR FUNCTIONS.

Top guest favourite
Tiny home in Callala Beach
4.97 out of 5 average rating, 117 reviews

Little Alby - Luxe Tiny Home

Little Alby is our luxe Tiny Home located in Callala Beach, the heart of Jervis Bay. Privately nestled amongst a stunning bush outlook and only steps to the beach. Watch the stars twinkle through the above bed skylight and let the sound of the waves lul you into a deep sleep. Our guests will indulge in luxurious linens and products from an array of premium brands including a special collaboration with Lurline Co, ensuring an exceptional and aesthetic experience.

Top guest favourite
An infinity pool is visible, featuring clear blue water that reflects the vibrant sky. The pool's edge seamlessly meets the glistening coastline, creating a serene atmosphere. Natural surroundings include trees and a tranquil shoreline.
Guest suite in Shellharbour
5 out of 5 average rating, 201 reviews

Wake up to the ocean at LegaSea

LegaSea is a self contained Guest House overlooking the historic Shellharbour boat harbour and coastline. Guests will feel as though they are levitating directly over the glistening waters of the calm harbour and can observe the activity of the nearby village from a comfortable, luxurious space. Village cafes and amenities are a short stroll away, and the beach or famous cowries surf break is at your doorstep. Find us on Instagram @Legasea_shellharbour

Top guest favourite
A modern swimming pool is surrounded by a glass barrier, offering views of the lush greenery and the lake in the distance. Comfortable lounge chairs are arranged around the pool deck, inviting relaxation. The serene atmosphere is enhanced by cloudy skies reflecting on the water's surface.
Flat in Albion Park Rail
4.96 out of 5 average rating, 100 reviews

Cabin situated beside lake and bike path

Minimum 2 night booking policy . Stay entire weekend request early check in or late check out, we will try to accomodate if possible Access the lake or bike path Swimming pool or Spa Great base for local attractions including kangaroo valley, Jamberoo action park, Berry and Shellharbour Walking distance to Albion park railway station Please understand this is a seperate cabin from the main house where we live it is very private

Guest favourite
A charming cabin is surrounded by greenery and colorful plants, set against a clear blue sky. The structure features a covered porch with large windows inviting natural light into the interior, creating a serene and peaceful environment.
Cabin in Kangaroo Valley
4.82 out of 5 average rating, 658 reviews

Breathe again, Cabin cuteness, entire cottage

This is a little piece of heaven, a moment for some tranquillity nestled within the Kangaroo Valley Golf Retreat located on the Golf Course. A short stroll to the pool. Volleyball. court all walking distance. 2 new tennis courts Walking distance to volleyball court, Giant chess set Badminton court & Swimming pool. Dive in. Quality inclusions. We are 4km from town. Single nite stays permitted.

Superhost
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, 121 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.

Guest favourite
A modern structure showcases large glass windows illuminating the interior against a dusky sky. The building is surrounded by lush greenery and is reflected in a tranquil pond, enhancing the serene and private environment.
Guest suite in Berry
4.97 out of 5 average rating, 154 reviews

Exclusive Mt Hay Retreat, Berry

Multi Award winning, family owned and operated Mt Hay Retreat is unique, private and ultra exclusive. A boutique escape that is simply second to none. With only a handful of individual residences, each luxury suite is filled with natural light and has been designed as your own private escape. Please note that we are unable to welcome guests aged under 18 years or pets of any kind.

Guest favourite
A light-filled window seat offers views of the lush green landscape and distant mountains. The outdoor area includes a pool and sun deck, visible beyond the expansive yard. The soft upholstery invites relaxation while enjoying the serene surroundings.
Cottage in Meroo Meadow
4.94 out of 5 average rating, 180 reviews

New Mercer cottage at Silvermist

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 favourite
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.
Guest house in Bowral
4.92 out of 5 average rating, 155 reviews

The Annexe at Beatrice Park, Bowral

Welcome to The Annexe at Beatrice Park Perfect for Couples or Solo Travelers 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.

Top guest favourite
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, 381 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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