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

Apartment in Dapto

4.97 out of 5 average rating, 207 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

Oct 6 – 13

R2,520 ZAR per night

Guest favorite

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.

Sep 11 – 18

R2,261 ZAR per night

Guest favorite

Cottage in Meroo Meadow

4.96 out of 5 average rating, 145 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.

Aug 31 – Sep 7

R3,987 ZAR per night

Guest favorite

Tiny home in Burradoo

4.91 out of 5 average rating, 150 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

Oct 26 – Nov 2

R2,280 ZAR per night

Guest favorite

Guesthouse in Kiama Heights

5.0 out of 5 average rating, 121 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.

Sep 7 – 14

R6,165 ZAR per night

Guest favorite

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.

Jul 4 – 11

R3,150 ZAR per night

Guest favorite

Guesthouse in Berry

4.92 out of 5 average rating, 295 reviews

Windsor Cottage

Cosy, country cottage style two bedroom cottage within easy 1km walk to Berry town centre. Would suit a couple with two children or two couples. A great base for accessing all the area has to offer. Recently refurbished with new carpet, paint and kitchenette. Access to pool and outdoor entertaining area. Friendly local hosts who are happy to recommend attractions including beaches, wineries, restaurants and the amazing new Boongaree Rotary Nature Park.

Mar 7 – 14

R2,668 ZAR per night

Guest favorite

Cabin in Kangaroo Valley

4.8 out of 5 average rating, 499 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.

Jun 25 – Jul 2

R2,409 ZAR per night

Guest favorite

Barn in East Kangaloon

4.98 out of 5 average rating, 122 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!

Jul 10 – 17

R5,801 ZAR per night

Guest favorite

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.

Apr 20 – 27

R20,417 ZAR per night

Guest favorite

Cabin in Kangaroo Valley

4.96 out of 5 average rating, 326 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.

Sep 20 – 27

R2,951 ZAR per night

Guest favorite

Guesthouse in Saint Georges Basin

4.94 out of 5 average rating, 521 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.

Dec 23 – 30

R1,813 ZAR per night