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Vacation rentals with a pool in Southern Highlands

Find and book unique homes with a pool on Airbnb

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Popular amenities for Southern Highlands rentals with a pool

House rentals with a pool

Guest favorite
Home in Kangaroo Valley
4.95 out of 5 average rating, 80 reviews

Mike's - A luxurious cabin surrounded by nature

CharlotteRating, 5 stars3 days ago
Michael’s place was truly amazing. Beautiful locations, very private which is exactly what my boyfriend and I wanted. This was by far the most stocked up AirBnB I’ve ever stayed at; the kitchen, the hot tub, gorgeous comfy beds, games, tv with all the apps; I could go on and on. Michael is a great host with clear instructions, fast communication and lots of suggestions. If you’re thinking of booking, just do it!! Kangaroo Valley is the perfect getaway and this place is the perfect little spot to stay. There’s quite a bit to do in the valley itself and from Michael’s it’s very easy to get to other towns. We will definitely be back!
Guest favorite
Home in Moss Vale
4.91 out of 5 average rating, 22 reviews

Sutton House Southern Highlands

SebastianRating, 5 stars1 month ago
We had a wonderful time at Pip’s property. Conveniently located less than 5mins from Miss Vale and 15mins from Bowral, it was a perfect spot to explore the southern highlands. The property was beautiful and pristine, just like the photos. The house was cosy and welcoming and the grounds were lovely to explore. The kids loved running around in the big back yard and exploring the pond, and love the fact the neighbors were just two cows. The swimming pool was clean and modern. The kids didn’t want to leave and we’ll definitely be back. Thanks for having us Pip!
Guest favorite
Home in Kiama Downs
4.93 out of 5 average rating, 142 reviews

Jones Beach Retreat - Pool, close to beach & cafes

JanetteRating, 5 stars6 days ago
Such a great spot, we kayacked on the Minnamurra River and really enjoyed the close vicinity of the beach and coffee shops. We are already planning to return. Thanks Jenna and Joel also for the welcome pack of wine and nibbles.
Top guest favorite
Home in Woodlands
5 out of 5 average rating, 27 reviews

Cuttaway Cottage

AnastasiaRating, 5 stars4 days ago
Incredible stay at the most idealic home. It was cosy, well thought out and we could tell the hosts really cared about every detail. It was warm, welcoming, spacious, beautiful rooms, amazing fireplace and even underfloor heating. The kitchen was great too. Wish we stayed longer! The best surprise was waking up in the morning and seeing the horses, ponies and donkeys outside the windows. It was a dream. We stayed with my two little ones and my parents - two great bathrooms and lots of space for everyone. The hosts were super communicative and the best hosts I’ve ever met taking the time to show my kids around the animals and farm. Just perfect, can’t wait to come back! Also only 10 minutes from Bowral.
Guest favorite
Home in Wollumboola
4.93 out of 5 average rating, 120 reviews

ALINDA FARM HOUSE! From farm to beach in 5 minutes

HayleeRating, 5 stars1 month ago
Perfect property for our group of friends and kids getaway. We weren’t sure what the weather was going to be like but the house caters for rain hail or shine. The two living areas worked well for kids too. 5 min drive from the beach and plenty to see in the area. Thanks for having us!
Top guest favorite
Home in Upper Kangaroo River
5 out of 5 average rating, 64 reviews

3 BR Newly Renovated Private Farmhouse

LisaRating, 5 stars1 month ago
Photos cannot do the stunning views justice, we arrived ready to decompress from the city and this was the perfect spot. We enjoyed the cosy and clean accommodation, log fire, swam in the pool, read books, cooked and took a couple of walks. Wonderful hosts provided fresh bread, home made jam and eggs. Everything you’ll need, a delightful spot to unplug and soak up nature.
Top guest favorite
Home in Berry
4.97 out of 5 average rating, 33 reviews

Hazel House Berry

SusanRating, 5 stars1 month ago
Gorgeous house in a fabulous location . Natalie was an amazing host - the house was Immaculately presented and we were welcomed with French champagne! We will definitely rebook !
Top guest favorite
Home in Shoalhaven Heads
4.97 out of 5 average rating, 115 reviews

The Grove - Luxury Stays

MelanieRating, 5 stars1 month ago
This was the perfect Airbnb for a mini break with our group of friends and kids. The house has everything you could ever think of, toys, books, linen, towels, cooking utensils. There is a short walk to the beach from the property and we often encountered horses on the way, just lovely. The outdoor area with the bbq and fire pit was used for almost every meal and was a great spot for us all to hang out. It was a truly memorable stay and we already look forward to the next stay!

Condo rentals with a pool

Guest favorite
Condo in Wollongong
4.89 out of 5 average rating, 155 reviews

The Pacific View Studio Penthouse Suite

DaanikaRating, 5 stars3 weeks ago
Wonderful location and view. Well worth the money!
Condo in Rockdale
4.66 out of 5 average rating, 115 reviews

LARGE APARTMENT CLOSE TO AIRPORT & HOSPITALS

EricRating, 5 stars5 months ago
Very convenient location
Condo in Port Kembla
4.69 out of 5 average rating, 13 reviews

Absolute Beach front accommodation.

KevinRating, 5 stars1 week ago
Great Beach side location in a quiet and safe neighborhood. Lee provided a mini fridge full of snacks and drinks which served as breakfast. it's a shame we only stayed one night, his place would've been perfect for a multi night getaway from the busy Sydney life.
Condo in Bowral
4.8 out of 5 average rating, 71 reviews

Golf View Villa Bowral

RobertRating, 5 stars2 weeks ago
Perfect location. Close to everything Bowral has to offer. Comfortable villa with everything you need. A real suntrap during the day. Ideal 3-night stay
Condo in Wollongong
4.72 out of 5 average rating, 151 reviews

"Orana" to The 'Gong

SamanthaRating, 5 stars2 weeks ago
Fabulous property in a great location - surrounded by cafes, restaurants and the onsite parking is a great bonus for when wanting to drive beyond walkable surrounds. The positive experience with the host contributed to our overall enjoyment of the stay. I can happily say she lives up the reputation of previous reviews!! Highly recommend.
Guest favorite
Condo in Thirroul
4.98 out of 5 average rating, 46 reviews

Coastal Rainforest Retreat

SamanthaRating, 5 stars1 month ago
The Coastal Rainforest Retreat was the perfect stay, and just what we were looking for. A quick drive to restaurants and beaches. Would highly recommend!!

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