Holiday 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 favourite

Apartment in Dapto

4.97 out of 5 average rating, 206 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

17 – 24 June

$1,279 AUD total

Guest favourite

Guest suite in Huskisson

4.97 out of 5 average rating, 114 reviews

Boat Builder's Garden Studio with pool.

The north facing studio accommodation is separate to the main house and contains a light filled bedroom, large bathroom with shower and toilet, a breakfast area with fridge, microwave, toaster, coffee and tea making facilities. Perfect accommodation for a couple who appreciate a tastefully decorated, private and peaceful space. Enjoy the swimming pool and garden setting. Located a leisurely five minute walk from Huskisson town centre and within easy reach to all that Jervis Bay has to offer.

12 – 19 June

$1,090 AUD total

Guest favourite

Guesthouse in Bowral

4.9 out of 5 average rating, 121 reviews

Beatrice Park - The Annexe

THE ANNEXE is perfect for couples or single travellers. ASK ABOUT OUR LAST MINUTE RATES & WELCOME PACK In the HERITAGE LISTED GARDENS of BEATRICE PARK but separate enough for your privacy to be guaranteed. A perfect RETREAT for a week end or a week away: ANTIQUES GALLERIES FOOD & VINEYARDS BOOKSHOPS FESTIVALS - MUSIC - SHAKESPEARE GOLF BUSHWALKS FISHING HORSERIDING CYCLING POLO MARKETS BONG BONG RACES We cater for people on business in the HIGHLANDS for stays longer than 2 nights.

6 – 13 Apr

$1,416 AUD total

Guest favourite

Cottage in Meroo Meadow

4.96 out of 5 average rating, 141 reviews

New Atlas at Silvermist South Coast

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 on the beautiful South Coast of N.S.W. The cottages can be booked individually sleeping up to 4 guests per cottage, or as a multi cottage booking. The neighbouring cottage is called Mercer at Silvermist, on 25 acres of privately owned land.

14 – 21 Jan

$2,852 AUD total

Guest favourite

Tiny home in Burradoo

4.9 out of 5 average rating, 147 reviews

Highlands getaway

A completely self contained cottage surrounded by beautiful gardens. There is a pool on the property which guests may use. The cottage is in a beautiful leafy suburb of Bowral containing interesting shops , walks, cycling tracks. There are numerous places of interest in the surrounding towns and villages . There is also a fully self contained 2 bedroom aprt(1 queen bed and 1 single bed) on the property . See listing Luxurious Hideaway in BOWRAL airbnb.com./rooms/17128739

2 – 9 May

$1,341 AUD total

Guest favourite

Guesthouse in Kiama Heights

5.0 out of 5 average rating, 119 reviews

Ocean Views Private Luxury Escape Waterfront Kiama

Experience the ultimate coastal getaway at this stunning couple's retreat & enjoy breathtaking views of Love’s Bay and the Pacific Ocean from every room. Relax by the lap pool, soak up the sun on your private balcony, or cozy up by the outdoor firepit. Watch the awe-inspiring spectacle of whales migrating along the coast, or explore the nearby beach and town. The apartment offers a stylish and comfortable space for couples seeking a romantic escape or a memorable holiday.

21 – 28 Feb

$3,667 AUD total

Guest favourite

Guest suite in Gerringong

4.94 out of 5 average rating, 181 reviews

"The Docks" Drift down, relax, explore, refresh

This Private luxury guest facility is spacious and private from the rest of the house. The space overlooks a recently landscaped yard and resort style pool. The pool is a shared space with the host's, however guest's are respected and given privacy where possible. Situated close to Werri Beach and Boat harbour, salt water pool and only 6min walk to cafes and restaurants. Enjoy beautiful views from the deck out to Boat harbour headland and out to the pacific ocean.

11 – 18 May

$1,855 AUD total

Guest favourite

Cabin in Kangaroo Valley

4.8 out of 5 average rating, 498 reviews

Breathe again, Cabin cuteness, entire cottage

This is a little piece of heaven a moment for some tranquillity and enough to keep the children busy with the pool golf & volleyball. all walking distance in the front yard. Shower 2 new tennis courts Walking distance to volleyball court, Giant chess set Badminton court & pool. Quality inclusions. We are 4km from town. Single nite stays please bring own linen, we will supply all towels doonas, blankets, bath mat flannels etc. Queen bed.

13 – 20 June

$1,311 AUD total

Guest favourite

Barn in East Kangaloon

4.98 out of 5 average rating, 121 reviews

The Sheds at Wombat Hollow Accommodation

The Games Shed is one luxurious open plan space. Sleeping, eating, cooking and relaxing all revolve around the open fireplace. The Games Shed accommodates 6 people in 1 Queen Bed and 4 Single beds. As an add-on to The Games Shed, 2 - 4 people can sleep in 2 double beds in the warm and cosy Arena Hut. The Arena Hut is a detached cottage with no bathroom facilities within a easy walking distance to The Games Shed, think LUXE GLAMPING!

1 – 8 May

$3,324 AUD total

Guest favourite

Home in Colo Vale

4.89 out of 5 average rating, 153 reviews

The Highland House

This stunning Highland home is a beautiful combination of stone, glass and timber. We are one of the few Southern Highlands homes with a pool. The Highlands House uses design features and classic styling with the large group in mind. We have an oversized entertaining room, 3 slow combustion wood heaters and reverse-cycle air conditioning. The decks give rural views over glorious gardens, dam and swimming pool, spa and sauna.

11 – 18 Jan

$12,394 AUD total

Guest favourite

Cabin in Kangaroo Valley

4.96 out of 5 average rating, 325 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.

22 – 29 Oct

$1,691 AUD total

Guest favourite

Guesthouse in Saint Georges Basin

4.94 out of 5 average rating, 517 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.

11 – 18 Dec

$1,039 AUD total