50 Best Vacation Rentals in Woollahra - Holiday Lettings - Cabins

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Edgecliff
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Woollahra

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1,342 Vacation rentals

9

Vacation home in Woollahra

Sydney / Woollahra

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Beautiful 3-bedroom multi-level apartment in leafy Bellevue Hill with harbour views and sheltered garden. Very well located, just a short bus ride or walk to Bondi Junction and walkable to Bondi beach or Rose Bay, giving easy access to the city. Ideal for families or 2 …see more

from $350 / night

$2,445 - $2,988 / week

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from $350 / night

6

Apartment rental in Woollahra

Sydney / Woollahra

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
- Beautiful leafy suburb close to shops - Parking - WiFi - Strictly no children & no pets - Strictly no subletting without prior written approval from The Apartment Service. Large one bedroom apartment with courtyard. Minutes to Oxford St and Woollahra village lifesty …see more

from $102 / night

$713 / week

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from $102 / night

12

Vacation townhouse with shared pool in Vaucluse

Woollahra / Vaucluse

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This spacious family townhouse is located in idyllic Diamond Bay, Vaucluse . Close to shops, cafes and transport as well as some of Sydney’s most scenic and breathtaking parks and harbour beaches. Featuring 3 bedrooms, 2.5 bathrooms and 2 outdoor entertaining terraces, …see more

from $173 / night

$1,205 / week

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from $173 / night

(6) Excellent 

22

Vacation home in Woollahra

Sydney / Woollahra

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Car not necessary
Ideal for couples, business travelers, families (with kids & extended family) & within 10 mins walk to Bondi Junction Westfield Mall, Bondi Junction Station, Double Bay, Cooper Park Tennis. 10 mins drive to Bondi Beach, Watson's Bay, Paddington, Sydney CBD, Sydney Opera …see more

from $537 / night

$3,782 / week

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from $537 / night

(1) Excellent 

19

Vacation villa in Edgecliff

Woollahra / Edgecliff

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
Appreciate the very best of Sydney harbour life in this modern, one bedroom apartment which is ideally located opposite the crystal clear waters of Rushcutters Bay. This gorgeous apartment offers a true blend of sophisticated living with the relaxation and calmness affo …see more

from $142 / night

$1,179 / week

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from $142 / night

(1) Excellent 

16

Woollahra Vacation villa rental

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Experience Sydney from one of its most peaceful, convenient and picturesque locations, in this newly renovated Woollahra home. Whether you are looking to shop, eat, explore or unwind, you will find yourself in the perfect spot, just steps away from Queen Street's beauti …see more

from $134 / night

$1,045 / week

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from $134 / night

19

Vacation villa rental

Sydney / Woollahra

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Enjoy spectacular 270 degree harbour views, as far as the eye can see, from this stunning penthouse located in the exclusive boutique building 'Glenn Ascham' in Darling Point. This Penthouse offers the ultimate in luxury and comfort; and perfect for discreet VIP life …see more

from $498 / night

$2,651 / week

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from $498 / night

(1) Excellent 

19

Woollahra Vacation home rental

Sydney / Woollahra

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Pet friendly
Marvel at your elegant surroundings in this stylish yet sophisticated three bedroom cottage, located on one of Paddington's most quaint and wondrous streets. As you pull up to the charming red door and vine-swathed facade of this double fronted home, you will instantly …see more

from $232 / night

$1,891 / week

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from $232 / night

19

Vacation home in Woollahra

Sydney / Woollahra

3 4 5 nights min

  • 3 bedrooms
  • Sleeps 4
  • 5 nights min
Built circa.1904 this handsome Edwardian terrace has been lovingly restored and features many period furnishings synonymous with the era making this the perfect base for you to explore our amazing City. Situated in a prime location this three-bedroom two bathroom hom …see more

from $150 / night

$1,286 / week

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from $150 / night

17

Vacation home rental

Sydney / Woollahra

3 5 5 nights min

  • 3 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
Feel right at home in this fully furnished, architecturally designed three bedroom, two bathroom terrace that spans over three levels providing a vast space that is flooded with light from the many windows. The countless outdoor entertaining areas are a true feature of …see more

from $230 / night

$2,142 / week

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from $230 / night

18

Vacation villa in Woollahra

Sydney / Woollahra

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
Immerse yourself in the startling sights over our amazing harbour from every room in this one bedroom apartment in Darling Point. Whether you are in search of a restful retreat or visiting to reenergize, this home promises to be your perfect place to unwind and relax. …see more

from $134 / night

$1,205 / week

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from $134 / night

19

Edgecliff Vacation villa rental

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
Experience the absolute best of our beautiful city from this fully air-conditioned charming two-bedroom apartment. Situated in a lovely tree-lined street in the enchanting suburb of Woollahra, with a calming ambiance and true sense of elegance, this is a space that you …see more

from $192 / night

$1,473 / week

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from $192 / night

12

Vacation villa in Edgecliff

Woollahra / Edgecliff

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
Spectacular views from your lounge room and dining room windows will leave you feeling like you are sitting on top of the world in this fully furnished and well equipped one bedroom, contemporary apartment in stylish Paddington. Located in a tranquil setting, the bui …see more

from $115 / night

$1,179 / week

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from $115 / night

19

Edgecliff Vacation villa rental

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Enjoy this sophisticated two bedroom penthouse in the exclusive setting of Rushcutters Bay. With spectacular views over our beautiful harbour and the amazing collection of sailing and cruising boats moored in this famous marina - this is the ideal home if you like the v …see more

from $287 / night

$2,678 / week

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from $287 / night

(1) Excellent 

19

Vacation villa in Woollahra

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Situated in the heart of trendy, cosmopolitan Bondi Junction, this brand-new open plan contemporary apartment is part of the newly developed Aqua twin towers and is bound to be one of the most sought after pads in the Eastern suburbs. The ultra-modern home is compact …see more

from $268 / night

$2,276 / week

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from $268 / night

19

Villa rental in Woollahra

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
What a lifestyle! Be thrilled by all the wonderful inclusions available in this newly renovated, 2 bedroom apartment in Darling Point. North facing with idyllic views towards the boat-filled Bay and across the Harbour, this spacious apartment features a luxurious new ki …see more

from $192 / night

$1,553 / week

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from $192 / night

19

Home rental in Watsons Bay

Woollahra / Watsons Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
HOLIDAY PROPERTY: Celebrate in this property over the Christmas Holidays Immerse yourself in the Sydney Summer from this stunning four bedroom family home in exclusive Vaucluse, be greeted by a cool and calming ambiance which is created by the rich holiday feel and c …see more

from $612 / night

$4,285 / week

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from $612 / night

(1) Excellent 

16

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This bright, airy and functional top-floor apartment entertains spectacular views over three wonderful aspects of Sydney. With Rushcutters Bay in one direction, the city in another, and the rooftops of Paddington in the next, it is certainly a haven for anyone wishing f …see more

from $115 / night

$938 / week

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from $115 / night

28

Watsons Bay Vacation home rental

Woollahra / Watsons Bay

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask about children
  • Ask about pets
Wind down in style at this exclusive Art Deco Sydney harbour side idyll set within leafy surrounds, and just a casual stroll across to the picturesque Camp Cove Beach. Camp Cove Beach Haven is a private, secluded escape for families, situated in historic Watsons Bay at …see more

from $679 / night

$4,034 - $6,303 / week

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from $679 / night

14

Vacation villa in Woollahra

Sydney / Woollahra

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
Enjoy the tranquil surrounds of this adorable one bedroom apartment in the exclusive enclave of Woollahra. You will love the beauty of the stunning liquid amber tree that frames this quaint intimate block typifying life in this ever so elegant address. Once inside, y …see more

from $115 / night

$1,071 / week

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from $115 / night

10

Woollahra Vacation villa rental

Sydney / Woollahra

3 5 5 nights min

  • 3 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Pet friendly
The grand entrance from beautiful Rosemont Ave is a proud prelude what lies within this remarkable 3 bedroom, 3 bathroom over size apartment. Bathed in plenty of sunlight and offering house-like proportions, this magnificent apartment is a rare find within the highly so …see more

from $226 / night

$2,142 / week

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from $226 / night

19

Vacation home rental

Woollahra / Vaucluse

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Pet friendly
Harbour views, stylish interiors and perfect positioning to explore the rest of Sydney - this exquisite Vaucluse home has it all. Located near the foreshores of Sydney Harbour, the home is sunlit, spacious and perfect for a family stay, decorated in eclectic pastels an …see more

from $306 / night

$2,678 / week

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from $306 / night

14

Vacation home with swimming pool in Edgecliff

Woollahra / Edgecliff

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
You’ll want to savour every moment spent at Wallaroy with its tropical gardens, swimming pool and city views. Situated in the leafy eastern Sydney beaches suburb of Woollahra, Wallaroy is spread across two luxurious levels with an abundance of space and contemporary des …see more

from $1,227 / night

$7,298 - $11,167 / week

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from $1,227 / night

9

Woollahra Vacation home rental

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
Unusually wide cottage 50 metres from Queen Street. Featuring an unusually wide 6.85 metre frontage, this classic turn of the century cottage has been completely transformed by a stunning renovation, creating a wonderfully spacious, tasteful two-storey home. Set in a …see more

from $192 / night

$1,875 / week

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from $192 / night

(1) Excellent 

19

Edgecliff Vacation villa rental

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This exceptional apartment is set within the original mansion of an historic converted harbour front estate, gracing the shores of picturesque Elizabeth Bay. Built c1880s and named 'Beau Regard'. Now known as "The Palms', an exclusive collection of 14 luxury apartments. …see more

from $326 / night

$2,544 / week

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from $326 / night

32

Vacation home with swimming pool in Woollahra

Sydney / Woollahra

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Pearce St is the distinctive design you’d expect from the award-winning Tribe Studio practice. And you get a sense of that outstanding quality upon arrival at this peaceful bayside home. After parking in the garage, or in the driveway, you’ll find the entry via a privat …see more

from $1,390 / night

$9,184 - $9,454 / week

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from $1,390 / night

(1) Excellent 

19

Vacation home in Woollahra

Sydney / Woollahra

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
Experience the absolute best of our amazing city from this exquisite three bedroom, two bathroom terrace, situated in the fashionable hub of Paddington. This immaculately styled home is striking with elegant accents of grey and white and a hint of gold for good measure; …see more

from $245 / night

$1,875 / week

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from $245 / night

(2) Excellent 

19

Home rental in Woollahra

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This charming classic cottage built in 1841 offers a truly unique city experience in the heart of Paddington. It's only 50 metres from the famous Oxford Street so it's in the heart of the action and the perfect place for those looking to have some fun and explore this f …see more

from $173 / night

$1,741 / week

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from $173 / night

24

Vacation home with swimming pool in Woollahra

Sydney / Woollahra

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A magnificent view should be enjoyed from a comfortable chair in a beautiful room of a superb home and that is exactly how you will enjoy The Harbour View when staying in this opulent Point Piper home. Built circa 1920 with the curves, parquetry floors and high ceiling …see more

from $926 / night

$6,483 - $15,435 / week

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from $926 / night

15

Vacation home with swimming pool in Watsons Bay

Woollahra / Watsons Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
Located in the heart of Watsons Bay and walking distance to the famed Doyles Restaurant, this 3 bedroom, 2 bathroom luxurious home offers you the same view but is close enough for you to order take away. Bathed in sunlight right up until sunset this home not only offers …see more

from $2,316 / night

$16,207 / week

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from $2,316 / night

(1) Excellent 

35

Watsons Bay Vacation home rental

Woollahra / Watsons Bay

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
The Space Retreat to this exclusive location and enjoy this 1920’s Historic Beach Bungalow, only a 25 minute drive from the inner city and with transport links close by for you to jump on for a Sydney adventure or corporate visit. With waterfront location & spectacular …see more

from $772 / night

$5,403 / week

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from $772 / night

9

Vacation home in Watsons Bay

Woollahra / Watsons Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
It’s not just the fabulous harbour vista, private parking and convenient location that will attract you to this graceful home. Watsons Bay Cottage has its own unique personality that embraces you as soon as you walk up the stairs toward its soft ocean blue double fronte …see more

from $973 / night

$5,856 - $6,505 / week

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from $973 / night

24

Vacation apartment rental

Sydney / Woollahra

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This world-class Point Piper apartment is positioned in Sydneys billionaires playground and Australias most exclusive location. Sure to live up to all expectations, The Sienna boasts some of Sydneys finest harbour views in a setting of sophistication and elegance. Peace …see more

from $4,245 / night

$29,712 / week

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from $4,245 / night

19

Vacation villa in Woollahra

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
Perched on the peaceful waters of the Double Bay marina, this magnificent newly renovated apartment is the ideal hideaway combining luxury, style and convenience. The main open plan living and dining area combines woody features and natural-toned furnishings to creat …see more

from $230 / night

$1,875 / week

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from $230 / night

14

Vacation apartment in Edgecliff

Woollahra / Edgecliff

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
An art deco shelving unit with a few choice pieces greets you as you enter into this elegant and cosy two-bedroom apartment in a small block, opposite Rushcutters Bay which gives you the benefits of both waterfront living and being on the city’s doorstep. Ahead of you i …see more

from $284 / night

$1,789 - $2,161 / week

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from $284 / night

18

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
PRIVATE ROOF TERRACE with HARBOUR VIEWS Get swept away by this ultra-stylish two bedroom penthouse in the high class setting of Rushcutters Bay. With mesmerising views over the spectacular assembly of sailing and cruising boats moored in the famous marina and out to …see more

from $287 / night

$2,142 / week

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from $287 / night

21

Edgecliff Vacation home rental

Woollahra / Edgecliff

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set amongst established grounds this recently renovated grand Edgecliff home really is a true Sydney beauty. What we love We love the grand beauty of this magnificent period home, the superb renovation and the space and elegance it offers to guests. What the client l …see more

from $2,205 / night

$15,434 / week

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from $2,205 / night

19

Vacation home in Woollahra

Sydney / Woollahra

4 7 10 nights min

  • 4 bedrooms
  • Sleeps 7
  • 10 nights min
Urban living at its best, this spacious four-bedroom home designed by architect Alexander Tzannes, is only a short walk from Woollahra's Queen Street shopping village. This classic-contemporary house has a northerly aspect and parklands at the front and rear and boasts …see more

from $612 / night

$6,427 / week

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from $612 / night

15

Vacation home in Woollahra

Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This immaculate house is the perfect place for those looking to have a stay in Sydney. Located in the heart of Paddington just a few steps to Oxford Street and a short stroll to Centennial Park, Woollahra, Paddington Five Ways, Fox Studios and walking distance of Surry …see more

from $230 / night

$2,142 / week

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from $230 / night

16

Vacation home with shared pool in Woollahra

Sydney / Woollahra

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
If you’re looking for Sydney CBD accommodation that gives you peace and privacy, this incredible apartment for rent by owner is your dream holiday home. An Art Deco warehouse conversion that’s set in the treetops, the building is steeped in history (it was originally Mc …see more

from $393 / night

$2,477 - $3,020 / week

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from $393 / night