Southern Highlands Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Southern Highlands Vacation Homes

Kendall’s Beach Cottage
Beach nearby

Kendall’s Beach Cottage

10.0 out of 10, Exceptional, (90)
"Great place very close to the beach."
Kendall’s Beach Cottage
Cosy country stay in beautiful Berrima.
Property grounds

Cosy country stay in beautiful Berrima.

10.0 out of 10, Exceptional, (12)
"Fantastic place. Super nice, very cool country home in Berrima. Beautifully decorated great fire, bbq, deck. Makes for a nice weekend away. "
Cosy country stay in beautiful Berrima.
Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!
Smart TV, fireplace, computer monitors

Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!

9.8 out of 10, Exceptional, (6)
"We loved our stay at the Jean House. The house is very spacious and the games room is amazing. Host was very responsive."
The price is CA $670
CA $709 total
includes taxes & fees
Aug 13 - Aug 14
Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!
Secret Garden – Stay 3, Pay 2!
Dining

Secret Garden – Stay 3, Pay 2!

The price is CA $2,428
CA $2,428 total
includes taxes & fees
Aug 13 - Aug 14
Secret Garden – Stay 3, Pay 2!
Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST
Fridge, microwave, oven, stovetop

Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST

8.6 out of 10, Excellent, (107)
"We had a wonderful stay in this beautiful home! Very central to town centre walking distance to everything! Would definitely recommend this place!"
Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST
The Boathouse/ Luxury Home/4mins walk Marina/Shops
Interior

The Boathouse/ Luxury Home/4mins walk Marina/Shops

10.0 out of 10, Exceptional, (24)
"A lovely property, everything spot on ! "
The Boathouse/ Luxury Home/4mins walk Marina/Shops
Iona Park, Moss Vale, Southern Highlands
Fridge, microwave, oven, stovetop

Iona Park, Moss Vale, Southern Highlands

9.0 out of 10, Wonderful, (2)
"We had a large group of friends staying at Iona Park for a reunion and we were all absolutely blown away. From the moment you arrive, the facilities are jaw dropping. Both the inside, especially the pool room and library, and outside (double tennis court!) were stunning. The kitchen was well stocked and plenty big enough to accommodate all of us. The check-in process was very smooth and the hosts were a pleasure to deal with. I can’t recommend this stay highly enough!"
Iona Park, Moss Vale, Southern Highlands
Luxury Heritage Cottage In The Heart Of Town
Outdoor dining

Luxury Heritage Cottage In The Heart Of Town

10.0 out of 10, Exceptional, (170)
"Perfect location and beautiful home. "
Luxury Heritage Cottage In The Heart Of Town
Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit
Beach nearby

Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit

8.6 out of 10, Excellent, (27)
"Good property close to the beach and all the sights of the region."
The price is CA $557
CA $557 total
includes taxes & fees
Aug 13 - Aug 14
Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit
Beautifully renovated Mountain cottage with Ocean view
Terrace/patio

Beautifully renovated Mountain cottage with Ocean view

10.0 out of 10, Exceptional, (105)
"Great stay"
Beautifully renovated Mountain cottage with Ocean view
Twin Peaks - Kangaroo Valley
Terrace/patio

Twin Peaks - Kangaroo Valley

10.0 out of 10, Exceptional, (5)
"Convenient location to village amenities and surrounding activities. Very clean and comfortable with excellent decor and furnishings. Perfect for weekend getaway."
The price is CA $491
CA $491 total
includes taxes & fees
Aug 13 - Aug 14
Twin Peaks - Kangaroo Valley
The South Coasts Ultimate Luxury Beachfront - NEW LISTING
Terrace/patio

The South Coasts Ultimate Luxury Beachfront - NEW LISTING

10.0 out of 10, Exceptional, (33)
"Excellent premium property with the best location on 7 mile beach"
The South Coasts Ultimate Luxury Beachfront - NEW LISTING
Beautiful Large Country Home in the Perfect Location with tennis court & theatre
Property grounds

Beautiful Large Country Home in the Perfect Location with tennis court & theatre

10.0 out of 10, Exceptional, (20)
"Very nice accommodation, great hosts. Very easy to communicate with. We had a great weekend"
Beautiful Large Country Home in the Perfect Location with tennis court & theatre
Razorback Dream Farmhouse: 10BR, Space & Serenity
Outdoor pool

Razorback Dream Farmhouse: 10BR, Space & Serenity

8.2 out of 10, Very good, (38)
"Good for large group"
Razorback Dream Farmhouse: 10BR, Space & Serenity
Greenview Bowral Southern Highlands
Interior

Greenview Bowral Southern Highlands

10.0 out of 10, Exceptional, (91)
"The entire process from booking to the actual stay was seamless. There was plenty of room for our 20 guests, the hosts have thought of everything and the property manager was excellent. It made our wedding weekend fabulous!"
Greenview Bowral Southern Highlands
Timbalah - a luxurious country retreat
Fridge, microwave, oven, stovetop

Timbalah - a luxurious country retreat

9.2 out of 10, Wonderful, (112)
"Good communication and flexibility from hosts to accomodate our group. "
Timbalah - a luxurious country retreat
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Interior

Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima

9.6 out of 10, Exceptional, (64)
"Cottage was absolutely great for what we needed to stay two nights in BerrimaCottage very cleanBackyard to the river was lovely,it even had a pond for ducks The Hosts were absolutely so helpful and very friendly "
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Beachfront House with direct access to the Beach. Just bring your beach towel!
On the beach, sun loungers, beach towels

Beachfront House with direct access to the Beach. Just bring your beach towel!

9.6 out of 10, Exceptional, (110)
"Location & view of the beach was perfect.Ten of us stayed & we were all very comfortable We had a fun few days together. Amanda was a great host- she was very easy to communicate with."
Beachfront House with direct access to the Beach. Just bring your beach towel!
Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.
Interior

Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.

10.0 out of 10, Exceptional, (1)
"Beautiful, clean and practical layout."
Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.
Belle in Bowral - walk to town
Outdoor dining

Belle in Bowral - walk to town

9.8 out of 10, Exceptional, (55)
"Great location. Perfect accommodation for a Centennial Vineyard concert short stay."
The price is CA $241
CA $375 total
includes taxes & fees
Aug 18 - Aug 19
Belle in Bowral - walk to town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Highlands Hotel Reviews

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

10/10 Excellent
"Quality accommodation. Very spacious room overlooking lake. Quiet, clean and very comfortable. Ample parking out the front and extremely friendly and helpful staff. Great spot to relax and recuperate. Whole family stayed in three rooms and check in process was seamless. Recommhighly. "
Alan 1-night trip
Posted 16 hours ago
Park Proxi Gibraltar Bowral