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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cabin in Kangaroo Valley

4.94 out of 5 average rating, 210 reviews

Rainbow Reach country cabin

Gorgeous two bedroom, two bathroom cabin on the golf course at Kangaroo Valley. Just 2 hours from Sydney and a million miles from care! Lots of windows flood the cabin with light, and the white walls, comfy beds, and fantastic sofa give a relaxed country vibe. Timber decks front and back and a level lawn give you plenty of places to relax. And we now have internet! Which most golf course cabins are missing. So you can work from the cabin if you need to ... or switch off and enjoy the serenity.

Guest favorite

Cabin in Kangaroo Valley

4.97 out of 5 average rating, 113 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.

Guest favorite

Home in Kangaroo Valley

4.98 out of 5 average rating, 116 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

Home in Kangaroo Valley

4.87 out of 5 average rating, 338 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.

Guest favorite

Cottage in Meroo Meadow

4.94 out of 5 average rating, 161 reviews

New Mercer cottage at Silvermist

Silvermist offers 3 private, separate and luxuriously appointed cabins nestled into 25 green acres. With spectacular mountain views, lush green meadows & gorgeous interiors, they're located minutes drive from the town of Berry, and the beaches of the beautiful South Coast of N.S.W. The cabins can be booked individually sleeping up to 4 guests per cottage, or as a multi cottage booking. The neighbouring cottage is called Atlas at Silvermist, on 25 acres of privately owned land.

Guest favorite

Home in Kangaroo Valley

4.93 out of 5 average rating, 287 reviews

SkyView Villa - WOW Views & Comfort

Set on 150 acres of manicured rolling green hills, SkyView enjoys arguably the best views in a country resort with sweeping views over lakes, glades and the lush green golf course. Ideal for families and couples alike, beautifully appointed and comfortable. Skyview Villa has the Aspire range of mattresses from Sealy Posturepedic, thus ensuring guests the best possible night's sleep. Skyview villa offers free WiFi, plus Netflix & Austar via two 65 inch smart TV's.

Superhost

Home in Burradoo

4.89 out of 5 average rating, 297 reviews

Arafel Park - Luxury Bowral Estate

Arafel Park is a stunningly renovated original Southern Highlands 1930's estate. Proudly sitting on 2 acres of cold climate gardens, the property features a main residence and a separate servants cottage. The main house has 4 bedrooms (2 of them are adjoining) that holds 1 King bed and 3 queens. The cottage has 2 bedrooms with one King and one Queen bed. The lounge room of cottage has a daybed and a trundle or porta-cot that can be setup on request.

Superhost

Farm stay in Penrose

4.87 out of 5 average rating, 117 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

Home in Bundanoon

4.89 out of 5 average rating, 132 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.

Top guest favorite

Guesthouse in Bowral

4.92 out of 5 average rating, 146 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.

Guest favorite

Cabin in Kangaroo Valley

4.96 out of 5 average rating, 406 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.

Guest favorite

Guest suite in Berrima

4.95 out of 5 average rating, 368 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.