Photo by Cathy Fuentes
Holiday rentals near Castlereagh Street
We found 3,309 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Castlereagh Street that provide the perfect home base for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Castlereagh Street
Showing deals for:14 Nov - 21 Nov
Image gallery for Pet Friendly Modern Apartment in Rose Bay near water
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Pet Friendly Modern Apartment in Rose Bay near water
Sydney, NSW
8% off
Price is AU$2,121
AU$2,121
AU$303 per night
includes taxes & fees
Image gallery for Manly Sunshine Cottage - quiet family retreat
1010 out of 10 rating
Exceptional
(58 reviews)
Manly Sunshine Cottage - quiet family retreat
Sydney, NSW
11% off
Price is AU$2,061
AU$2,061
AU$294 per night
includes taxes & fees
Image gallery for Balmoral Escape - footsteps from beach
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Balmoral Escape - footsteps from beach
Sydney, NSW
9% off
Price is AU$2,721
AU$2,721
AU$389 per night
includes taxes & fees
Image gallery for Cosy Hidden Gem with History. Next to Park. Pet Friendly.
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cosy Hidden Gem with History. Next to Park. Pet Friendly.
Sydney, NSW
8% off
Price is AU$1,411
AU$1,411
AU$202 per night
includes taxes & fees
Image gallery for Leafy and Tranquil Inner West Studio Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Leafy and Tranquil Inner West Studio Apartment
Sydney, NSW
5% off
Price is AU$1,592
AU$1,592
AU$227 per night
includes taxes & fees
Image gallery for 4 bedroom home with bay views
9.69.6 out of 10 rating
Exceptional
(5 reviews)
4 bedroom home with bay views
Sydney, NSW
8% off
Price is AU$3,385
AU$3,385
AU$484 per night
includes taxes & fees
Image gallery for Beautiful Beach-side cottage with lap pool in North Maroubra close to Coogee
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Beautiful Beach-side cottage with lap pool in North Maroubra close to Coogee
Sydney, NSW
9% off
Price is AU$2,366
AU$2,366
AU$338 per night
includes taxes & fees
Image gallery for Entire 4 Bedroom Paddington Terrace
9.09.0 out of 10 rating
Wonderful
(26 reviews)
Entire 4 Bedroom Paddington Terrace
Sydney, NSW
9% off
Price is AU$4,252
AU$4,252
AU$607 per night
includes taxes & fees
Image gallery for Lovely Apartment in Darlinghurst
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Lovely Apartment in Darlinghurst
Sydney, New South Wales
5% off
Price is AU$2,196
AU$2,196
AU$314 per night
includes taxes & fees
Image gallery for Double Bay three-bedroom apartment with pool
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Double Bay three-bedroom apartment with pool
Sydney, NSW
8% off
Price is AU$3,392
AU$3,392
AU$485 per night
includes taxes & fees
Image gallery for 1 BR BEACHSIDE RETREAT WITH LAP POOL - close to Coogee Beach
9.29.2 out of 10 rating
Wonderful
(19 reviews)
1 BR BEACHSIDE RETREAT WITH LAP POOL - close to Coogee Beach
Sydney, NSW
10% off
Price is AU$1,659
AU$1,659
AU$237 per night
includes taxes & fees
Image gallery for Balmoral Salt Apartment 150m to Balmoral Beach
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Balmoral Salt Apartment 150m to Balmoral Beach
Sydney, NSW
9% off
Price is AU$1,189
AU$1,189
AU$170 per night
includes taxes & fees
Image gallery for STUNNING SYDNEY HOME 9
9.49.4 out of 10 rating
Exceptional
(12 reviews)
STUNNING SYDNEY HOME 9
Sydney, New South Wales
5% off
Price is AU$2,899
AU$2,899
AU$414 per night
includes taxes & fees
Image gallery for Perfect Laneway Terrace, Surry Hills
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Perfect Laneway Terrace, Surry Hills
Sydney, New South Wales
5% off
Price is AU$3,321
AU$3,321
AU$474 per night
includes taxes & fees
Image gallery for Bondi Beach Premium 2 bed Apt | Views | Parking
1010 out of 10 rating
Exceptional
(6 reviews)
Bondi Beach Premium 2 bed Apt | Views | Parking
Sydney, New South Wales
6% off
Price is AU$4,598
AU$4,598
AU$657 per night
includes taxes & fees
Image gallery for The Tardis2 - Huge Leafy Balcony BBQ
1010 out of 10 rating
Exceptional
(24 reviews)
The Tardis2 - Huge Leafy Balcony BBQ
Sydney, NSW
9% off
Price is AU$1,272
AU$1,272
AU$182 per night
includes taxes & fees
Image gallery for Manly oasis - wonderful street in manly - perfect place to stay, free parking
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Manly oasis - wonderful street in manly - perfect place to stay, free parking
Sydney, NSW
9% off
Price is AU$1,831
AU$1,831
AU$262 per night
includes taxes & fees
Image gallery for SYDNEY Stunning Home 2
9.29.2 out of 10 rating
Wonderful
(15 reviews)
SYDNEY Stunning Home 2
Sydney, New South Wales
5% off
Price is AU$2,725
AU$2,725
AU$389 per night
includes taxes & fees
Image gallery for ULTIMATE BONDI LIVING
8.08.0 out of 10 rating
Very good
(8 reviews)
ULTIMATE BONDI LIVING
Sydney, New South Wales
5% off
Price is AU$2,277
AU$2,277
AU$325 per night
includes taxes & fees
Image gallery for No 96 Holiday House Kurnell
1010 out of 10 rating
Exceptional
(42 reviews)
No 96 Holiday House Kurnell
Sydney, NSW
9% off
Price is AU$2,453
AU$2,453
AU$350 per night
includes taxes & fees
Image gallery for Linley Point Harbourview 2 bedroom pet-friendly home with disabled facilities.
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Linley Point Harbourview 2 bedroom pet-friendly home with disabled facilities.
Sydney, NSW
5% off
Price is AU$1,183
AU$1,183
AU$169 per night
includes taxes & fees
Image gallery for Tamarama Vista By The Beach
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Tamarama Vista By The Beach
Sydney, NSW
9% off
Price is AU$6,122
AU$6,122
AU$875 per night
includes taxes & fees
Image gallery for Bamboo House, LUX 3BR house close 2 City/beach/airport/train Staion
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Bamboo House, LUX 3BR house close 2 City/beach/airport/train Staion
Sydney, NSW
8% off
Price is AU$2,657
AU$2,657
AU$380 per night
includes taxes & fees
Image gallery for Private Studio below Stunning Heritage Cottage with own entrance
1010 out of 10 rating
Exceptional
(41 reviews)
Private Studio below Stunning Heritage Cottage with own entrance
Sydney, NSW
9% off
Price is AU$997
AU$997
AU$142 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Castlereagh Street
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Find the best place to stay - Castlereagh Street
Secluded Surry Hills Escape with Private Balcony
Sleeps 2 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
STUNNING SYDNEY HOME 1
Sleeps 4 · 2 bedrooms · 1 bathroom
7.47.4 out of 10
Goodgood
3 reviews(3 reviews)
Darling-of-Darlinghurst - Home with charm & History
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
CBD Center Gem | Modern 1-Bedroom Apt
Sleeps 3 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
KozyGuru | Haymarket | 2Bed 2Bath Apt
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
Oasis 4BR House/Darling Harbour&Casino-7 mins walk
Sleeps 10 · 4 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
3 reviews(3 reviews)
Top rated rentals - Castlereagh Street
City 2 Surf Getaway
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
The place was well positioned at North Bondi (ran past on the C2S run) close to Bondi.The place was spotless and well set up for our family including 3 adult children.Would definitely stay again.
Paul Green
Stayed Aug 2025
A perfect central location
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Stayed here for 2 nights while in our short family holiday trip to Sydney,and it exceeded our expectations! The apartment is bright,specious and well maintained with a nice views.would absolutely stay again-great value for the price!
Leela R.
Stayed July 2025
Wow!
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
This property exceeded all expectations! Our book club had the best weekend getaway here. Marc was a brilliant host and went above and beyond to make us a comfortable as possible. Thank you so much! We loved it.
Eynas B.
Stayed May 2025
Great location
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
We had a great time at the property. The house was exactly as described, the kids had a great time. The house was in a good location and it was easy to get around the city. Plenty of choice for cafes, restaurants and bars around.
Jessica P.
Stayed May 2025
Highly recommended
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
The accommodation was beautifully renovated & decorated, spacious, and immaculately clean.Location is straight opposite the beach and in walking distance to everything.Both the host and the property manager were very helpful and a pleasure to deal with.Would stay there again and highly recommend.
Stephen N.
Stayed Mar 2025
Family getaway
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
We could not have been happier or more comfortable during our stay. The house was spacious and very clean.
The toaster was broken, a new one arrived within hours.
Helen was delightful, and very accommodating. Highly recommended this property.
Catherine H.
Stayed Nov 2024
Great stay
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Had a great week here. Host was very accommodating
Jack K.
Stayed Oct 2024
Fantastic and very good location
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Guidelines provided were easy to follow, comfortable stay and location is very close to shops and Bondi beach. Good experience all round
Neville B.
Stayed Oct 2024
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value