Southern Highlands Vacation Rentals

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Vacation Rentals in Southern Highlands

TV, fireplace
Sauna Haus with Scandinavian design
10.0 out of 10, Exceptional, (30)
"Wonderful property, stayed short weekend. Perfect location."
The price is CA $226
CA $344 total
includes taxes & fees
May 21 - May 22
Sauna Haus with Scandinavian design
Interior
Greenview Bowral Southern Highlands
10.0 out of 10, Exceptional, (77)
"Amazing house. Perfect for our extended family. Only wish we could have stayed longe!"
Greenview Bowral Southern Highlands
Property grounds
Tiny house with acres of views.
10.0 out of 10, Exceptional, (39)
"This is our second visit here. It's a great place to stay for the weekend for two of us. The house is light and sunny, surprisingly spacious, clean, tidy and comfortable. It has everything we need for an overnight stay, and the peaceful country setting is beautiful. Hopefully we'll be back next year."
The price is CA $226
CA $288 total
includes taxes & fees
May 31 - Jun 1
Tiny house with acres of views.
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Fridge, microwave, oven, stovetop
Iona Park, Moss Vale
10.0 out of 10, Exceptional, (1)
"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
Outdoor pool, a heated pool
The ultimate luxury stay!
10.0 out of 10, Exceptional, (2)
"I have booked and stayed at many beautiful houses and hotels, so can say without a doubt that the calibre of this house cannot be beat. There was something for all ages, with no details missed. All the guest raved about how comfortable the beds were & how amazing it was that there were 20 of us there and yet we weren’t all on top of each other (there is just so much space). We will definitely book again!"
The ultimate luxury stay!
Terrace/patio
Martha's Villa - panoramic, peaceful location
10.0 out of 10, Exceptional, (43)
"What a fantastic getaway, David's little cabin is incredible, to be honest, the photos don't do it any justice, it's such a nice cosy little spot. Sit out on the deck, and crack a cold beer or enjoy a wine with amazing views. So close to Kangaroo valley town as well. Will be back."
The price is CA $235
CA $269 total
includes taxes & fees
May 29 - May 30
Martha's Villa - panoramic, peaceful location
Interior
Entire Ocean View Shell Cove Mansion - Sleeps 16 guests 5 minute from the beach!
10.0 out of 10, Exceptional, (11)
"Lovely house- very spacious everything we needed and more we didn’t use"
The price is CA $937
CA $1,535 total
includes taxes & fees
Jun 11 - Jun 12
Entire Ocean View Shell Cove Mansion - Sleeps 16 guests 5 minute from the beach!
Property grounds
A unique Southern Highlands experience
9.8 out of 10, Exceptional, (203)
"I really enjoyed my stay in this beautiful spot, the cottage had all I could ask for, in a lovely garden and the hosts were friendly and helpful. It is a little further out of town, I enjoyed the walk but some might prefer to travel by car. I was there for parkrun after all, which was only another 1km up the road in the Botanic gardens, so I was perfectly placed 🙂"
The price is CA $159
CA $186 total
includes taxes & fees
May 17 - May 18
A unique Southern Highlands experience
Property grounds
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
9.8 out of 10, Exceptional, (16)
"Daphne cottage was perfect, cozy with everything you could need for a weekend getaway. Walking distance to town and across the road from the Market Place which has beautiful meals."
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Terrace/patio
Crabapple Cottage -Lovely self contained cottage on Heritage property
9.8 out of 10, Exceptional, (146)
"Stylish & comfortable accommodation in easy walking distance of restaurant & shops"
Crabapple Cottage -Lovely self contained cottage on Heritage property
Beach nearby
Argo Serviced Apartments
3.5 star property
9.8 out of 10, Exceptional, (40)
"great place to stay"
The price is CA $191
CA $211 total
includes taxes & fees
May 20 - May 21
Argo Serviced Apartments
Outdoor pool, a heated pool
Luxury 5 B/R House with Pool, Lake & Beach
9.8 out of 10, Exceptional, (33)
"Great house for our little getaway. Host was very accommodating with any questions. Lots of room for our family. House was clean and tidy. Pool was great for the family. Just a note there a numerous stairs to get into property. Views were wonderful from numerous windows. We will return."
Luxury 5 B/R House with Pool, Lake & Beach
Exterior
Red Dog Retreat Cottages
9.8 out of 10, Exceptional, (88)
"Such a beautiful little cabin stay away from reality. Was just what we needed to reset ourselves. Absolutely loved it !"
Red Dog Retreat Cottages
Property grounds
Beach Retreat@Kiama BEACHFRONT with direct beach access
9.6 out of 10, Exceptional, (50)
"Really great spot and awesome value for money. Owners nice and friendly easy to deal with and helpful. Perhaps fridges could be colder and maybe an extra fan. Other than that beaut spot, close to great beach. Comfy and peaceful all round. Kids and I had a lovely time n"
Beach Retreat@Kiama BEACHFRONT with direct beach access
Pool
Lake David Luxury Lake House set on 40 acres - Sleeps 18
9.6 out of 10, Exceptional, (12)
"Would highly recommend for big groups"
Lake David Luxury Lake House set on 40 acres - Sleeps 18
Outdoor dining
Fairmont Cottage
9.6 out of 10, Exceptional, (264)
"Really enjoyed our stay, and felt welcomed as soon as we arrived to the warm and cosy cottage. It was only a short drive into Berry, and the location was very quiet and peaceful. Looking forward to coming back!"
Fairmont Cottage
On the beach, sun loungers, beach towels
Beachfront Escape. Just bring your beach towel! Winter Special late 3pm checkout
9.6 out of 10, Exceptional, (95)
"Fantastic location right on Jones beach. Facilities a little dated especially the kitchen and bathrooms. Also, no internal stairs between first and second floors. But you stay there just for the location."
Beachfront Escape. Just bring your beach towel! Winter Special late 3pm checkout
Fridge, microwave, oven, stovetop
Timbalah - a luxurious country retreat
9.4 out of 10, Exceptional, (91)
"We loved the character of the property and thoroughly enjoyed our stay on a very rainy weekend to celebrate several birthdays across a group of families. The layout of the living spaces was really comfortable and conducive to us all gathering together at one time or splitting into smaller groups to chat or play a game. There were a few leaks which wasn't totally surprising given the weather but none of them affected our stay. The fireplace was lovely, at times we found it a little challenging to...
Timbalah - a luxurious country retreat
Property grounds
Sherwood Park - A rural atmosphere in town / set on 2 acres
9.4 out of 10, Exceptional, (174)
"This house had everything we needed for a few old friends and their families to get together for a wonderful weekend in the country. The house was spotless, roomy, and provided great breakfasts, and the outdoor areas were huge and perfect for kids games."
Sherwood Park - A rural atmosphere in town / set on 2 acres
Microwave, coffee/tea maker, electric kettle, cookware/dishes/utensils
Adina Apartment Hotel Wollongong
4.5 star property
9.2 out of 10, Wonderful, (1806)
"The room was clean and comfortable to stay. Stuff members were friendly"
The price is CA $171
CA $188 total
includes taxes & fees
May 26 - May 27
Adina Apartment Hotel Wollongong
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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.

Southern Highlands Vacation Rental Travel Info

Vacation rentals
50
Popular accommodation
Southern Highlands private vacation homes
International airport
Sydney, NSW (SYD-Kingsford Smith Intl.)

Other types of properties in Southern Highlands you may be interested in

Courtyard Executive Family Room
Berrima Bakehouse Motel
3.5 star property
9.2 out of 10, Wonderful, (1000)
"Convenient location between ACT and Sydney. Self key less Check-in and out. Directions and signs not so clear if arriving at night."
The price is CA $145
CA $159 total
includes taxes & fees
May 19 - May 20
Berrima Bakehouse Motel
Indoor pool, outdoor pool
Park Proxi Gibraltar Bowral
3.5 star property
8.6 out of 10, Excellent, (914)
"Lovely spacious room with a very comfortable bed. Luxurious bathroom."
The price is CA $190
CA $209 total
includes taxes & fees
May 19 - May 20
Park Proxi Gibraltar Bowral
Reception hall
Berida Hotel
4.0 star property
8.4 out of 10, Very good, (1000)
"Great service and location. Dining and drinks options were great."
The price is CA $190
CA $209 total
includes taxes & fees
May 28 - May 29
Berida Hotel
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.

Everything you need to know about Southern Highlands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Highlands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Highlands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southern Highlands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Highlands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southern Highlands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southern Highlands vacation rentals we have selected for you start as low as CA $136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southern Highlands rentals

At Expedia, we put the best Southern Highlands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southern Highlands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Highlands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Highlands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews of Southern Highlands properties
Expedia verified reviews

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

5/5 Excellent
Luxury in Bowral
"Lovely spacious room with a very comfortable bed. Luxurious bathroom."
A verified traveller stayed at Park Proxi Gibraltar Bowral
Posted 2 days ago
Park Proxi Gibraltar Bowral