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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Guest favorite

Cabin in Kangaroo Valley

4.97 out of 5 average rating, 117 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

Apartment in Dapto

4.96 out of 5 average rating, 252 reviews

2 BR apartment with billiards room, pool & spa

A quiet relaxing getaway close to Wollongong, ocean, lake & mountains. Inside: Almost an entire house fitted with quality inclusions (NB: Apartment attached to house in which I live). There are 2 bedrooms, a sitting & a billiards room, laundry, full kitchen & bathroom (AC, cable TV, highspeed internet) Outside: Enjoy dining next to your private spa on the veranda or by the pool. Close to transport, shops, lake, beaches, National Parks, Jambaroo Action Park, Kiama Blowhole, Nan Tien Temple

Top guest favorite

Cottage in Kiama

4.95 out of 5 average rating, 144 reviews

Kiama Farmhouse

Kiama Farmhouse is a beautiful original weather board cottage that has been lovingly restored and fitted with all the comforts of a modern home . It is surrounded by lush rolling dairy pastures yet is only four minutes drive to Kiama township and the stunning beaches of Kiama . The ambient surrounds will relax and delight you in this home away from home.We are a pet friendly home with a fully fenced garden which allows your pets to be safe and happy here. Complete with a stunning outdoor pool

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 Otford

4.92 out of 5 average rating, 151 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.

Guest favorite

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

Home in Kangaroo Valley

4.93 out of 5 average rating, 290 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.

Guest favorite

Home in Burradoo

4.89 out of 5 average rating, 303 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, 119 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

4.9 out of 5 average rating, 134 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

Cottage in Meroo Meadow

4.94 out of 5 average rating, 165 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 favorite

Guesthouse in Bowral

4.92 out of 5 average rating, 150 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.