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

Home in Bundeena

4.87 out of 5 average rating, 188 reviews

Bundeena Base Art House Sea View Solar Heated Pool

With fabulous views, overlooking the sea, Bundeena Base offers self-contained accommodation for up to 8 people. With your own private in-ground solar heated pool and 3 beaches 500 meters away, you're spoilt for choice. 3 bedrooms, lounge dining, well equipped kitchen, generous 3-way bathroom suite & outdoor covered terrace, perfect for dining or relaxing with a cool drink of your choice Prices based on 6 guests $35 per additional guest Filtered water Chlorine free pool 100% cotton bed linen

Superhost

Home in Nowra

4.67 out of 5 average rating, 15 reviews

Blue Horizon House With Private Pool. Pet Friendly

Welcome to Blue Horizon - A Lush Oasis with Pool for Family Fun Located in a tranquil spot in Nowra, South Coast, yet just about 10 minutes' drive from stunning beaches, it offers a peaceful family retreat. This property, with its splendid pool, comfortably accommodates up to 8 guests. Perfect for families or friends, it's also pet-friendly with 24-hour off-leash access at nearby Ratcliff Park. Enjoy the convenience of being minutes away from local shopping while staying away from the bustle

Guest favourite

Home in Coolangatta

4.95 out of 5 average rating, 147 reviews

Vineyard Vista

Nestled between two of the Shoalhavens best wineries,Vineyard Vista ticks all the boxes. Located on a quiet and private road,our three bedroom house is only minutes to Shoalhaven Heads beach,the local golf course or the Shoalhaven River if you fancy throwing in a line. The vibrant hub of Berry is only a 10 minute drive,where you can enjoy the streetside cafes,or just wander through the many homeware and antique shops. Relax with your own BBQ and al fresco dining,or just hang by the shared pool.

Top Guest favourite

Guesthouse in Bulli

4.98 out of 5 average rating, 248 reviews

Studio Retreat & Pool close to Beach min 1 night

Studio Retreat offers comfort, privacy, air conditioning and is self-contained. It has a full kitchen and bathroom catering for 2 guests. The property is minutes' walk from the beach, bike track and cafes. The railway station, restaurants, pub and brewery are only a 10 to 15 minutes stroll away. You will enjoy use of the pool and BBQ area also Netflex Note this is a 1 room studio with separate bathroom Only 2 guest per stay - Check in 2 pm - Checkout 10am - No Pets - No Events or Parties

Top Guest favourite

Home in Lake Illawarra

5 out of 5 average rating, 148 reviews

BEACH-FRONT! Luxury House with Pool & SPA

EARLY CHECK-IN (11am)+ LATE CHECK-OUT (2pm) Make the most of your stay here... Architecturally designed, custom-built, luxury home. Choice of entertaining areas, water views, directly opposite the beach! Seamless indoor/ outdoor entertaining areas, two outdoor kitchens, & full house SONOS sound system. Although a Summer beach holiday may seem ideal, Winter time is also great time to holiday here! There is nothing better than a hot spa, or relaxing by the fireplace on a Cold Winters day.

Guest favourite

Apartment in Dapto

4.95 out of 5 average rating, 242 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

Guest favourite

Cabin in Kangaroo Valley

4.82 out of 5 average rating, 593 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 please bring own linen, we will supply all towels doonas, blankets, bath mat flannels etc. Queen bed.

Guest favourite

Apartment in Kiama Downs

4.9 out of 5 average rating, 116 reviews

Kiama Seaside Escape 1 Jones Beach

Kiama Seaside Escape 1 at Jones Beach Location , location ! First Floor Duplex at Jones Beach with Pool and Wifi This stylish designer apartment is perfectly located across the road from Jones Beach with IGA supermarket, local shops and cafes around the corner. There is no need to leave this secret haven. The first floor apartment is a perfect for a family holiday, a girls weekend away, golfing with friends at the nearby Kiama Golf Club or a kayak adventure at Minnamurra River.

Top Guest favourite

Tiny home in Burradoo

4.91 out of 5 average rating, 164 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

Guest favourite

Guesthouse in Berry

4.93 out of 5 average rating, 338 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.

Guest favourite

Home in Erowal Bay

4.92 out of 5 average rating, 180 reviews

TREETOPS 4 TWO

Note: Full refund issued due to Covid related restrictions " TREETOPS 4 TWO " is a modern luxury place for two, the home includes an amazing upstairs master bedroom with spa/hot tub over looking the trees through to the water, private plunge pool for summer, double sided gas log fire for those colder romantic winter nights & games room for those wanting to play pool listen to music on the juke box or watch the large wall mounted tv

Guest favourite

Home in Bundanoon

4.89 out of 5 average rating, 125 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.